Deception

¹¹ The Traitor’s Tale

In the chaotic conditions of the former Soviet Union in the early 1990s, Herman Simm was a reassuringly solid figure. In January 1967 he had taken the standard pledge of the Soviet police force, ‘I, a citizen of the USSR, hereby taking the oath of the Soviet Militsiya, do solemnly swear that I will serve faithfully to the end the Soviet people, Soviet homeland and Soviet government.’ Since then he had a stellar record of competence and hard work. He had forty-four awards, including three medals for exemplary behaviour. At a time when brusque Soviet official manners still plagued public service, he was polite and pleasant. As well as Estonian and Russian, he spoke excellent German with smatterings of other languages. Unlike many officials from the old days, he counted as a patriot. As head of security at Toompea Castle, the country’s seat of government, he had masterminded its defence against an assault by pro-Kremlin demonstrators on 15 May 1990 – the closest Estonia came to an armed clash during its struggle to regain independence. By his account, if the defence failed he stood ready to escort the country’s then prime minister, Edgar Savisaar, through a secret tunnel to the town below, where a speedboat would whisk him to safety in Finland. Later he claims to have ferried Estonia’s hard-currency reserves in suitcases to safety in Helsinki for the nascent central bank, forestalling a possible Soviet attempt to seize them.¹

After independence was restored in August 1991 Simm moved onwards and upwards, becoming in early 1993 the regional police chief in Harju County, the area around the capital, Tallinn. That was one of the hottest beats in Estonian policing: as well as dealing with endemic organised crime, toxic waste spills and smuggling, his patch included a Soviet nuclear submarine training base at Paldiski, which was still out of the control of the Estonian authorities and had become a magnet for organised crime. Simm supervised the withdrawal of Soviet nuclear fuel elements and the handover to the constitutional authorities. Two months later, he became the top police officer for the whole country, where he showed a courtier-like ability to ingratiate himself with the powerful and the up-and-coming. In interviews with dozens of former associates, the adjective that comes up repeatedly is ‘helpful’. One not particularly close colleague was startled when Simm, having learned of his upcoming wedding, offered the services of a patrol car and two police officers to direct the traffic and organise parking.

In 1995, Simm moved to the Defence Ministry, initially to a low-key job as head of the analysis bureau, where he stood out as an efficient bureaucrat. The then Defence Minister, Andrus Öövel, said proudly that hiring a former police chief for the young ministry was like ‘winning the lottery’.² Few worried when Simm then added to his portfolio the handling of classified documents. It was an unpopular job: Estonia was plagued by scandals involving missing, supposedly secret, papers. Too many items were classified and the rules for safeguarding them were onerous and badly drafted. Simm’s bureaucratic habits, honed in the Soviet era, helped him sort out the chaotic paper flows inside a still half-baked bureaucracy. Estonia’s foreign friends, keen to see order prevail over chaos, quickly talent-spotted the new official as someone worth cultivating. Britain’s government (noting that his orientation was more towards Germany and Finland than to the Anglophone world) paid for him first to learn English at an intensive course at the Foreign Office language school and then to study security policy and practice at Chicksands in Bedfordshire, the citadel of Britain’s Defence Intelligence Service.³ On his return, he was a natural choice to oversee the ministry’s move to NATO’s security standards. His efforts received high marks: drills and tests showed Estonia’s ability to handle secrets to be first class – and indeed better than in some old members of NATO.

Once Estonia joined NATO in 2004, Simm, by now the ministry’s top security official, became a still more regular visitor to its Brussels headquarters. Although slightly handicapped by his stilted English – notably better suited to meetings than social events – his affable manner marked him out as one of the more welcome newcomers. Officials there remember an assiduous networker who used slightly heavy-handed flirtatiousness to good effect when dealing with female colleagues. He was prone to self-importance, seemed to feel that he was under-appreciated in Estonia, and liked to display a vocal anti-Russian streak. At home he oversaw security clearances, promotions and transfers for the country’s most important defence and security posts. He recommended people for courses in other NATO countries, and signed off on their requests to take part.

In Brussels, NATO saw nothing unusual. Simm met every criterion for the alliance’s top-secret clearance. A similar clearance at home was issued and checked regularly by Estonia’s Kapo (Security Police).⁴ But Simm’s record would have repaid closer scrutiny. Why, for example, had Sweden denied him a visa in the mid 1970s? His background, the result of a brief post-war liaison between a middle-aged lawyer and a young woman, then brought up by aunts, and having multiple marriages and partnerships in adult life, could have suggested personality flaws of the kind a canny intelligence officer can exploit. A Soviet-era police officer who had travelled regularly abroad could hardly have escaped contact with the KGB. Yet Simm had declared no such thing. That should have prompted both thorough scrutiny of the files and the question of whether he might be vulnerable to blackmail. In fact, he had had his first contact with the KGB Third Department (which dealt with military counter-intelligence) in 1968, as part of a routine sounding out of all recruits to the law-enforcement organs. Had the investigators dug deep enough in the KGB files (as they did later, once Simm was under suspicion), they would have found that the Soviet secret police formally recruited Simm in 1985, and that he had brazenly denied this collaboration in a declaration in 1992.

Even his post-Soviet career was dotted with suspicious peccadilloes. These included a jackdaw-like fondness for trinkets and souvenirs, collecting caps, pens, badges and plaques and even guns. He was an inveterate junketer, collaring any foreign travel opportunities available. His political views were unusual by Estonia’s sober standards. He had a conspiratorial and eccentric worldview, prone to believe that Jews, Masons and shadowy international organisations wielded huge power behind the scenes. Jüri Pihl (the then head of Kapo) and others also recall a surprising habit of bad-mouthing Estonia to visiting foreigners. These included the late Colonel Michael Scott of SIS, who had been involved in cleaning up the mess after Operation Jungle, and retained a deep interest in Estonia, returning frequently after 1992 to visit old agents and advise on security.⁵ Simm cherished photographs of such meetings, particularly prizing one showing a handshake with the head of Israel’s Mossad. Though not a real intelligence officer, he was clearly attracted by the glamour of that world, and always eager for gossip and news of the inner workings of Estonia’s spy agency. Indeed, some thought he might move to a senior position there after retiring from the defence ministry. His wife claims that he was even offered a job there.

Close scrutiny of his financial affairs by a suspicious counter-intelligence officer might have followed up gifts from a generous German relative, or his rather heavy use of cash. His lifestyle, in a country where senior bureaucrats are well paid but not wealthy, was on the lavish side, with a big house in a desirable village outside Tallinn, a large Western-made jeep for transport, and a summer house and other properties to his name. (He claimed simply to make good use of his travel allowances and to have regained property confiscated during the occupation.) His unorthodox treatment of official documents should also have attracted more notice. He habitually hand-carried secret papers to NATO HQ in Brussels, claiming that only he had the requisite security clearance. But against regulations, he would stay overnight at a hotel there before delivering them. On occasion, colleagues noticed that envelopes had been opened, unwitnessed.⁶ But such incidents were rarely logged and never followed up. As head of security, Simm made the rules – and if he chose to break them, presumably he had a good reason for doing so. To most people, Simm was not an impressive or mysterious figure, but a friendly and amenable bureaucrat, doing a dull job well. ‘I never thought about him as the National Security Authority,’ recalls Indrek Tarand, then a senior official and now a member of the European Parliament. ‘It was just Uncle Herman doing something funny.’

Even his earlier role in the defence of Toompea Castle in 1990 was not universally seen as heroic: some Estonians there at the time believe he gave himself a nosebleed as a sign of valour. Mr Savisaar recalls: ‘He was brought before me red in the face and shivering. He gave me the impression of a coward. So we fired him.’⁷ Jüri Pihl, who worked closely with Simm, describes his ability to deal with organised crime as ‘zero’. It was the steely young officers of his service (including one who later masterminded Simm’s arrest) who cleaned up organised crime in post-Soviet Estonia, not the then oafish and bungling officers of the uniformed police. In 1995 Mr Savisaar – then the Interior Minister in a coalition government – again crossed swords with Simm. He recalls a ‘somewhat theatrical’ red uniform ordered just for the force’s most high-ranking officers. ‘Like something out of an operetta,’ he says disdainfully. Simm was loyal, almost fawning. ‘Every morning he was sitting in my secretary’s office eager to report – but he could not cope.’ For a few months Mr Savisaar pondered how to dismiss his unwelcome subordinate. Then he summoned him and spoke of a ‘serious problem’, while laying his hand on a large file labelled ‘Herman Simm’ which was actually full of old newspaper. To his relief, Simm immediately resigned. ‘I was a little surprised that he then got a job at the Defence Ministry,’ says Mr Savisaar drily.[67]

To be fired twice by a hate-figure is a strong recommendation. The hawkish officials of the defence and security establishment had long loathed Mr Savisaar, seeing him as a cynical and greedy machine politician with unhealthily close ties to the Kremlin. If Simm was their enemy’s enemy, his foibles were irrelevant. Behind the scenes, some did worry. Security officials at the Foreign Ministry made a point of refusing to let him see diplomatic telegrams. The Defence Ministry’s internal counter-intelligence service clashed with Simm on occasion, but its efforts to constrain his unorthodox habits were undermined by a conspiratorial and bungling approach: it once attempted to put several senior figures in the ministry under surveillance, supposedly as an exercise. It was easy for the self-assured Simm to arrange for such jumpy and troublesome junior officials to be fired, transferred or ignored.

Simm was a happy man as his career peaked. From his bleak and humble upbringing in the Stalinist era, he had made a successful career not only in the Soviet system, but in the one that had replaced it. On 20 November 2006 a press release marking his retirement (one of several documents mentioning him still on the Estonian Defence Ministry’s website in mid 2011)⁸ gives a ghostly reminder of the esteem in which he was then held. It praises the organisation he built up as ‘effective and efficient’; and notes that he signed agreements on the protection of classified information with nearly twenty countries. The Defence Minister added that without doubt Simm had shown ‘excellent professionalism’. He also received praise from the then director of the NATO Office of Security, Wayne Rychak. Yet had any of his colleagues known the truth, they would have arrested him on the spot – for nearly thirteen years the avuncular, dependable Simm was an agent of the SVR, Russia’s foreign intelligence service.

Simm was one element in the human minefield left behind in the former Soviet empire amid the collapse of communism. The nature of these devices varied widely. One kind were former dissidents, often now in influential positions, who had been protected from their own countries’ secret police by their KGB connections. Some also had sincerely cultivated ties with the Soviet authorities in the belief that Mr Gorbachev’s reforms offered the best chance of bringing change to their own stagnating societies. Another component was people who feared German hegemony in Europe, or who were sceptical of American intentions. Such feelings – as in Simm’s case – were sometimes compounded with jealousy at the rise of smooth young Atlanticist types to senior positions. A big latent category was officials from the old regime with undeclared KGB or secret-police connections. Many of the files containing such details were destroyed after the collapse of communism (typically as part of energetic efforts by the new leaders to conceal their own collaboration). What was left behind was deliberately muddled, so that it was unclear even whether the names listed were victims of the totalitarian system, or its accessories. This created a false sense of security for many who moved on to good jobs in the new system. They did not know that before communist power collapsed the KGB had removed its own records, and copies of the most important files belonging to other agencies.

As a result, the KGB ensured that even after the Soviet empire collapsed, it, and only it, had an accurate record of who had collaborated and why. This has provided Russian spymasters over the past two decades with a unique ability to blackmail and pressurise seemingly impeccable figures in post-communist public life, who believed that their guilty secrets were forgotten or buried. Suspicions in some countries swirl around household names – heads of government or of state, ministers, newspaper editors, academics and tycoons. But the fact that such connections are even rumoured makes them less dangerous. For someone in the public eye, cooperating with the secret service of a foreign power is risky and conspicuous. Russian spymasters may gain some secrets from them, but they can exert little influence through them. More damaging are senior second-rank figures out of the public spotlight, especially in the security world like Simm. They not only know secrets, but are also in a position to cover their tracks. They are thus archetypal targets for Russian intelligence.

A 141-page classified NATO report calls Simm the ‘most damaging spy in the alliance’s history’. He unveiled the alliance’s innermost secrets, from the content of meetings to the details of its most important codes. He gave accounts of the arguments that raged inside the alliance about Russia, about the relative strength and weaknesses of different countries, and psychological assessments of its senior officials.

The real harm, though, was less in the actual secrets he revealed during his time as a spy, as in the breaches of trust with the NATO alliance that arose after he was arrested. For many of the old members, Simm’s treachery confirmed their worst fears about its eastwards expansion to countries that had so recently been under the Kremlin’s thumb. To them it seemed that the new member states were simply untrustworthy, riddled with Russian spies and incapable of keeping secrets. The idea of a ‘core NATO’ of seasoned West European members able to work closely together had never been fully buried during the alliance’s expansion to the ex-communist East. The news of Simm’s work for the Russians revived the discussion. For the new member states themselves the sense of distrust was different. Simm’s parallel work for German intelligence (of which more later) confirmed fears of big-country machinations over their heads, not just in Estonia but also in other countries. Were German agents also at work stealing secrets in Warsaw, Prague, Budapest or elsewhere? Before Simm’s arrest the idea would have seemed preposterous: Germany had presented itself as a solid ally for the ex-communist countries, always at pains to stress that its special relationship with Russia did not undermine its commitment to its immediate neighbours’ security. The new members now came to believe that was a lie.

Simm’s ability to operate undetected in the heart of Estonia’s much-prized new security system also raised painful questions about the competence and integrity of those who should have checked him. What had the NATO spycatchers been up to? How come they had not asked Simm properly about his career in the Soviet Union? Someone of his age and background, however affable and competent, should have been a candidate for special scrutiny. Yet the checks had always been superficial. With little more than bluff, Simm had been able to escape the tightest security in what is supposedly the world’s most formidable military alliance. And what about Estonia, which prides itself on keeping its security establishment free of any ex-Soviet taint? Simm was quite unlike the bright, clean-cut, English-speaking young officials who hold most of the top jobs in Estonian public service. During the 1970s and 1980s, they were only children. Simm was already a grown man then – and necessarily more vulnerable to KGB pressure. That should have raised hard questions, which the incomplete and misleading ‘official version’ of the case leaked by Western officials fails to address. Did Simm have a powerful protector? Was his escape from scrutiny mere incompetence, or perhaps something more sinister? How was he recruited? What did he betray? How was he caught? And why did it take so long? These questions are corrosive and troubling, and have remained unanswered to this day. The answers involve not only secrets, but lies and blunders. Even Simm himself does not know the full truth, and would not (or could not) speak frankly to me about what he does know. But without his account, mine would be incomplete.

It is rare for an outsider knowingly to meet a spy, and almost impossible to meet a jailed one. Once the interrogators have squeezed their subjects dry and damage-control officers have done their work, the traitor is left to a life behind bars. Spycatchers may be proud of having hunted down their quarry, but it is also their fault that the breach happened in the first place. They may worry too that the convict will try to send a coded signal to his former masters: perhaps that he has successfully concealed some vital piece of the puzzle, or has planted a particular piece of disinformation. From the authorities’ point of view, the less said to the outside world, the better. So getting to see Simm took some doing. Arrested in 2008 and jailed in 2009, he is serving a 13-year sentence in a maximum-security prison in Tartu, Estonia’s second city. Many Estonians hope he dies there. Even my close friends in Estonian officialdom were worried by the idea that an outsider with no security clearance, writing a book that would not be vetted by the Estonian authorities, could visit the country’s most notorious prisoner. Simm had outsmarted his colleagues over a period of many years. Maybe he would have some more tricks still to play. Another reason for Estonian caution was embarrassment. Simm’s conviction was a brilliant piece of work by the country’s spycatchers and their foreign colleagues. But the sooner the affair was forgotten about, the better for Estonia’s reputation.

My counter-argument prevailed. Estonia aims to be the epitome of clean and open government. It should deal with the Simm case according to principle, not convenience. But practicality played a role too: concealing Simm would stoke conspiracy theories and look defensive. Sooner or later a Russian author or newspaper would be able to make contact with him and write him up as a victim, or hero. My book would put Simm’s treachery in a broader and more informative context. The result of some hard haggling was exclusive, repeated access to Simm. An official of Estonia’s security police, whom I agreed not to name, sat in on our meetings and interrupted if we strayed on to topics he regarded as sensitive (Simm seemed frustrated by this, but when I reached him later by telephone, he remained reluctant to provide any significant further information, claiming to be too frightened). I insisted that I would write what I wished: I provided no guarantee that I would submit any portion of the manuscript to any outsider; nor did I promise any veto on its contents (though I have of my own volition omitted a few names and blurred some dates).[68] The only big point on which I failed to reach agreement, despite repeated requests, was to be allowed to make a recording of the meetings.

It was therefore with pen and notebook that in June 2009 I took the bumpy train from Tallinn to Tartu to meet Simm face to face for the first time. The prison underlines the progress Estonia has made in the past twenty years. Soviet prisons were grim, smelly and dark. Tartu’s clean, light design, with smooth concrete walls and yellow doors, could be anywhere in the Nordic region. Male prisoners were exercising in the yard, with Estonian pop music blaring from loudspeakers. The sight was oddly Soviet. It took me a few seconds to realise why. In the days of the planned economies, clothing was hideous in both colour and cut. The inmates’ baggy brown tracksuits, with orange stripes, were the sort of apparel you might have found in a Soviet department store in around 1985. Then it would have been the height of fashion. Now the garb is designed to make escaped prisoners conspicuous. Yet nothing short of a military attack would spring Simm: before reaching the interview room in the high-security wing of the prison, we passed eight doors, all opened only with cards, plus two passport checks and a metal detector.

For a man who prided himself on his personal grooming, Simm cut a sorry figure: pasty-faced, ill-shaven and with a faint whiff of sweat. Only his oily quiff of silvering hair seemed to have survived the indignities of his imprisonment. He claimed, belligerently, that he was expecting his lawyer, not an author. His first words to me set the tone: ‘So, you work for MI6.’ Lecturers at his courses in security at Chicksands, he maintained, had told him that all leading British foreign-affairs journalists are in the spooks’ pay. I countered that if so, I would not need to be asking him all these questions, as I would know everything already. He grudgingly accepted that. But the multi-dimensional battles of wits in the many hours that followed were the most challenging of my thirty years in journalism. My object was simple: to get from Simm the real story. The minder’s job was to forestall any detailed discussion of classified information, procedures or intergovernmental cooperation. Simm’s agenda was partly self-aggrandisement and partly to get money for his wife.⁹ Distinguishing fact from fiction in his account was hard. It featured confident, conspiratorial and eccentric assertions on everything from the prevalence of homosexuality in Britain to Freemasonry in Estonia. He habitually overstated his own role and denigrated that of others. Checking his veracity is hard. A lot of the material is secret. Some events are long ago. Other people involved have their own reasons for keeping silent, or can simply contradict Simm’s version: after all, who will believe the word of Estonia’s most-hated prisoner? Repeatedly and without exception, he skirted over any personal wrongdoing. He portrayed himself partly as a victim of the machinations of great-power politics; but also (quite contradictorily) as a man of destiny, who made the world safer by keeping everyone informed.

His descent to treason began, according to him and to Estonian officials, during a summer holiday in the Tunisian resort of Sousse in July 1995. A familiar figure approached him in the street. It was Valeri Zentsov, a former official in the Soviet Estonian KGB. Casually dressed in a T-shirt and shorts, he introduced himself, pressing Simm to join him for a vodka. This meeting was no coincidence: when an intelligence officer pitches to a potential agent, every aspect is worked out in advance. What are the target’s weaknesses? What happens if he threatens to report the encounter to his authorities? What mixture of bribery, threats and flattery will work best? That the Russians had identified Simm, and knew his movements well enough to approach him when he was on holiday, in between jobs, and following the end of his relationship with a much younger girlfriend, suggests a thorough knowledge of the comings and goings of Estonian society. Simm himself believes that a Russian mole elsewhere in the defence or security establishment had ‘spotted’ him as a likely prospect. That may well be true. Yet it is also possible that the story is in whole or in part a fake. No external corroboration for it exists. The real truth may be that Simm needed not to be recruited, but just reactivated.

Zentsov greeted him (at least according to Simm’s version of events) with pleasantries. Simm recalls:

Simm claims that the approach came at a time when he had survived bruising encounters with organised crime gangs in Tallinn. He recalls:

Zentsov assured Simm that Russia had no hostile intentions to Estonia, dismissing the (then only occasional) outbursts from Moscow as a mere ‘political game’. But he said his superiors were worried that NATO would use the small country as a base for an attack on Russia. That concern, Simm says, was a hallmark of Russian demands for intelligence over the next thirteen years. ‘Even at the last meeting, they were worried about NATO bases in Estonia.’

The natural thing for a patriotic Estonian to do – even a nervous and unemployed one – would be to listen politely and then report this encounter immediately to the authorities. Simm did not, apparently because Zentsov threatened to expose his collaboration with the KGB in the 1980s. Yet the threat was matched by an appeal to Simm’s self-importance, and his dislike of Estonia’s young, pro-Western, English-speaking security elite. He says elliptically of his decision to commit treason:

Traitors typically salve their consciences with the idea that they are playing a great role in geopolitics. Simm seems to have been no exception. The Russian also played skilfully on Simm’s troubled psyche, presenting himself as a similarly apolitical colleague. ‘He was a patriot and I was a patriot,’ Simm says, without irony. Zentsov stressed a common disdain for politicians, bemoaning the sleaze and abuse of power of the Yeltsin era, while also undermining Simm’s view of Estonian statehood. Did he know, asked Zentsov, that Estonia’s pre-war military leader, General Johan Laidoner, had worked for Soviet intelligence? And that the country’s then president Konstantin Päts had been on the Kremlin payroll too? Most Estonians would regard these ideas not just as fanciful but outrageously insulting. President Päts died in a Soviet mental hospital in 1956, where he was incarcerated because of his persistent belief that ‘he is a president of Estonia’. Laidoner died in a Soviet prison in 1953. Comparably absurd allegations would be to say that Winston Churchill was a Soviet agent, that FDR took money from the Nazi Party, and that General Douglas MacArthur had been in the pay of Chinese intelligence during the Korean War. But they chimed with Simm’s weakness for conspiratorial explanations.

With a classic mix of money, blackmail and flattery, the pitch worked. Simm agreed to cooperate with Russian intelligence, not as traitor but (he insists) as an officer, with a clandestine rank, salary and pension. That played on a grudge: that the Defence Ministry had never given him the military rank – equivalent to his position as a police general – that he believed he had been promised on joining. Simm claims he also insisted that he would never work against Estonia’s interests (as defined by him). The offer and promise alike were delusions, but Simm’s value for the SVR was all too clear: a trusted, well-connected source, in the heart of the country’s burgeoning defence establishment. Running the new agent was easy. With his KGB background obscured by his status as a ‘military pensioner’, Zentsov had no difficulty in visiting Estonia, though most of the contact with Simm took place in third countries.[69]

Everyone involved in Simm’s rise through the Defence Ministry bureaucracy is eager to blame someone else. But the new recruit’s experience at the outset was of profound disappointment. Used to the established bureaucracy of the police force, he found only empty desks, bare walls, intrigues and chaos. He was also unconvinced about the whole idea of defending Estonia by military means. British advisers, he recalled, told him that resistance to a Russian attack would last ‘just four hours’ – the time it would take for tanks to get from the border town of Narva to Tallinn.

Simm’s initial haul of Estonia’s defence information was correspondingly scanty. Estonia in 1995 had practically no armed forces, slender military relationships with other countries, and seemingly scant chance of joining NATO. The biggest target for the Russians was Western intelligence cooperation, about which Simm could make only informed guesses. What he could offer were insights into the Estonian elite: who was up, who was down, who was facing a financial or marital problem; who was being trained in what specialism by which friendly country, how deeply, where and when. In one security exercise, supposedly to help the ministry get ready for NATO membership, he grilled staff with sixty questions covering private hobbies, plus possible weaknesses ranging from sex and alcohol to cars. Although he did not have access to the full ‘confessionals’ of Kapo’s counter-intelligence interviews, in which senior officials have to explain the details of any sexual or other entanglements that could make them vulnerable to blackmail, he would have had a good idea about their conclusions. His knowledge of crisis management plans was also damaging. The Estonian elite is small, with perhaps two hundred people in the key decision-making roles. Many have served in senior positions in several different ministries or agencies – defence, interior, security, the police, the diplomatic service and intelligence. Many of them are trained to stand in for colleagues in an emergency. These carefully made plans were laid bare to Russia. Should it want to decapitate Estonia in future, it knows where to strike.

Simm’s tradecraft instructions were straight out of the Soviet KGB’s playbook. He placed films, and later memory sticks, into small juice cartons of a particular brand and colour and threw them away in rubbish bins in designated parks. Each dead-letter box was used once only. By his own estimate, he met Zentsov sixteen times in ten different countries. But here arises one of the big mysteries of the case: the exchange of information. Simm insists, in multiple interviews, that the relationship with Zentsov was not a one-way street: 40 per cent of information flowed from him to Zentsov, 60 per cent the other way round. But what was that incoming information? And what did Simm do with it? During my interviews with Simm, the Estonian minder resolutely kept that subject out of bounds, and Simm himself subsequently claimed to be too scared to discuss it when we spoke on the phone.

That is rather tantalising. If he truly passed on information, Simm would inevitably be quizzed about its source. Any intelligence service would wish to double-check it. Any counter-intelligence agency would be deeply alarmed by a senior official meeting a known spy from a hostile country; it would allow such contact to continue only under the closest scrutiny. Simm claims that he would have liked to confide in British or American intelligence but was too scared to do so. ‘I did consider telling someone,’ he says, while insisting: ‘But I used that material and passed it on.’ But what material, and to whom? Whether Simm’s claim of a ‘two-way street’ is self-delusion, mischief making, or a fragment of a bigger story remains one of several unsolved puzzles. Others are even more intriguing.

Zentsov was an old-style spy: a hardened KGB veteran from Soviet-occupied Estonia. While he was guiding Simm into the heart of the Defence Ministry, a new Russian intelligence presence was developing in the region, in the form of Antonio Graf, a plump, bearded man from Madrid. Apart from his slightly exotic middle names (de Jesus Amorett) he cut an unremarkable figure in the Baltic states. A Portuguese citizen, born in Brazil and working in Spain, he was one of thousands of consultants and go-betweens getting to know the continent’s new eastern frontier lands. Until 1989, West European businesses had been almost wholly ignorant of the markets and suppliers behind the Iron Curtain. Dealing with the communist bureaucracy involved marathon negotiating sessions, best conducted with strong government support. Shortage of hard currency made customers stingy; NATO controls on the export of sensitive products meant that the deals that looked most promising were probably illegal. When communism collapsed, most businesses were initially deeply sceptical about the new markets. Would bills be paid? What was the work ethic? Could the communists come back? Would civil war and chaos spread from the Balkans? What about organised crime? And corruption? Even the most basic data about household income, family structure, education levels, property rights, currency regulations and the like were unknown.

So Antonio (as he was known to his many acquaintances and contacts) sounded completely plausible in his many trips to the Baltic states, which seem to have started in the mid 1990s. He assiduously collected information about business conditions and the political and economic outlook, apparently spending some years building his ‘legend’ as a regular and credible visitor before engaging in any spying. His mission seemed anodyne and convincing. One contact recalls:

People who met him recall nothing suspicious, and little that was even distinctive, except possibly his odd choice of tipple: a revolting mixture of Campari and tonic. Anyone suspicious about his motives or background would have found it hard to check them. Spain and Portugal, and their languages, were all but unknown in the Baltic states in the 1990s. If his Spanish sounded faintly accented, that would be because he was Portuguese. If a Portuguese speaker noticed a stray syllable, the answer was that he was born in Brazil – which from a Baltic point of view could have been the far side of the moon. The idea that he was in fact a Russian intelligence officer named Sergei Yakovlev, working under an elaborately constructed illegal identity, would have seemed paranoid fantasy.

When Zentsov retired, it was Antonio who took over as Simm’s case officer. Relations were poor from the start. Zentsov had excellent tradecraft and good people skills. Antonio did not. He was already known to Simm as a postman, handling the huge amounts of classified material that the Estonian was passing to the Russians. They had met once at a suburban railway station outside Tallinn. But Yakovlev was a curious choice of case officer for a source of Simm’s importance. He appears to have broken several cardinal rules of Soviet spycraft. The cost of establishing a fully fledged illegal in a NATO country is considerable. Creating an identity for Antonio involved obtaining the birth certificate from Brazil, using that to obtain a Portuguese passport, and then establishing a convincing pattern of activity that would take him to the Baltic states when necessary. In the austere world of the KGB, his only task would have been to run Simm: meeting him in carefully chosen locations either with proper clandestine preparation, or openly in a way that fitted both men’s natural pattern of activity.

But the Russian was clearly being used for other purposes too. A good illustration of his approach comes from Ivar Tallo, a distinguished Estonian official who has helped make the country a world leader in ‘e-government’ – putting public administration online. Mr Tallo recalls meeting Antonio rather reluctantly in 2001, as a favour to a friend and colleague in high office. That was nothing unusual: foreign visitors were flooding into the Baltic states as the reborn countries’ economic and political importance grew. Senior officials could not possibly meet them all, and a persistent Portuguese consultant would be quite likely to be farmed out to someone less important. At any rate, Mr Tallo chose an expensive Italian restaurant in Tallinn, on the reasonable assumption that he would at least get a decent meal in exchange for his time. Two more meetings followed. Antonio quizzed Mr Tallo on Estonia’s politics and economics, showing no particular interest in his specialty of e-government or associated questions of cyber-security. At the third meeting he suggested formalising the cooperation on a commercial basis. He suggested that Mr Tallo set up a company offering political and economic forecasts, for which his clients in Portugal would be prepared to pay handsomely; to underline the point he pressed an envelope of cash on Mr Tallo as an advance payment. The Estonian politely declined. He did not want to be obligated to the persistent Portuguese and found the offer of money slightly disconcerting. Truthfully, he explained that he was simply too busy to take up the offer. His interest was in e-government, not business information. Antonio never contacted him again.

The approach is straight out of an intelligence playbook. First hook the fish, then reel him in. Money creates a relationship, then an obligation. At some point the material asked for becomes less anodyne and more sensitive. Before the victim is fully aware of what has happened, he is enmeshed. Then comes the offer of still more money for really interesting information, and perhaps the threat of exposure in the case of non-cooperation. Mr Tallo was never close to that danger, and reported the encounter to the Estonian authorities as soon as news of the spy’s real identity broke. Fatefully, Antonio tried a similar approach with a senior Lithuanian public figure a few years later, arousing the interest of that country’s then formidable counter-intelligence service.[70] It remains unclear where else he tried his persuasive tactics, and with what result. As late as 2010, Latvia’s spycatchers were still following up leads dating from his regular trips to Riga. Yet Antonio was failing in his primary duty: to run Russia’s key Estonian source securely and efficiently. Simm instantly distrusted his new case officer, referring to him as a soplyak – a derogatory Russian word for an incompetent beginner that translates roughly as ‘snotnose’ or ‘wet behind the ears’.

After a botched first meeting with Simm in Cyprus, distrust turned to loathing. Simm says his case officer was ‘lightweight and arrogant’: snooty, rude and worst of all careless. The Russian was greedy too. ‘When we met I would eat a small fish dish. He would have steak and red wine,’ Simm recalls in a characteristically petulant aside. He assumed that Antonio was fiddling his expenses and doubted that the Russian was a fully trained illegal; his cushy job, Simm suspected, stemmed from connections not talent. That is consistent with the theory that nepotism is rife in Russian intelligence (a theory also supported by the way the lightly trained Ms Chapman gained a plum posting in the West). In his last meeting with Zentsov, Simm had complained about the new man, only to be told that Antonio was the best available: the SVR, Zentsov maintained, had only a couple of illegals in all of Western Europe.

A more tough-minded agent might have gone on strike at this, demanding a serious handler. Astonishingly, given the risks he was taking for the SVR, Simm settled for a stipulation that meetings with his case officer should be held only outside Estonia. Communication between the agent and source was simple. Simm continued to hand over his material via dead drops, using a more sophisticated digital camera, flash drives and memory cards, sometimes concealed in a pill container with a false bottom. He received, in cash, a ‘salary’ of €1,000 a month, plus expenses. The two men met fourteen times in total, mostly in the Baltic region but sometimes farther afield. By Simm’s account, only Germany, Norway and Britain were off limits. They arranged their sessions via a Prague-registered pager account, with simple numeric codes to send and receive messages. The number could be dialled from a public phone box. In retrospect, that might seem sloppy too. A central principle of spycraft is to make the source do nothing unusual. That would mean exchanging messages through means that seem like random variations in ordinary life: for example by using particular combinations of coloured ties, shirts and scarves. That would be necessary for Western spies operating in a police state like Russia; in the open environment of the European Union, Russian spymasters may have considered such precautions unnecessarily elaborate.

Simm’s productivity rocketed as Estonia joined NATO. He was party to the inner counsels of the alliance, attending scores of security-related meetings in Brussels and elsewhere. His own clearance was impeccable. ‘The Americans checked me, the UK people checked, the Norwegians, Germans, Denmark, Finland – all services checked me,’ he recalls. A big area of Russian interest was cryptographic security. Simm duly provided details of NATO’s top-secret Elcrodat network, a heavy-duty encrypted communications network used for secure messaging and scrambled voice traffic. During the Cold War, with a military conflict a real possibility, such a breach would have been catastrophic. But in peacetime, with the Soviet threat long gone, it is more embarrassing than damaging: most of the secrets that Elcrodat carried were non-secrets before and after they were fed into the system. Moreover, a key principle of cryptographic security is that if one encryption key is compromised, another can be used in future. An analogy is the combination to the lock on a safe: knowing it is useful only if something valuable is inside; and once the breach is known, the combination can be changed.

In short, it would be wrong to overstate the effect of Simm’s treachery on the overall balance of power between Russia and NATO. In an alliance of more than two dozen countries, security is never as tight as it seems. Among other NATO members are countries such as Greece, which have in the past proved leaky on issues of interest to Russia, and more recently Bulgaria. Given the activity of the GRU and SVR stations in Brussels and elsewhere, it is a fair bet that Russia was receiving plenty of other information about NATO too. Simm may have been a big source, but he was certainly not the only one. By Simm’s own account, he gave his SVR handler only ‘two or three things that were really important’ (he declines to say what they were). Paradoxically, Simm’s biggest betrayal in this regard may have been to reveal that NATO (at least at the time that Simm was spying) itself had so few secrets about Russia. When the alliance expanded eastwards, it did not draw up formal contingency plans to defend its new members, on the grounds that this would be provocative to Russia, and also unnecessary, as Russia was a friendly country.[71] America, with the support of Germany and other countries, explicitly barred MC-161, the top-secret NATO committee that draws up the threat assessment, from considering any potential military dangers from the East. When Poland protested about this in 2007, NATO chiefs reluctantly agreed that a threat assessment could be drawn up – but only for an invasion from Belarus, a country roughly a third of Poland’s size. NATO military commanders also quietly engaged in what they called ‘prudent planning’ – sketchy desktop exercises about how in an emergency the alliance might respond to a Russian threat.

All this would have been interesting for Russia – and valuable in the (almost inconceivable) event that it planned a military attack on the new member states of NATO. But it was not what the spymasters in Moscow wanted to hear. Their interest was in portraying the West as aggressive and intrusive, justifying the xenophobic rhetoric and paranoid worldview that allowed them keep a tight grip on power and its spoils. Consistent with that would be secret bases in NATO’s new members, with plans to attack Russia. Yet the harder that Simm’s taskmasters urged him to find evidence of nefarious NATO intent, the less successful was his search: the secrets he was seeking simply did not exist.

Simm also provided Russia with damaging insights into the weakness of NATO’s counter-intelligence efforts. These are severely hampered by political constraints: in particular Germany dislikes the idea of hunting Russian spies inside the alliance, and puts pressure on NATO Office of Security to soft-pedal investigations and not to act on the results. Details of that were most interesting for Russia’s spymasters. Simm attended two NATO counter-intelligence conferences, according to the damage control report. The German magazine Der Spiegel asserts that:

Simm’s other betrayals were more clearly damaging. The sixty-point security questionnaire he circulated inside the ministry, ferreting out officials’ hobbies, weaknesses and guilty secrets, would have been valuable information for a Russian intelligence officer looking for other potential targets. But even more interesting than this kind of information may be the rules that govern its collection. In the run-up to Estonia’s admission to NATO, Simm obtained the alliance’s procedures for issuing security clearances. An application is submitted, and either rejected, accepted, or (sometimes for a reason, sometimes at random) referred for further investigation. No explanation is offered. This basilisk-like stance is essential in preserving the integrity of the system. If you don’t know what to lie about, it is much harder to lie about anything. NATO at the time was dealing with many clearance applications from officials in the former Soviet bloc, and had decided that it would be unreasonable to say that former membership of the Communist Party was an automatic bar. For applications from Western Europe, such political activity, except possibly as a temporary student affectation, would have been an instant bar. NATO decided that a key disqualification for applicants from behind the old Iron Curtain would be attendance at a Higher Party School. These elite courses in the communist system’s internal university were attended by the ambitious and brainy, and thus a prime recruiting ground for the KGB. For a Russian spymaster trying to work out how an agent could penetrate NATO, that would be most useful information: those with Higher Party School education should either not bother to apply for a clearance, or else should see if this part of their past could be concealed.

Another use for Simm concerned Estonia’s help for Georgia and Ukraine, which for much of the last decade had hopes of joining NATO. The alliance was publicly cautious about their chances, which eventually flopped at a disastrous NATO summit in Bucharest in 2008. But a strong lobby in America had tried hard to boost their chances, not least by helping them reorganise their defence, security and intelligence services along Western lines. It soon became clear that advice from Estonia (and to some extent the other Baltic states) was particularly effective. American and British advisers knew the theory, but not the practice. Estonia had first-hand experience in judging which parts of Soviet administration were incorrigible, and which could be successfully transformed. An influential cabal of advisers in Georgia gained the nickname of the ‘Estonian kitchen’, after a senior Russian official complained publicly ‘we know this kitchen’. Russia could not stop the burgeoning cooperation between Tallinn and Tbilisi. But thanks to Simm it knew a lot about it.

Simm was also useful in keeping an eye on the relationship between Estonia’s intelligence agency and its NATO counterparts. The most sensitive operations were run on a purely bilateral basis. But NATO wish lists and some intelligence obtained did cross Simm’s desk. Clearly, the SVR was thrilled with their agent. As well as receiving a medal in 2006, Simm also met a senior officer – he believes a deputy director – of the SVR, in a carefully staged meeting in the western Czech spa town of Karlovy Vary. The two men walked in a park together, with Antonio keeping a discreet distance. This is standard practice in Russian spycraft when a source becomes particularly important: it allows the service to be sure that the case officer has indeed recruited the person he claims, and provides a check against embellishment, or the use of a double agent.

But long-term espionage operations, when successful, contain the seeds of their own destruction. Information obtained must be used, or the effort to obtain it is pointless. And using it creates clues for the other side. If you regularly see your opponent is forewarned, you wonder why and start taking measures to plug the leak. Simm’s case was no exception.

Indeed unease had been growing for years in Western capitals about Russian penetration of NATO. Initially, at the end of the Cold War, the guard had dropped. The prospect of a Soviet conventional assault on Western Europe, giving a few panicky days to decide between nuclear war and surrender, had shaped thinking for a generation, but with the military threat gone, and Russian forces in retreat from their former empire, thinking about security relaxed. That led to blunders – for example in the NATO operation in Yugoslavia in 1998, when a French officer at the alliance’s HQ, Pierre-Henri Bunel, leaked its military plans to Belgrade (and was jailed for it). As NATO tried to befriend Russia and treat it as a partner, it became easier for Russian spies to pitch to NATO officials: passing on a bit of information was no longer treason, it was just oiling wheels that were already turning. Russian espionage attempts played skilfully on jealousies and rivalries within the alliance. Some of those recruited by the Russians resigned quietly when caught, rather than face prosecution: nobody at the top in NATO wanted to seem too hawkish or provocative when the message from their political masters was to promote reconciliation and trust. That was annoying for NATO’s spycatchers. So too was the difficulty of screening officials from new members of the alliance (though attention focused on countries such as Hungary and Bulgaria, rather than the Estonians, who were seen as star pupils). But more troubling than all this were the agents the spycatchers could not find. Russia was clearly devoting considerable resources to penetrating the alliance, at a time when NATO’s counter-intelligence services had neither the capability, nor the political backing, to deal with it.

Similar worries were soon to be felt even more sharply at the top of British and American security establishments. Western human and electronic sources inside the Russian defence and security establishment suggested that huge quantities of documents, as well as details of cryptographic security and of high-level policy discussions on issues such as cyber-warfare and missile defence, were making their way into Russian hands. This was far more than the piecemeal collection of small leaks, gossip and chance disclosures that could be expected from normal espionage activity: the explanation could only be a major breach. Close scrutiny of the evidence suggested that the leak was in some way connected with the Baltic states. The finger of suspicion pointed either at a senior official in the region, or to one posted to Brussels. At the same time Western intelligence appears to have had a separate lucky break, recruiting a source in the heart of the SVR, closely involved in the illegals programme. The information was initially fragmentary and incomplete. But it still marked a breakthrough – the biggest, perhaps, since Vasily Mitrokhin’s archive – in finding Russia’s most elusive spies in the West. The spycatchers’ net was beginning to close at two ends: one around the blundering Antonio and his colleagues, and the other around the disgruntled Simm.

At this stage, Western spy chiefs took no action. It was more important to identify the leak than to try to catch the traitor. Once they knew the person or people involved, the time would then come to decide whether to prosecute, to hush the matter up, or to try some ruse in return. This reflects a paradoxical feature of counter-intelligence: that the seemingly most difficult business, of identifying a suspected spy, is in practical terms the least demanding. Collecting the evidence, especially if a prosecution is planned, is far trickier. The surveillance needs to be comprehensive but invisible, and must be conducted against targets trained to spot it. The slightest slip may end in disaster. Simm’s watchers knew that it would be all too easy for Russia to bundle their quarry into the back of a van and spirit him across the border. For MI6 to rescue Oleg Gordievsky under the noses of the KGB had been a hugely complex and risky operation. For the Russians to do the same from a Western country is easy. Antonio could board a plane from Madrid and never be seen again. Without enough evidence, you cannot stop a suspect escaping. But gathering the evidence is just what may prompt him to escape.

The spycatchers of the CIA’s counter-espionage division and a tiny group of trusted foreign partners took enormous care not to show their hand. Their aim first was to hunt down the prize catch of a Russian illegal, based on the tentative clues available. Where was he based? How had he gained his illegal identity? What was he up to? Who were his agents? Who was his controller? Would it perhaps be possible to ‘turn’ him and run him as a double agent within the SVR? Patience and subtlety would bring a reward: haste and carelessness would mean catastrophe. Then Antonio’s blunder forced the pace; the Russian’s attempt to solicit information from the Lithuanian alerted that country’s counter-intelligence service. Initially, they found the Hispanic-seeming visitor a puzzle. Was he perhaps a Western intelligence officer on an undeclared mission? Or from Israel’s Mossad? Or from China? The initial hypothesis was that he might be from the intelligence service of neighbouring Belarus. Then they observed him meeting Simm. That seemed to explain the affair: the mysterious visitor was clearly being run by those clever Estonians. But enquiries in Tallinn drew a blank. Discreetly, the Americans and Lithuanians compared notes and over a weekend in April 2008 separately briefed their Estonian counterparts: Simm, the most trusted official in the Defence Ministry, was a Russian spy.

A nerve-wracking period of ultra-discreet observation and analysis followed, involving at its peak counter-espionage officers of more than a dozen countries. One avenue was electronic: trying to snoop into the Russian’s computer in Madrid. Another was the paper trail: discreetly checking up on his documentation and aliases. A third was to obtain his DNA and compare that with databases of other known agents. Only a handful of people in Estonia knew the truth: their tricky task was to maintain absolutely normal relations with a man they once trusted, but now detested. An operational headquarters for the spy-hunt was established at a CIA base in a converted riding stable in Antaviliai, 20km outside Vilnius.¹¹

Simm claims that ‘one and a half years’ before his arrest he had picked up signs in NATO that the information he was passing to Moscow was attracting attention in the West. He sensed a change of atmosphere in Tallinn. And he believed (rightly) that he and Antonio had been under observation at a meeting in the Latvian capital, Riga. He says he tried, but failed, to make discreet contact with a Western secret service, presumably with an offer to be a triple agent: for whatever reason, this approach was rebuffed. In January 2008 Antonio reported to Moscow that his source was ‘in a panic’.¹² At the penultimate meeting in Stockholm later that year, Simm began to suspect that his Russian handlers were hanging him out to dry. While continuing to urge Simm to seek a job in Estonia’s foreign intelligence service, Antonio responded to his tales of woe with a blunt ‘that’s your problem’. He turned down his agent’s request for emergency exfiltration to Russia, and informed him that the colonel’s rank he had been promised when recruited was no longer available, let alone the major-general’s rank to which he believed he had been promoted. The system, Antonio explained blandly, had changed.

The disillusion was not sudden. Simm claims that he wanted to stop spying as early as 2005. After stepping down as the National Security Authority in 2006, he had worked as an adviser on special projects, such as organising NATO meetings in Tallinn, and handling Estonia’s contribution to the war in Afghanistan. He had made this career move – he says – without consulting Antonio, who had been furious when he heard. In his final meeting with Antonio in June 2008, Simm gave him a blunt message to pass to Moscow: ‘that I was retired, had no access, was not working’. He received no response, returning to Tallinn crestfallen and worried. Far from facing a comfortable retirement as a general in the SVR, he was a mere paid traitor, and a clapped-out one at that. His access to important secrets was gone; he was on the brink of retirement, and at risk of discovery. On 16 September 2008 Antonio then inexplicably compounded the danger by telephoning him on his mobile phone and cancelling a meeting, claiming to be ill. Simm’s phone was already tapped by the spycatchers of Kapo, which had secretly opened a criminal case on 26 May 2008, and had been collecting the evidence necessary for a treason trial. The trap was ready to be sprung.

The Rõõmu (pleasure) shopping centre in Keila is like many others in small-town Estonia. The supermarket boasts a good selection of wines (Estonians are fond of beefy New World reds), automatic checkouts (Estonians like gadgets) and a well-stocked cake shop. On 19 September 2008 Simm and his wife headed there to collect a three-kilogram kringel (iced cinnamon pastry) they had ordered to celebrate his mother-in-law’s upcoming birthday. As the couple emerged from the building carrying their shopping, they looked like any married couple preparing for a comfortable and untroubled family weekend. In the bustle of a Friday afternoon, neither of them noticed a black VW minibus parked discreetly near by, or the ambulance waiting around the corner in case Estonia’s most-wanted man violently resisted arrest, collapsed, or took poison. The Kapo officer[73] who placed them there was a seasoned veteran of the service’s toughest operations against Russian organised crime. But this arrest was to be the most important event of his career. It had been meticulously planned, in close cooperation with counter-espionage officers from friendly foreign services. Simm’s treachery was humiliating: a flawless arrest and prosecution would go some way to redress the balance. ‘We wanted it quiet, no conflicts and the goal was immediate cooperation,’ recalls the Kapo officer. The first moments would be crucial: ‘You cannot rewind if you make a mistake.’ Showing his badge, he approached his target: ‘I need a couple of words.’ Simm seemed unbothered: he knew the Kapo officer and assumed it was some minor query to do with security at the ministry. In a few seconds, Simm was sitting in the minibus, with his wife whisked away to a nearby car, where she was told ‘just wait quietly’. She assumed it was a mistake: her husband had not worked full-time in the Defence Ministry since April.

In the minibus came the thunderbolt: ‘Mr Simm – you are under arrest on suspicion of treason.’ Simm was familiar with handcuffs, but not with the sensation of being handcuffed. He started sweating, as he was searched for poison or other incriminating evidence. ‘I will speak. You won’t,’ continued the arresting officer. He produced a pile of papers, at the top of which were three pieces of evidence. One was from Simm’s KGB file, showing that he had promised cooperation in the Soviet era. Another was a picture of Simm making a phone call (in fact to his case officer’s pager) from a public telephone in the coastal resort of Pärnu. The arresting officer then informed him Kapo knew that Antonio was a Russian intelligence officer called Sergei Yakovlev. Simm cracked: ‘It had to happen sometime,’ he mumbled, ‘I didn’t expect you would come so soon.’ The prisoner and his captors went directly to Simm’s home. They found cipher pads (presumably used in radio messages), lists of dead-letter boxes and piles of classified papers (Simm claims that these were not for espionage, but material for a book of memoirs that he was planning to write). Simm also gave details of the memory cards he used to transfer information. The interrogation that followed by Estonian and foreign counter-espionage officers remains secret. But Simm appears to have put up little resistance. He pleaded guilty at his trial in February 2009 and has contested only the authorities’ attempts to seize his property.

A big puzzle in this is that an inviolable rule of Russian spycraft is that a second source, run by a separate case officer, must back up any important agent. The people involved are not (in espionage jargon) ‘inter-conscious’. They may know that their behaviour and intelligence product is being compared with a rival, but they do not know who, where, or how. This provides a powerful cross-check. If a source is tempted to embellish his material, it will stand out. If a case officer takes a short cut or exaggerates a difficulty, his report will be compared with that of a counterpart. This technique helps to deal with everything from fiddling expenses to a full double-cross. So where was the other Russian spy? The answer to this question depends on whether Simm’s prime target was Estonia, the Baltic states in general, or NATO as a whole. Matching his access to NATO documents would not be too hard, in an alliance of (now) twenty-eight members. Finding a similarly highly placed agent in Estonia, however, would be harder. Plenty of rumours surround this: according to one, Russia had another agent in the heart of Estonia’s security establishment, whose codename was Kask (silver birch). If this agent existed, what happened to him? He clearly was not prosecuted. I can find no convincing trace of a senior Estonian (or Latvian or Lithuanian) official having defected, disappeared, retired prematurely or emigrated mysteriously. Perhaps the evidence for prosecution was insufficient. Perhaps the person concerned made a full confession, switched sides, or decided to brazen out any enquiry. My own hunch is that the parallel agent was in a big West European NATO country and was unearthed around the same time but eased into discreet early retirement to avoid embarrassment. This agent could well have been run out of Brussels by one of the Russian intelligence officers later expelled from the Russian mission to NATO.¹³

Shortly after the excitement of Simm’s capture, another scandal broke: Simm had been not only a spy for the Russians but for the Germans. This aspect of his life is shrouded in secrecy. A handful of leaks to the German magazine Der Spiegel have painted a sanitised version of his cooperation, claiming that it dated from his days as a policeman, rather than in the Defence Ministry, and concerned chiefly Russian organised crime, rather than intelligence matters.¹⁴ Yet fragmentary clues suggest a darker picture. According to other officials in a position to know, Simm’s cooperation with the German BND spy service was deep and long-lasting, stretching at least up to Estonia’s membership of the European Union and NATO in 2004, and possibly even longer. In retrospect, the BND’s misbehaviour is less of a puzzle. After Estonia restored its independence, the absence of good ties with German intelligence was conspicuous. Some countries such as France were annoyed that the British had got their feet under the table so quickly and hurried to catch up. Sweden and Finland were the quickest to regularise their activities, with ‘declared’ intelligence liaison officers taking up postings at the new embassies in Tallinn. America too built up a large CIA station, which enjoyed correct if sometimes aloof relations with its Estonian counterparts. As well as with these countries, Jüri Pihl, head of Kapo from 1993 to 2003, recalls the excellent ties that his service built up with partner agencies in Austria, Norway, and later the Czech Republic and Poland.

Germany was the notable exception. The Baltic region had historically been Berlin’s shared backyard with Moscow. Relations with Russia, on everything from energy to migration, were vital. It is easy to see that senior German politicians would find it annoying that devious and interfering spooks from London were hooking up with a bunch of zealous and youthful Estonians, to the detriment of far more important East–West relations. Though Germany’s intelligence cooperation with Estonia was cool, its interest in what the spy agency there was cooking up with the British was keen. Simm declines to discuss this in detail, reverting only to his formulaic ‘I helped lots of people’. I can reveal, having heard it from multiple sources, that Germany apologised officially to Estonia in 2008, shortly after Simm’s arrest. If the BND had recruited and run an agent there in the late 1980s or early 1990s, when Russian organised crime was a serious problem for Germany, and the Estonian constitutional authorities were in no state to provide effective help, few would object. Continuing clandestine operations after 1992 was another matter. Estonia is not just a friendly country. It is one to which, since the Nazi–Soviet pact, Germany owes a historic debt. Most Germans would be horrified at the idea of running hostile intelligence operations against Israel. Those officials in charge of Simm (and presumably of other agents in the Baltics and Central Europe) may have neglected to consider Germany’s other historical baggage. It is easy to see why Berlin was interested in burgeoning Anglo-American defence cooperation with a new country in Germany’s Baltic backyard. But running a senior official there as a secret agent was no way to slake that curiosity.

Simm’s importance as a BND agent grew just as Germany’s relationship with Russia was intensifying. The friendship between Gerhard Schröder (federal chancellor from 1998 to 2005) and Mr Putin was notorious. It culminated in the German leader taking a retirement job as chairman of the board of a joint Russian–German gas pipeline, built on the Baltic seabed against the strenuous objections of the other littoral states, who saw it as a direct attack on their energy security. Some officials close to the case suggest that Simm was run on the direct instructions of the security coordination office in the Federal Chancellery under Mr Schröder, and against the judgement of the BND chiefs, whose attitudes to Russia were considerably more hawkish (and to Estonia, more friendly). That is hard to prove: everyone involved declines any kind of comment. All Simm will say is that he turned to the Germans as a ‘protection’ against the Russians. This suggests strongly that he was recruited by the BND after 1995, not before.

What is clear, however, is that Simm’s cooperation with Russia and Germany overlapped. That raises an interesting question. Did the SVR know that Simm was working for the BND? And did the BND know that he was working for the Russians? The former is more likely. The BND has long been something of a laughing stock among other secret services, because of the degree of Russian (and now Chinese) penetration. In Cold War Berlin in the 1980s, a senior intelligence officer from an English-speaking service told me derisively: ‘If we want Gorbachev to know something and take it seriously, we give it to the BND and tell them it’s top secret. It’ll be on his desk in the Kremlin the next morning.’ Little suggests that security has improved since then.

It is possible that Simm told the BND that he was under pressure from the Russians in the hope that they would rescue him were he exposed. At least one senior official close to the case says that Simm indeed played this card when he was arrested. The BND responded quickly by saying that Simm was a former agent, not a current one, and that the Estonians were welcome to try him for spying for Russia. At any rate, the Estonians have gone to great lengths to conceal evidence of Simm’s work for the BND. No questions to Simm on this subject were permitted during my face-to-face interviews, and he was also deeply reluctant to address the subject on the phone, or via intermediaries. ‘If I tell you that, I will be dead in my cell tomorrow,’ he said dramatically. In another interview he said elliptically, ‘I had to make sure that the pigs were fed but that the wolves did not go hungry.’ One reason for Estonia’s unwillingness to raise Simm’s BND connection was that it would have required another criminal trial. Another was the excellent relations that now exist between Estonia and Germany under Angela Merkel. The normally ultra-cautious Germans showed strong support in the crucial meetings that decided Estonia’s application to join the euro zone in 2009 and 2010. Some have suggested, plausibly, that this was a quid pro quo for Estonia’s willingness to hush up the unpleasant question of Simm’s work for the BND. The prime minister, Andrus Ansip, is fond of saying: ‘What is good for Germany is good for Estonia.’ But the result of the Simm case has been to dent trust – not only in Estonia – that Germany is an honest partner for its smaller neighbours in NATO and the EU.

The overlap raises a still more intriguing question: whether Russia knew that Simm was spying for the BND, and if so whether it tried to exploit this. It would certainly explain its remarkably unpleasant treatment of its once-prized agent in the final year of his service to them, which is only really consistent with a case officer who actively wants his source to be exposed. If the SVR did know – perhaps from Simm, perhaps from a source in Germany – that it was dealing with a double agent, then an elegant way of ending the affair would be to stage this denouement. Simm was of no further use to the SVR. Antonio himself needed to be recalled to Russia before he was arrested. Under interrogation, Simm would certainly mention his BND link, in the hope of invoking powerful outside help. Any outcome would then be good for Russia. Perhaps Estonia would hush the whole affair up, in which case it would spare the SVR’s blushes. It would certainly have a private or public spat with Germany, weakening NATO and underlining the isolation and fragility of the Baltic states’ security arrangements.

This is an elegant but not wholly convincing explanation of Russian sloppiness towards Simm. Anyone considering treachery naturally worries about how he will be treated. A reputation for callous carelessness does not help. Simm’s treatment damages the SVR brand. A better explanation is that Antonio himself was recruited by the Americans and helped set up Simm’s prosecution. This fits rather more of the facts. It would explain, for a start, the mysterious disappearance of Antonio following his clumsy and revealing phone call to Simm’s mobile. It is hardly likely that its spycatchers would succeed in nailing Simm but fail to gain the much bigger prize of a fully fledged Russian illegal. It is interesting to speculate when the double-dealing started: was Antonio already under Western control when he made his clumsy pitch to the Lithuanian? It would be nice to imagine that the Western intelligence services were using the Russian illegal for their own purposes, testing weaknesses in NATO members’ security and gaining a revealing picture of the SVR’s wish-list, sources and methods. Perhaps not only Simm but also other Russian agents run by Antonio have now been rounded up.

At any rate, the official story of simple SVR sloppiness looks incomplete. Retrospective analysis of intelligence operations is always skewed by their outcomes: the successful ones appear to have been run brilliantly; the failed ones look doomed from the start. But in all of intelligence history, it is hard to find an example of an illegal blown solely because of bad tradecraft. They normally trip up on one of two fronts. One is a spouse or lover who becomes suspicious of a pattern of activity that only he or she is in a position to notice. The other is penetration. But Antonio did not have a woman in his life. Rumours swirl around Tallinn and other cities about his whereabouts now, and the means used to recruit him. He was supposedly detained in Turkey around the time of Simm’s arrest, but has not been heard of since. One version is that the Western secret services planted child pornography on his computer, and told him that he would face a lengthy sentence in a Spanish jail unless he cooperated. Another account is that he was offered a large sum of money for his help, which he initially spurned. He returned to Moscow in a panic and alerted his controllers – only then to think better of his decision and slip out of Russia to the West where he then defected.

A final puzzle is the relationship between the Simm case and the American illegals such as Anna Chapman and Donald Heathfield. According to the Russian authorities, a senior SVR officer, Aleksandr Poteyev, defected to the United States in June 2010. In June 2011 a military court in Moscow sentenced him in absentia to a 25-year jail term on charges of treason and desertion. Aged 58 at the time of his trial, Mr Poteyev was a decorated intelligence veteran of the Soviet war in Afghanistan, who was then posted first to Washington, DC and then to New York in the early 1990s to service the illegals network. During that posting, he appears to have been spotted by the CIA as a potential recruit, with the initial approach being made via his daughter, who worked for an American academic exchange outfit in Moscow. A decisive psychological nudge – according to Russian news reports – came with a CIA-staged burglary at his flat.¹⁵ This supposedly underlined the weakness of the Russian state and the omnipotence of the Americans.

From 2000 Mr Poteyev worked as deputy director of the North America division of the S-Department (dealing with illegals). It is hard to imagine a more useful asset for the CIA, at least from a counter-espionage point of view. Mr Poteyev was able not only to give details of the identities of his agents in North America, but also to keep an eye on their missions, tasking and intelligence results.¹⁶ According to Russian news reports (which as officially sanctioned leaks must be taken with a Siberian salt mine’s worth of scepticism), Mr Poteyev was able to evade a lie detector test and also get his daughter and son outside Russia before he himself defected. He is said to have feigned illness, travelled to Belarus on a false passport provided by the Americans, and then to Kiev, where he was exfiltrated to Frankfurt. A text message to his wife read: ‘Mary, try to take this calmly: I am leaving not for a short time but for ever… I did not want this but I had to. I am starting a new life. I shall try to help the children.’ If true, the whole episode reflects sloppiness by the SVR’s once-fearsome internal counter-intelligence.

Mr Poteyev’s recruitment would have been the third blow to Russian espionage in North America in twenty years. The Mitrokhin archive, when analysed in the early 1990s, produced details of many illegals planted in the United States and Canada in the Soviet era. Almost all of them appeared to have become inactive when followed up by the FBI: they had settled into a quiet suburban routine, with the undemanding long-term tasks that would be needed only in time of war. (One illegal in Europe was provided with a carefully constructed false identity in order to get an unremarkable job at a car factory. His sole intelligence-gathering task was to inform Moscow of any sign of its switching to military production). The second blow came with the defection of Sergei Tretyakov, the deputy head of the SVR station based at the Russian mission to the United Nations. He was passing secrets to the United States from 1997 until his defection in 2000.¹⁷ His duties also included some support for illegals’ networks. Mr Tretyakov died, apparently of choking on a piece of meat, on 13 June 2010, on the eve of the spy scandal. Nobody has alleged foul play, although the coincidence is certainly striking. On top of that came the reported breach from Mr Poteyev.

Making sense of all this is tricky. The all-embracing conspiracy in which one side masterminds every twist and turn of a story is rarely a satisfactory explanation. History suggests that real answers to intelligence puzzles invariably include large doses of incompetence and misjudgement. Assuming that Antonio did indeed defect to America, Simm’s career in the Defence Ministry still remains mystifying. Why did he rise so quickly? Why did nobody note his KGB past? The truth is, I fear, that Simm had developed an unofficial relationship with Kapo, which was concerned about the growing Russian interest in Estonian defence, the scope for provocations and penetrations, and the weakness of the ministry in dealing with the threat. Soon after Simm’s arrival, Kapo picked up his sloppy behaviour. But instead of having him fired, it made him the agency’s unofficial eyes and ears, providing a stream of gossip, innuendo and other information. Kapo felt it had the weaknesses of the ministry under excellent scrutiny. And so they did – except the one that mattered. This theory is denied by all concerned, but I believe it to be true. As I shall argue in the conclusion, our complacency towards the mediocre is Russia’s deadliest weapon.