The Plot to Hack America: How Putin's Cyberspies and WikiLeaks Tried to Steal the 2016 Election

THE CENTRAL ORGANIZATIONAL HUB FOR THE Democratic Party is situated in a sand-colored modern building on Canal Street in Southeast Washington DC, just a few blocks away from the Capitol. In late April, 2016 the information technology division of the Democratic National Committee found problems in their system that indicated unauthorized access.

Upon discovery they called in CrowdStrike, an IT security company, to assess the damage. The hope was that it would be minor. Nuisance hackers attack with regularity, protesting various personal and political ideas and quack theories that usually involve the DNC and the Bilderbergs, the faking of the 9/11 attacks, or attempts to deny service in misguided attempts assist the opposition Republicans.

After CrowdStrike technicians implanted analytical software into the structure of the DNC’s servers, they soon discovered that two unknown entities had made an unauthorized penetration of the committee’s computers. The technicians immediately recognized that this was not a nuisance attack; it was a professional hit using professional tools and software. The CrowdStrike team started a series of analytical tests to discover the methods of entry and to outline the pathways that the hackers took into the server system. The tests would allow the cyber sleuths to determine where the hackers went, what they did while inside, and what data they may have taken. Another team checked the DNC’s server logs to see what the hackers had manipulated out of parameter. All of the parameters of the hack would take weeks to lay out in an official report, but it was almost immediately clear that this was not the work of amateur hackers.

Once inside, the two unauthorized users had started rooting around. One entity had implanted itself and had been monitoring the emails and chats of the Democratic staff for months, stealing files, emails, and voice messages—almost everything. The second entity, seemingly operating independently, had targeted two very specific files.

The treasure in political espionage is to know precisely what your enemy knows about you. Every intelligence agency seeks to find the details of the inner management of their opposition, but finding the file summary of what they actually know, what they don’t know and—equally important—what they know that they don’t know, is intelligence gold. For the political season of 2016, the most highly-prized information in the DNC’s servers would be the opposition files held by the Democratic Party about the seventeen Republican Party’s candidates.

The CrowdStrike damage control team determined that the penetration operation conducted by the unknown hackers had left the servers of the Democratic Party severely compromised. They had copied or taken materials of all kinds, and had infiltrated virtually everything of value to a political opponent: personal file folders, official chat threads, digital voicemails, and the email content of virtually everyone’s mailbox. The hackers also obtained the DNC’s donors lists, and it is likely that the donors’ credit card information was associated with these lists. One of the more fascinating aspects about this attack is that it was bold and brazen; many cyber security experts are a little surprised at how the hackers didn’t cover their tracks deeply, as if they wanted to be discovered. There was just enough cover to be deniable, but as one expert observed, it was a “big cyber F-you.” It was an electronic equivalent of a looting where the perpetrators throw everything around on the floor just to let you know they were there.

CrowdStrike quickly determined that the penetration into the servers started in the summer of 2015. Hand in hand with the successful penetration the next year, it would appear that the older attempt was an exploratory operation to determine the security settings on the server’s network. This probe would lay the groundwork for the determined and focused 2016 attack. However one factor was unshakable; the timeline of the 2016 hacks on the computers of the Democratic National Committee clearly indicated that the collection and dissemination was timed to benefit only the opposition Republican Party. Worse, if the hack was truly malicious, even relatively innocent information such as personal discussions, preferences, and the rivalry or relationships among co-workers could be twisted and injected into the national conversation in the months leading up to the election. This was not lost on the Chairperson of the DNC, Debbie Wasserman Schultz. She knew that scandal or not, the Republicans would use the hacked information to attack.

The Republican Party has shown an uncanny proclivity for taking an innocuous subject and by dint of repetition, inference, and outright false accusation make a seemingly innocent remark turn into years of acrimonious investigations. When Democratic staffers removed the letter “W” from a couple of Old Executive Office building computer keyboards, the Republicans turned it into a national campaign about how the White house itself was horribly vandalized by hordes of Democrats. When the staff at the White House travel office was routinely replaced upon the arrival of the freshly sworn-in President Bill Clinton, the scandal machine turned it into a witch hunt of national proportions that led to congressional investigations over abuse of power and personally targeted the First Lady. It’s been joked that had George Washington confessed to cutting down the cherry tree in the modern era, he would have been investigated for destruction of government property and abuse of authority, and promptly impeached.

However, this hack was unprecedented. The exposure of all of the internal discussions on the processes, procedures, strategy, beliefs, and thoughts of every staffer at the DNC from Debbie Wasserman Schultz down to the concerned citizen who calls and leaves a voice mail, was staggering. Any innocent comment could be turned into a political flamethrower. All discussions could be framed as conspiracies. The question at hand for the DNC became not who conducted the hack, but what would they do with the information.

Watergate 1.0

In 1972, President Richard Nixon, through his proxies in the White House called “The Plumbers” and in coordination with the Committee to Reelect the President (aka CREEP), sent five men into the offices of the Democratic National Committee in the offices at the luxurious Watergate hotel in Washington DC. The burglars had orders to install wiretaps, break into safes, and copy files to find out exactly what opposition research the Democrats had on Nixon in the months before the election. Although he won the presidential election, by August of 1973, the political scandal of covering up the crime led to Nixon being the first President to resign in disgrace.

The 2016 DNC hack conducted forty-four years later—almost to the day—was the exact same operation. However, this time there would be no security guard to detect the intrusion, and the burglars would not be caught wearing latex gloves and planting microphones. They would copy the information in a matter of seconds, their digital fingerprints would emerge long after the break-in, and discovery would occur well after the damage had been done to Hillary Clinton’s presidential campaign.

There were a myriad of suspects on the political stage from Trump supporters to Black Hat members of Anonymous, the shadowy hacker collective that sought to expose hidden secrets though public sun lighting. Though the DNC is a political machine that managed the Democratic Party and the campaigns of its members to office, it also operates as the framework to express the political aspirations of a huge proportion of the American electorate.

When President Barack Obama won re-election to the Presidency in 2012, he won over 65 million votes representing 51.1 percent of American voters. The management team for that electoral success was the DNC. They not only represent the candidates, but once the candidates are selected the DNC is the principle agency for the grooming, funding, and support to meet the goals of the party. Now, all of their internal secrets were stolen.

The general understanding at the time was that the DNC could contain the damage resulting from the hack, and the DNC claimed that nothing had been pilfered.¹

The general inner workings were relatively tame so long as they were not in the public domain. In June 2016, DNC Chairwoman Debbie Wasserman Schultz stated that,

After the April hack had been discovered, the analytical study of what was stolen was compiled. Crowdstrike and DNC officials figured out very quickly that the attack was broad and that the hackers had access for as long as ninety or more days where they entered and exited the servers and reviewed and took what they pleased. However, there was an early indicator of the intent of the intrusion.

If an advocate of the Republican Party, a citizen hacktivist, or a malicious “Black Hat” hacker anarchist had perpetrated the intrusion, it would have been a much sloppier operation. Additionally, the perpetrators would likely have taken or destroyed the dossiers of every Republican Party candidate in a cyber version of a bonfire. Hacktivists love the anarchy of letting systems administrators know that they have been violated. On the other hand “White Hat” hackers, internet security specialists who often win contracts by illegally entering systems usually leave notes so they can be contacted and help fix security flaws. They generally let the administrators know by leaving “I told you that you were vulnerable” messages in high-value files. All of this would have been old hat for the DNC computer administrators and CrowdStrike protection analysts, but the target of this second hacking was peculiar. It ignored everything and everyone except one set of files: The opposition research folders on New York City billionaire Donald J. Trump. This 2016 intrusion could arguably be called Watergate 2.0, but unlike the original Watergate, this time the materials would be used in a political process to damaging effect.

Trump’s Revenge: Erasing Obama’s Presidency

The White House Correspondents’ Dinner is an annual spring event hosted by the White House Correspondents’ Association. Sometimes referred to as “nerd prom,” the dinner brings journalists, politicians, and celebrities to the same room and is often criticized for fostering a cozy relationship between the media and the very people they are supposed to cover. The President usually delivers a humorous monologue that is then followed by a performance by a comedian. Donald Trump was a guest of The Washington Post at the 2011 White House Correspondents’ Dinner.

It was just a month before the dinner that Trump had become a leading voice in the so-called “birther movement,” raising the preposterous charge that President Barack Obama was not born in Hawaii as he claimed, but rather in Kenya. Trump publically and repeatedly called on President Obama to release his birth certificate. The New York Times wrote, “The more Mr. Trump questioned the legitimacy of Mr. Obama’s presidency, the better he performed in the early polls of the 2012 Republican field, springing from fifth place to a virtual tie for first.”³ Trump’s notoriety as a blustering TV showman using blunt, racially-tinged conspiracy theories was making him a rising star in conservative circles. These insults were not lost on the President, so Obama dedicated a notable portion of his 19-minute speech to making jabs at the New York businessman:

After Obama’s remarks, comedian Seth Meyers didn’t let Trump off the hook. Many journalists noted Trump did not seem amused throughout the performance, particularly at Obama’s and Meyers’ insults. Roxanne Roberts, who sat next to Trump at the dinner, wrote in The Washington Post that Trump “didn’t crack a smile” at Meyers’ jabs. Meyers joked, “Donald Trump has been saying he will run for president as a Republican—which is surprising, since I just assumed he was running as a joke.” He continued poking fun at Trump, as Roberts noted, “lobbing jokes like grenades.”⁵ Roberts wrote, “In retrospect, Trump broke the classic rule of political humor that says that the only response to a joke about you is to laugh harder than anyone else in the room. Whatever he was thinking, Trump looked unhappy and gave pundits a reason to pounce.”⁶ Trump only fueled the fire when he didn’t attend any after parties, and instead headed directly to his jet from the dinner.

The following day, Trump told Fox News that he “really understood what I was getting into” saying, “I didn’t know that I’d be virtually the sole focus. I guess when you’re leading in the polls that sort of thing tends to happen. But I was certainly in a certain way having a good time listening.”⁷

If he was listening, what he heard did not appear to please him the slightest. He attacked Meyers directly. “Seth Meyers has no talent,” Trump said in an interview with Michael Barbaro of The New York Times the day after the dinner. “He fell totally flat. In fact, I thought Seth’s delivery was so bad that he hurt himself.”⁸ He told Barbaro the evening was “like a roast of Donald Trump.” Still, Barbaro described him as “clearly reveling in the attention, if not the content.”⁹

In retrospect, the events of the 2011 White House Correspondents’ Dinner may have at least partially motivated Trump to run in 2016. The New York Times’ Maggie Haberman and Alexander Burns wrote, “That evening of public abasement, rather than sending Mr. Trump away, accelerated his ferocious efforts to gain stature within the political world. And it captured the degree to which Mr. Trump’s campaign is driven by a deep yearning sometimes obscured by his bluster and bragging: a desire to be taken seriously.”¹⁰

Clearly stung by the dinner jokes, it would be natural to see how Trump might relish revenge. Harnessing the power of the conservative poll numbers running for President in 2016 would give him the power of dismantling Obama’s legacy himself.

Trump Enters Politics

When Donald Trump announced his presidential run on June 16, 2015, he entered an unusually large field of eleven major Republican candidates seeking the White House. By the end of July, that field would expand to an unprecedented seventeen major Republican candidates, a hodgepodge that included nine current or former governors, senators, a retired neurosurgeon, and the former CEO of Hewlett Packard.^{11, 12}

Polls early on in the contest showed Trump with an immediate edge over most of the candidates, with a June 26–28, 2015 CNN/ORC national poll showing him polling at 12 percent among Republicans, second after former Florida governor Jeb Bush at 19 percent.¹³ By July 22–25, 2015, a CNN/ORC poll showed the New York businessman topping the polls at 19 percent, with Bush trailing at 15 percent.¹⁴ Always outlandish, his brash style and ability to “tell it like it is” attracted crowds of admirers. He was an instant success among the conservative fringe and had the ability to bring that fringe into the mainstream.

The hallmark of his campaign was using hyperbole and personal insults with just a touch of Orwellian double speak. For example, he would make contradictory statements, on one hand praising veterans but insulting John McCain for being shot down and spending years as a prisoner of war in Vietnam. On July 18, 2015 Trump threw out an offhand remark about McCain. “He’s not a war hero,” Trump said. “He was a war hero because he was captured. I like people who weren’t captured.”¹⁵ When pressured he would claim he never said any such thing and allow the next outrageous statement to wash over the last one.

Despite his high poll numbers, most of the media and electorate did not initially take his campaign seriously. The Huffington Post went as far as to announce in July 2015 it would run all Trump-related stories in the Entertainment section. “Our reason is simple: Trump’s campaign is a sideshow,” the announcement read. “We won’t take the bait. If you are interested in what The Donald has to say, you’ll find it next to our stories on the Kardashians and The Bachelorette.”¹⁶

Even the renowned statistician Nate Silver—founder of the polling analysis website FiveThirtyEight who had a near-perfect track record of correctly predicting the winners of the presidential contests in each of the fifty states during the 2008 and 2012 elections—couldn’t fathom Trump’s rise.¹⁷ In November of 2015, with the Republican field narrowed down to twelve candidates, Trump topped the polls. Silver put Trump’s chances of winning the Republican nomination below 20 percent. Silver wrote, “For my money, that adds up to Trump’s chances being higher than 0 but (considerably) less than 20 percent.”¹⁸

As Christmas approached it looked increasingly probable that Trump would not lose his lead. It was at this time that Trump received a peculiar endorsement. Out of the blue, Vladimir Putin, President of the Russian Federation, made a series of comments about the U.S. election that seemed to endorse Trump. Putin said of Trump in a press conference “He is a bright and talented person without any doubt. He is the absolute leader of the presidential race…”¹⁹ Putin’s endorsement was a surprise to most but not to those who had been noticing the penchant Trump had towards the Russian autocrat and his glowing admiration of other dictators such as Kim Il-Sung and Muammar Gaddafi.

Trump continued to top each poll as rivals began to fall. Former Florida Gov. Jeb Bush—once considered to be a shoo-in for the GOP nomination—continued to slip before dropping out after his February loss in the South Carolina primary. In the months leading up to Trump’s nomination, former neurosurgeon Ben Carson, Texas Senator Ted Cruz, Florida Senator Marco Rubio, and former Hewlett-Packard CEO Carly Fiorina each at different times found themselves in second place to Trump, but none could catch up to his lead, according to various CNN/ORC polls.²⁰

By spring the race to become the Republican presidential nominee had narrowed down to three candidates. On May 3, Trump became the presumptive GOP nominee when Senator Ted Cruz dropped out of the race after losing the Indiana primary. Ohio Governor John Kasich suspended his campaign the next day.²¹ The field was vanquished and against all expectations, Donald Trump officially became the party’s nominee at the Republican National Convention in June.²²

Between August 2015 and March 2016, the Republicans held a total of twelve presidential primary debates. The Democrats held nine.²³ Trump certainly made splashes in the first Republican primary debate in August 2015, receiving both cheers and boos from the crowd at the Quicken Loans arena in Cleveland, Ohio.

When a moderator asked the ten Republican candidates on stage if anyone was unwilling to pledge their support to the eventual nominee, Trump was the only candidate to raise his hand. Receiving boos from the audience, Trump said, “I can totally make the pledge if I’m the nominee. I will pledge I will not run as an independent. I am discussing it with everybody. But I’m talking about a lot of leverage. We want to win and we will win. But I want to win as the Republican. I want to run as the Republican nominee.”²⁴

Trump also gained a reputation for his bluntness and constant criticism of political correctness. “I think the big problem this country has—is being politically correct,” he said during the Fox debate, receiving cheers from the crowd and highlighting a theme he would exploit throughout his campaign. “And I don’t frankly have time for total political correctness. And to be honest with you, this country doesn’t have time either.”²⁵

Trump electrified a segment of the conservative electorate. He fired them up at unprecedented levels and relished the electricity in the air when the rallies had unusually high number of protesters and descended into violent altercations. Trump was repeatedly criticized for encouraging violence. Kevin Cirilli wrote for Bloomberg:

The violence wasn’t limited to those in the crowd. His campaign staff mimicked the aggressive stance of the candidate. Trump’s campaign manager Corey Lewandowski was accused of forcibly grabbing conservative Breitbart News reporter Michelle Fields hard enough to leave a bruise at a campaign rally in Florida. Lewandowski was charged with misdemeanor battery, charges that were ultimately dropped. But it was Trump’s response to the incident that worried some. Vox explains:

The entire demeanor of the campaign was called into question. Trump chief strategist, Paul Manafort, addressed these concerns at an April closed-door meeting of the Republican National Committee. Ashley Parker writes in The New York Times:

Trump himself has claimed that even his wife, Melania, and daughter, Ivanka, have called on him to act more presidential. Two days after Manafort addressed the RNC, Trump addressed the calls himself at a campaign rally in Connecticut, saying he wasn’t about to start “toning it down.” Parker writes:

Worse than his mouth was his fingers when connected to an Android smartphone with access to Twitter. In 140 characters he managed to derail his candidacy with insulting, racy, or inappropriate comments including those retweeting neo-Nazi and White Supremacy comments. The former host of The Apprentice often takes to Twitter to blast those who speak critically of him. The New York Times even kept a running list of the “People, Places and Things Donald Trump Has Insulted on Twitter.”³⁰

The Democratic Simmer

Compared to the unusually large number of candidates competing for the GOP nomination, a number that remained in the double digits through the Iowa caucuses, the Democratic side pitted two main candidates against one another from early on: Former Secretary of State, U.S. Senator and First Lady Hillary Clinton and Vermont Senator Bernie Sanders.

Initial CNN/ORC polls showed Clinton with a big lead over Sanders, with a poll conducted June 26–28, 2015 showing Clinton polling at 58 percent to Sanders’s 15 percent. Other would-be candidates Jim Webb, Lincoln Chafee, and former Maryland Governor Martin O’Malley never polled higher than 3 percent, according to an analysis of CNN/ORC polls.³¹ O’Malley suspended his campaign after the February 1, 2016 Iowa caucus.

For a self-proclaimed democratic socialist from Vermont, Sanders had a decent showing in the 2016 race for nomination. A March 17–20 poll showed Sanders reaching a high of 44 percent support to Clinton’s 51 percent.³² Distrustful of Clinton and the Democratic Party machine, Sanders’s followers were ardent and deeply believed that the power structure of the Democratic Party could be overturned in a new liberal progressive era. Accusations of vote rigging, favoritism, and delegate manipulation permeated the campaign. By the time Clinton secured the nomination a great deal of mistrust between the Clinton and Sanders supporters had set in. Clinton supporters saw Sanders’s campaigners as youthful, naïve, and ready to believe anything they read on the internet. Sanders’s supporters saw the Clinton machine in terms that Trump and the Republicans could appreciate: For over twenty-five years the Republicans had fostered an image of Clinton as a corrupt, dishonest, and manipulative liar who was ambitious at all costs, despite decades of investigations by Republican Congresses that had revealed no evidence of corruption or complicity in criminality.

The Benghazi Gambit and Email Questions

Sanders took a first shot at Clinton with his criticism of her emails related to the Benghazi scandal. In November 2015, after rejecting the scope of the Republican-led controversy, Sanders suddenly about faced, contending that any emails related to the subject were fair game.

A terrorist attack on the U.S. mission compound in Benghazi, Libya on September 11, 2012 went from being a regrettable incident leading to the deaths of four Americans to a full-blown Republican-manufactured conspiracy theory positing that President Obama and Hillary Clinton allowed Ambassador J. Christopher Stevens and his staff to die by issuing a “stand-down order.” Republicans attacked Clinton relentlessly for her handling of the Benghazi attacks as Secretary of State. Critics charged the administration didn’t listen to intelligence warnings ahead of the attack and subsequently covered up their actions. Nine separate congressional bodies investigated, and as Vox reported, “Each has identified problems with the way the incident was handled, but none have uncovered real evidence of an administration cover-up or failure to properly respond to the attacks.”³³ In October 2015, Clinton testified before the House Select Committee on Benghazi for over eleven hours. David Herszenhorn of The New York Times wrote, “The hearing was widely perceived to have backfired on Republicans, as she answered their questions and coolly deflected their attacks.”³⁴ The Committee released its final report as the primary campaigns were wrapping up in June 2016. The Times reported “no new evidence of culpability or wrongdoing by Hillary Clinton.”³⁵ Still, hours after the release of the report, Trump tweeted, “Benghazi is just another Hillary Clinton failure. It just never seems to work the way it’s supposed to with Clinton.”³⁶

In the end nothing helped the Sanders Campaign. Clinton had won more than three million more votes and by June, however, Clinton had won enough delegates to secure the nomination, also beating Sanders in the superdelegate count.³⁷ On July 12, with less than two weeks until the Democratic National Convention, Sanders endorsed Hillary Clinton. In a post published the day of his endorsement, Sanders wrote he could not “in good conscience” allow Donald Trump to be elected President. “Today, I endorsed Hillary Clinton to be our next President. I know that some of you will be disappointed with that decision,” he wrote. “But I believe that, at this moment, our country, our values, and our common vision for a transformed America, are best served by the defeat of Donald Trump and the election of Hillary Clinton.”³⁸

A hallmark of the 2016 campaign was the effort to damage Hillary Clinton with information related to a private email server located in her home while she was Secretary of State, which first surfaced in March 2015. Republicans, as well as some in the Bernie Sanders campaign, desperately wanted Clinton to be found criminally liable for the usage of private emails for official business. Despite Sanders saying he was “sick and tired” of hearing about the emails, his campaign manager Jeff Weaver bluntly told Fox news that it would be hard for Clinton to keep running for election if she were “under indictment.”³⁹

This level of talk got Sander’s supporters as frothed up as Trump supporters and the wait was on for the FBI investigation to conclude and rule against her so Sanders could walk away with the nomination. The email controversy was now the core of the Republican strategy; they theorized that if Clinton was indicted then her campaign and political career would be over and that Trump could easily insult Sanders to victory.

However, this was not to be. The FBI did conclude its investigation and determined that Secretary Clinton did not intentionally commit any crimes. There would be no indictment. The FBI determined that 110 of the 30,000 emails Clinton originally turned over contained information that was classified at the time she received them, but most had classification markers removed. Clinton had not deliberately misled anyone nor had she lied to the FBI. FBI Director James Comey called her actions “extremely careless,” although the agency recommended no charges be filed against the former Secretary of State.⁴⁰

Seemingly nothing could derail the Clinton nomination. The Democratic Convention in Philadelphia was fast approaching and the last chance for Clinton’s detractors to take down her campaign by the use of the emails had seemingly evaporated.