SEAN CHERCOVER

This former P.I. has the experience to infuse his writing with a heavy dose of authenticity. His realistic portrayals of both cops and the down-and-outers of the world have garnered Sean high praise and well-deserved awards. His first novel, Big City, Bad Blood, even gets praised on the FBI’s Web site for its accurate depiction of law enforcement. His writing has been compared to Steve Hamilton, Lawrence Block and Dennis Lehane, but as his readers know, Sean has a powerful voice all his own.

Sean’s intense love of scuba diving is sometimes reflected in his fiction, so it’s fitting that his experience in the waters of the Caribbean can be felt in “A Calculated Risk.” Tom Bailey, the main character, uses his deep passion and understanding of the water and boats to make a living. He’s brushed up against the wrong side of the law many times before but this job takes him firmly over the edge. The real question is-will he be able to come back?

A CALCULATED RISK

Tom Bailey turned the wheel over to starboard and guided his forty-two-foot power catamaran, Zombie Jamboree, just inside the coral reef, relying on the lower helm’s depth finder and night-vision monitor. He stole a glance at the luminous hands of his Submariner: forty minutes until dawn. Perfect timing.

The man who called himself Diego said, “How’s our timing?”

“Perfect.”

“Better be.”

A threat? Or just a common expression. The man’s tone was even, carried no particular menace. It was hard to tell. And because they were running dark, Bailey couldn’t read anything in the man’s face.

But he was tempted to say, Or what?

He said, “Dude, you came to me, I didn’t come to you.” He checked their GPS coordinates, cut the engines. The tide would take them in quiet from here. “Twelve minutes and we’ll be right on Labadee Beach.”

Labadee was a private beach within a walled compound on the north shore of Haiti. Royal Caribbean Cruise Lines owned the beach and the compound. The whole place would be empty until the next cruise ship arrived on Thursday. This was Tuesday. The Zombie Jamboree drifted in on the tide and the men didn’t speak until they arrived at Labadee.

Right on time.

“Can we get close enough?”

“She’s a cat, she draws three feet,” said Bailey.

About thirty feet from shore, Bailey said, “You jump in now, you’re about up to your nipples. Tide’s behind you. You can wade in from here.” They walked out to the aft deck, Bailey carrying a flashlight with a red lens to deaden the light, the other man carrying a black Pelican case. About the size and shape of a thick briefcase, but made of injection-molded plastic, with O-rings and strong latches and a one-way purge valve.

Watertight.

The man who called himself Diego stopped on the swim step, looked up at Bailey. He said, “You remember what I told you.”

Bailey smiled. “Don’t worry about me.”

Even in the dim light, the man’s eyes shone with contempt. “I have to worry about you,” he said. “You are the one part of the plan I can’t control. I know I won’t fuck up. I plan everything, down to the minute, and then I execute with precision. I leave nothing to chance. The only chance of failure is if you fuck up.”

“Bad logic,” said Bailey. “If I fuck up, then you fucked up by hiring me, dude.” Bailey didn’t usually say dude this often. But he could tell that it bothered his client, and he didn’t like his client.

The man looked to the deserted shore, back at Bailey, and launched into it again. For the seventh time. “You head straight for Dominican waters. You stay there. Go fishing. Go diving. Work on your tan. Whatever. You don’t go ashore. You don’t get drunk. You don’t smoke grass. You put down anchor at the end of the day, like you’re settling in for the night. You go dark. You stay dark. You return here at eleven-thirty tonight. Right here. Yes?”

“Yes, Diego.” Bailey waved the flashlight toward shore. “And I signal with three flashes, at three-minute intervals.”

“All right.” The man let go of the railing, sunk until his feet hit the sandy bottom. He was about up to his nipples. He started walking toward shore, the black Pelican case floating out in front of him on the calm water, its handle in his left hand.

Starlight glittered silver off the black water, creating a gossamer wake behind the man as he waded in. There was the gentle hiss of the tide kissing the sand, and the ever-present tree-frog music, floating on the sweet island breeze. And that was all.

Not a soul on the beach to witness the arrival of the man who called himself Diego.


Bailey jabbed at the purge valve of his regulator, then stuck the regulator in his mouth. He put his right hand over his face, applying pressure to both mask and regulator. Left hand, holding the spear gun, pressed against his chest. Rolled back, plunged into the Caribbean Sea.

Like falling into a warm bath. Beneath the surface was where he felt truly at home. At peace. He needed the time down here, and tried to get a dive in every day.

He kicked his fins, got some depth, pinched his nose through the silicone mask and cleared his ears, kicked again in the direction of the anchor line.

The top of the coral reef was forty-two feet from the surface, and Bailey added a little air to his BC as he arrived. He floated along the top of the reef, pulled the rubber tubing back to ready his spear gun.

Tried to concentrate.

But his mind was busy, replaying the initial meeting with his client.

“Your monkey cannot come along,” said the man, and gestured to the vervet monkey that sat on the starboard bench devouring a mango. The monkey mistook the man’s gesture, let out a piercing shriek and scooted back a foot, clutching the mangled mango to her chest.

“Relax, I don’t want your fucking mango,” said the man. Then, to Bailey, “See? He’s loud.”

The wake of a passing yacht caused the Zombie Jamboree to rock ever so slightly, and the man overcompensated with his leg muscles like a subway virgin, almost stumbled, but corrected in time. The man was clearly not possessed of sea legs, and Bailey didn’t relish the idea of a seasick passenger. He decided to charge extra.

Bailey took his feet off the gunwale and planted them on the deck, stubbed out the joint he was smoking.

“She.”

“What?”

“She,” Bailey repeated. “She’s loud. Her name is Miss Judy.” He took a swig of Dos Equis, then rubbed the cold bottle against his bare chest. “Anyway, she doesn’t live aboard. She’s just a friend, she’s not my monkey. She’s not anybody’s monkey.” He hit the man with a goofy smile.

The man waved Bailey’s words away impatiently. “I don’t give a shit. Boy monkey, girl monkey. Your monkey, not your monkey. The monkey is not to come with us on this trip. Understand?”

“Sure. No monkey.”

Bailey didn’t like this man, but then again, he didn’t like a lot of his clients. Liking your clients was not part of the people-smuggling business.

Most of Bailey’s clients were rich Americans sneaking into the Bahamas to engage in some extramarital recreation, or to drop some cash at the local casinos. The smarter ones came to stash money in offshore accounts. Bailey didn’t smuggle things, just people. There was too much risk when you started moving unknown cargo across international borders. You might get boarded and find yourself holding fifty keys of coke. Or guns. Or anything. It wasn’t worth it if you got caught, and even if you didn’t, there were moral considerations. Where were the guns going? Would they be used to liberate people, or enslave them? Were the drugs going to middle-class suburbanites, or would they contribute to the rot of the inner cities? So Bailey saved himself the headache. People were easy. Easy to move, easy to hide. And people-smuggling had always seemed morally uncomplicated.

Free people moving about freely. The idea held great philosophical appeal. At least, it used to. Things changed after 9/11, but Bailey was a good judge of people and he knew he’d never smuggled a terrorist. Not yet. Lately, he had started to consider the merits of retirement. Of going legit.

He could continue to run the Zombie Jamboree as a fishing charter, simply knock off the undeclared, cash-only side business. But if he were going legit, it wouldn’t be as a fishing charter. Too much stink, and all his time spent on the surface, and too many asshole customers who blame the captain when the fish don’t bite.

No, the plan for going legit went like this: move to an island where he wasn’t known-an island with a good economy and stable political climate. Barbados was perfect. Buy a small dive shop there, and hire a couple of young guys to help run the place. Maybe even move ashore and charter the cat for pleasure cruising. Or hire a local captain to babysit the fishing tourists.

That was the plan. But it was a plan with a significant price tag, especially on an island like Barbados. If he stayed with the people-smuggling sideline, he might make the nut in a couple years. But if he went legit as a fishing charter, what with the cost of fuel these days, it could take another decade.

So a couple more years of people-smuggling, and out. He’d still be a few years on the right side of forty when he reinvented himself yet again, this time as a law-abiding dive-shop operator. He might even meet a nice woman, fall in love…have a kid.

Or maybe he was kidding himself. But what the hell. He’d come a long way on this ongoing journey of personal transformation; might as well buy in to the whole dream. Stranger things have happened.

The man who called himself Diego was no terrorist, but neither was he simply a playboy looking for a good time or a tax dodge. Whatever he was, he was a hard guy. Dangerous. Not weight-lifter hard-those body-proud posers were only dangerous to themselves. Like Bailey, this guy had a lean and flexible musculature. His hardness was a mental hardness. Hence, dangerous.

Whatever this guy was, he was a bad dude. He knew it, and he knew that you knew it, and he never made any effort to convince you of it. That’s the way it is with truly dangerous men. They never try to convince anybody. They just are. If you’re an even halfway bad dude, you’ll recognize it. If you don’t, you’re not worth worrying about.

Bailey recognized it. He’d been a bad dude himself, in a former life. But that was before the first reinvention. These days he was known, to those who thought they knew him, as a friendly expat American who liked rum and reefer, diving and women, in approximately that order.

Among the Caribbean ’s expat, live-aboard set, there were two distinct groups. There were those, like Bailey, who never talked about their former lives, and there were those who never shut the hell up about their former lives. All you had to do is pull up a stool next to them at the beach bar and you’d hear all about it, in excruciating detail.

Dot-com millionaires who struck gold with an IPO and then dumped out just ahead of the bust; stock-market day-traders who’d had the discipline to quit while they were ahead; software developers; venture capitalists; real estate speculators; doctors and dentists who’d diligently saved their money and retired while still young enough to live the rest of their lives chasing after Jimmy Buffett’s bliss. The stories were all different, and all the same.

And of course there were the trust-fund babies. Their former lives consisted mostly of homogenous boarding schools and ski trips in the Alps and absent parents and kindly nannies. Bailey preferred the second-generation trust-fund babies; they seemed to have accepted their lot with a little more grace than their furiously idle parents.

Bailey’s group-those who didn’t talk about their former lives-consisted of retired arms dealers, drug runners, mercenaries, white-collar embezzlers and blue-collar thugs. A growing number of Russian “businessmen.” Also scattered around the Caribbean were former civil servants, mostly of the U.S. and U.K., some of France, and a few Israelis. Civil servants, true, but not the kind that ever saw the inside of a cubicle. Bailey had worked for Uncle Sam, in his former life.

The man who called himself Diego didn’t seem to fit any of these categories. He used the name Diego and spoke with a slight accent, but Bailey guessed that the accent was no more authentic than the name. He lacked the olive complexion, and while he had a good tan, it looked like it had been recently acquired in a salon. Bailey guessed the man for an American, but he couldn’t be positive.

Bailey’s initial dislike of the man only intensified while they talked. Although the man made no effort to act tough, ego asserted itself in a pronounced attitude of superiority. An attitude that says, I’m smarter than you and everyone else on this island, and I resent having to deal with men of lesser competence.

Still, there was no concrete reason to turn the man down. The gig was easy enough-pick the guy up at the Flying Fish Marina in Clarence Town, get him to Haiti, drop him off before sunrise, pick him up the same night, deliver him back to the marina the next day. The first pickup and final drop-off would happen in full view, and Bailey would have the boat set up like a regular fishing charter. Fighting chair in place, rods prominently displayed.

And the money was good. Ten thousand American dollars, plus fuel expenses. Cash. Always in cash.


Bailey returned to Labadee Beach at exactly eleven-thirty that night. He cut the throttle down to idle and scanned the shoreline through night-vision binoculars.

Nothing. He grabbed the big flashlight with the red lens, pointed it toward land, flicked the switch on and off three times. Glanced at his watch.

Three minutes later, he did it again. Still nothing.

Another three minutes, and then the flashlight dance again.

Where the hell was this guy?

After the fourth flashlight signal went unanswered, Bailey moved to the aft deck’s portside throttle controls and eased the cat closer to shore. He checked his watch again. Fifteen minutes. Something was very wrong.

I plan everything, down to the minute, and then I execute with precision. I leave nothing to chance.

And now the guy was late.

Bailey reached for the flashlight again, but before he hit the switch, there was a rustling of bushes at the top of the beach. The man who called himself Diego burst into view, ran down the beach and splashed into the water, the Pelican case in his left hand.

Bailey swung the boat around as the man waded out in a jog. He cut the throttle and moved to the swim step, keeping his eye on shore.

The beach was empty. Nobody giving chase.

The man clambered aboard. There was blood on the front of his shirt. A lot of blood.

“I’ll get the first-aid kit.”

“Stop.”

Bailey stopped, turned back. He looked the man over. No evidence of injury.

The man stared him down, said, “I had a nosebleed.”

“Right.”

“Just get us out of here, fast.”

“Fast or quiet,” said Bailey. “You can’t have both.”

“Fast.”

“You got it.” Bailey climbed up the ladder to the flybridge helm. “Hang on.” He jammed the throttles forward and the twin diesels roared up from idle. His blood-splattered passenger grabbed the ladder for support, but stayed down on the aft deck.

As they came around the reef, automatic weapons fire rang out from shore.

Pap-pap-pap-pap-pap-pap.

The man who called himself Diego flattened against the deck, but the gunfire sounded more like protest than attack, and it died rapidly. At this distance, with only dim starlight and no moon, with the boat running dark at thirty knots, the men on shore must’ve known they couldn’t hit anything. They’d be aiming at the sound of the engines and their bullets would be well off the stern. Still, Bailey felt adrenaline leak into his bloodstream, and blew out a long breath.

Haiti had a meager Coast Guard and Bailey didn’t think they’d be able to scramble a boat out in time, but he stayed up on the flybridge where he could spot any unwelcome company, just in case.

No boat appeared.

Outside the protection of the reef, the sea rose up and the swells grew to about seven feet. No challenge to the stability of the cat, but Bailey wondered if an unexpected storm was in their future. He’d checked the marine forecast earlier in the day, but conditions change quickly in these parts.

He switched on the radio. No storm on the way. Small consolation.

No moon. I leave nothing to chance. Damn. Bailey had noticed that it would be a moonless night when he’d checked the tide calendar. It should’ve raised a red flag, but he’d been too busy thinking about the ten thousand dollars. Too busy chasing his dream.

And now everything had gone to dog shit.

Bailey told himself to take it easy: cut out the self-flagellation and focus on the present situation. Yes, his client was wearing someone else’s blood, and yes, there’d been men with automatic weapons on the beach. But automatic weapons were relatively easy to come by in Haiti; the men on the beach could’ve been gangsters as easy as cops.

And then the radio rendered Bailey’s rationalizations impotent.

The Caribbean News Agency was reporting that Dominic Martel-the leader of Haiti ’s pro-democracy movement-had been shot to death that evening as he dined with his family in a restaurant in the town of Cap Haitien. Cap Haitien was only six miles southeast of Labadee Beach.

Shit. Bailey felt his stomach turn over. His client was an assassin.

Still no boat appeared, and he realized that there would be none. They’d gotten away clean. But now he had bigger things to worry about. Now he had to worry about his client. It was time to start being active, instead of reactive. Time to put the old skills to work.

There was no boat giving chase, but down on the aft deck, the man who called himself Diego could not see over the swells. Bailey set the autopilot, grabbed the flashlight and moved to the ladder, as if in a hurry.

“We got company,” he called down to the man. “Get inside.” He came down the ladder at speed and ushered his client into the pilothouse. The man didn’t argue.

Bailey opened a trapdoor in the cabin floor and climbed down a steep set of metal stairs into the port hull, just ahead of the engine room. It was hot and loud down there. He flipped a switch and fluorescent lights flickered to life in the ceiling.

“Come on, come on,” he said, waving at the man. He pressed on a false wall and it opened, revealing a small padded closet just large enough for one person. There was a built-in seat, also padded.

The man came down the stairs, clutching his case. He looked dubiously at the custom-built people-hider.

Bailey said, “It’s safe. It has its own ventilation. If we get boarded, they won’t find you.”

The man stepped inside, but he didn’t look happy about it.

Bailey pushed the false wall back into place. He climbed up the stairs, got a water bottle and a box of extrastrength Gravol from the galley, returned and pressed on the wall.

“Here,” he said, and handed the bottle to the man. He held the box of Gravol up for the man to see, then popped a couple of pills free of their blister pack. “Take these.” The man did not reach for them. “Listen,” Bailey said, “I’m gonna have to cut across the swells to lose these guys and it’s gonna get rough down here. You don’t take these, you’re gonna be puking all over yourself in about ten minutes. I can’t afford to have you choking on your vomit while I’m up top.”

The man swallowed the pills. Bailey shut the secret door.


At the lower helm station, Bailey shut off the autopilot and switched on the running lights. He turned the wheel and pointed the boat so that the swells hit sideways instead of head-on. The boat rocked side to side.

Then he reached forward and flipped a toggle switch, shutting off the ventilation to the people-hider.

He thought things through. The man who called himself Diego had taken a brief nap after Bailey had picked him up at the marina, but had not slept on the overnight journey from Long Island to Haiti, and Bailey doubted that sleep had been on his agenda during his time ashore. So he’d been awake at least thirty hours.

Shutting off the ventilation wouldn’t kill the man, but the oxygen level in the people-hider would deplete. Between that and the extrastrength Gravol, Bailey figured the man would be unconscious within the hour.


Bailey pressed on the secret door and eased it open. He was greeted by a beautiful sound. Snoring. The man who called himself Diego was asleep, reclined on the seat, his head resting against the padded wall. The Pelican case had slipped from his grasp and lay on the floor.

Bailey took the case, and gently closed the door.

Up in the lounge, Bailey flipped the latches and opened the case. He withdrew a map that showed a section of Haiti ’s north shore, from Labadee to the town of Cap Haitien. Beneath the map was a semiautomatic pistol. He lifted the pistol from the case, smelled it. Cordite. He put the recently fired pistol aside. There was money in the case. American money, about $30,000. Bailey fished around under the cash, found a passport. A U.S. passport. He took it out of the case and opened it.

His blood ran cold. Staring back at him was the standard passport photo of the man who called himself Diego. But the name on the passport was Tom Bailey.

I leave nothing to chance. So the man who called himself Diego wasn’t done killing.

Or thought he wasn’t. Bailey could take care of this threat without breaking a sweat. The man was asleep and Bailey had his gun. Easiest thing in the world, to walk downstairs and put a bullet in the man’s head with his own gun. End of threat. He could weigh down the body with an anchor and some line. Dump the body at sea, along with the gun. Done. Finished. Pretend it never happened.

But then Bailey thought about it from the other man’s perspective. A change of identity would mean relocating. It was an expensive proposition. It would mean a significant sum of money waiting for him in his new destination. Had to. But there was nothing else in the case to say where.

And that led Bailey on a new train of thought. Was this a crazy idea? A reckless bet? No, he decided. It was time to go legit-now-and this could set him on his new path. The man had an ego problem; he would play on that.

This was a calculated risk.

He would have to put the case back the way he found it-passport under the money, gun on top and the map covering the gun. Then return the case to the people-hider with the man and switch the ventilation back on.


Sunrise was breaking over a calm sea when the man emerged from below. The case was in his left hand. The butt of the pistol peeked out from his waistband.

“Good morning,” said Bailey. Cheerful.

“Where the hell are we?”

“Almost home. We made it.” Bailey gestured out the windows, to a speck of land on the horizon.

“That’s Long Island?”

“Yup. I’ll have you back on dry land in half an hour.”

“You got an extra shirt I can have?”

“No problem.” Bailey got a T-shirt from the stateroom in the starboard hull. When he returned, the man was pointing the gun at him. He tried to look surprised. “Take it easy, Diego,” he said. “If you don’t like the shirt, I’ll get you another one.”

“That’s actually very funny,” the man said. He was no longer affecting an accent. He gestured with the barrel of his gun to the aft deck. “Outside.”

Bailey put his hands up, even though the man hadn’t asked him to do so. He walked out to the aft deck, sat down hard on the portside bench, braced his hands on his knees and shook his head.

“Diego, I delivered my end of the bargain. You don’t have to do this. It’s not the smart play.”

“Actually, it is.” The man kept the pistol aimed at Bailey’s chest.

“I’m an accessory, before and after the fact-you know I won’t talk.”

“No, you won’t.”

“Killing me is only going to raise questions. I turn up dead, it’ll only bring more heat. You’re making a stupid move, here. Really stupid.”

The man smiled. A cruel smile. “But you’re not going to turn up dead. You’re just making a move.”

Bailey shook his head like he didn’t understand, and leaned back with his hands planted on the bench behind him. “I don’t understand. Where am I moving?”

“ Grand Cayman. It’s lovely there.”

“They’ve got private banking in Cayman.”

The man’s smile broadened. “I know.”

“Please, you really don’t have to do this.”

“No, I really do have to do this.”

“I’m telling you. Don’t be stupid.”

The man pulled the trigger.

Click.

The man snorted derisively. “Clever,” he said. He dropped the pistol on the deck and reached behind his back and came up with a throwing knife, as Bailey slid his hand under the bench cushion and came up with the preloaded spear gun he’d stashed there a couple hours earlier.

Both men froze.

“Mexican standoff,” said the man who called himself Diego.

“Not really,” said Bailey. “You may be good, but no arm can match the velocity of this thing. You’ll lose.” He locked eyes with the man, but instructed his peripheral vision to watch for any twitch in the man’s knife hand, poised to throw.

“What do you propose?”

“I’ll give you a choice. If you really think you can beat me, fire away. Or, you can take a swim.”

“You’re kidding.”

“I don’t think so.”

“I’ll never make it to shore.”

“No, you won’t. You’ll tread water for a while, then you’ll get tired and drown. You could get lucky, a boat may come along and pick you up. But that’s unlikely. You have a choice to make. Either way, it’s a calculated risk.”

The man thought for a second, nodded to himself.

The knife hand moved forward. Bailey pulled the trigger. The knife clattered to the deck at Bailey’s feet.

The man groped for the metal spear sticking out of his chest. He made a horrible gurgling sound, staggered backward. His arms flailed in the air as he toppled over the gunwale and into the Caribbean Sea.

Bailey crossed over to where the man who called himself Diego had stood, picked up the gun and tossed it overboard. He stuck his hand in his pocket, pulled out the bullets and dropped them into the sea.

Then he went inside and poured himself a long drink of rum.

Cayman. That’s where he’d find the money. It would be waiting for him in a bank account in his own name. He plotted a course for Grand Cayman and sipped his drink.

A calculated risk. And it had paid off.

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