There’s a story Tony Carleo likes to tell about a visit he made to Las Vegas over a decade ago, when he was in his early twenties.

“I was sitting in a casino,” he says, “and there was a crowd starting to gather around a craps table, people two or three deep because everyone wanted to see.”

A man was betting on hard eight, that the dice would land showing exactly four and four before he threw a seven or another combination that added up to eight. It was a long-shot bet, but the man hit it, then hit it again, his $5 turning into 50 then 500. Each time he let it ride. Carleo elbowed his way through the crowd to get closer to the action. On and on the man rolled, somehow avoiding crapping out – he hit hard eight again and then once more. The crowd of people exploded. To hit hard eight once was improbable, to hit it four times in row nearly impossible. The dealer slid forward the man’s winnings, a short tower of brightly colored chips worth $50,000 coming to rest where once there had been a single $5 chip.

For Carleo, the tale is proof of a belief that has always lived inside of him – as long as you have the balls to open yourself up wide to fate, there’s no telling what might come your way.

“If he could do it, I could do it,” Carleo says. “It could happen to me.”

Years later, in December of 2010, Carleo arrived at the Bellagio Hotel and Casino around 4 a.m. on a Tuesday with a plan to put his belief to the test. He parked his Suzuki motorcycle near the valet stand, backing the bike onto a little service path so that its front tire pointed away from the casino. He wore dark coveralls, rubber gloves and a motorcycle helmet with the visor down. In his left hand, hidden inside his front pocket, was a gun.

“I didn’t intend to use it for anything other than deterrence,” Carleo recalls. “But you have to have bullets in it. Otherwise a gun is just a paperweight.”

In a booth just outside the casino entrance sat a lone security guard, a small elderly woman. Earlier in the night, Carleo had supplemented his adrenaline with several rails of cocaine and OxyContin – still, he somehow had the wherewithal to wave at the guard. She waved back. Inside the casino, Carleo kept close to one wall, moving past the banks of blinking and chirping slot machines, patron-less at this late hour.

Five days earlier, Carleo had robbed his first casino: the Suncoast, 10 miles off the strip, holding up its poker room for $19,000 in cash. The score had boosted his confidence; this time, the adrenaline seemed to heighten his perceptions and clarify his thinking.

“I felt like a predator stalking my prey,” Carleo says.

His prey was the high-limit craps table, the only one open at this hour.

Quickly, he closed the last 20 yards to the table and pulled out his gun. He could hear his voice shouting at everyone: “Move! Move!”

The stickman and dealers and players lurched back. One man dove to the side like a stuntman in an action film. There were millions of dollars worth of purple and yellow and red-white-and-blue chips arrayed in front of the dealer, and tonight Carleo could take as many as he could grab. He shoveled handful after handful into a backpack he wore backwards across his chest. Stacks of $1,000 and $5,000 chips spilled across the table’s green felt. After 15 seconds that could have been 15 days, something inside of him screamed out in alarm.

“I had big plans for that night,” Carleo remembers. “I was going to rob the poker room. I was going to smash and grab at the Cartier shop. But then fight or flight kicked in. And I flew.”

It was 200 yards back through the casino to his bike. An old knee injury and the extra layers of clothing he wore under his coveralls made his movements feel like running through surf. The motorcycle helmet that had served so well to hide his face now blinkered his peripheral vision so he couldn’t see whether some would-be hero was charging out from between the banks of slot machines to tackle him. When Carleo reached the heavy double doors, one of the valet attendants tried to block his path. Carleo waved the pistol and the man fell back.

Carleo gunned the engine and tore away down Flamingo Road into the desert night. He knew this heist dwarfed what he had done at the Suncoast, even if he didn’t yet know how big it was. In the backpack Carleo wore across his chest were casino chips worth almost $1.5 million.

Carleo, then 29, had moved to Las Vegas 16 months earlier to take classes at the University of Nevada, Las Vegas; he wanted to apply to medical school after he graduated. He took over a spare room at the house of his father, Las Vegas municipal court judge George Assad, and tried to keep his life on the straight and narrow. On a bulletin board, he pinned a photograph of his cousin Augie, dead from an overdose, over which he wrote the words “succeed for me.”

Carleo wasn’t without models for how a man might get ahead in life. “My father, my stepfather, my uncle – they all had money. Nice suits, nice cars, nice houses,” Carleo says. “But they all worked hard to get it. Me, I didn’t have time for that. I was too impatient.”

Carleo had spent his twenties in Pueblo, Colorado trading one new scheme for the next. He helped manage a family bar and limo business; worked as a DJ; dealt weed, ecstasy, pain pills and coke; sold roofing out of his truck after bad hailstorms damaged houses around town.

Eventually he began plowing all his money into buying up rental properties, signing for loans with balloon payments that would kick in after a couple of years. When the financial crisis hit, Carleo was left holding the bag on a series of underwater mortgages. Now deeply in debt, he was forced to sell his own house and let the properties go into foreclosure. In May of 2009 he filed for bankruptcy. A few months later Carleo scraped together $30,000 by liquidating what remained of his possessions and made the 12-hour drive to Vegas to start his new life.

For a couple of semesters, he held it together, managing to keep up his studies despite the distractions of his new city and a lingering addiction to OxyContin. He had a girlfriend, as well as a series of assignations with other women attracted to his dark Italian features, broad chest, and liberal supply of drugs. Still, Carleo was often lonely in Las Vegas, a condition he tried to assuage by spending more and more time in casinos. In late November of 2010, during a two-week break from classes, things for Carleo started to fall apart.

“Every day I would wake up and have to find something to do,” he says. “I wasn’t working, school was out, and I had all this free time.”

So, Carleo gambled. Maybe things would have gone differently if he had won, but he didn’t win. After losing half his bankroll over the course of a few days, Carleo took his last $12,000 and headed for a high stakes poker game at the Bellagio.

“These guys were just waiting for drunk tourists or assholes like me to put their money on the table.”

In a matter of hours, Carleo lost six grand. At around midnight, he switched to black jack, laying out all his remaining cash on the table.

“It was like the Alamo. That was going to be my last stand.”

In less than an hour, the dealer relieved Carleo of his last dollar. Carleo stumbled out of the casino to his car, angry and ashamed.

“I felt like a plane going down, just spiraling.”

When Carleo woke up the next morning, he was desperate to get back to even. He called around to different drug friends, trying to find someone who wanted to buy some of his store of OxyContin. A stripper he knew took $800 worth, and Carleo drove straight from the sale to the Bellagio, immediately putting the cash into a poker game.

At the table, Carleo fixated on a tall, skinny European kid in flip-flops and shorts who pulled $5,000 chips from a purple Crown Royal bag. Carleo knew he could take the kid, and he knew that if he could get his hands on that bag, the relentless pain that had overtaken him would stop. The idea, Carleo says, “became like an infection in my brain.”

There was, of course, another way for Carleo to get his hands on casino chips in a hurry. On every blackjack and pai gow and craps table were hundreds of thousands of dollars, just sitting there. It was a fantasy that has come to every gambler deep in the hole: What if I just reach across the table and grab them?

Two nights later, Carleo got a text message inviting him to a poker game at the Suncoast Casino not far from where he lived. The Suncoast was perfect for what he had in mind; it was 20 yards from the poker room cashier to a side entrance where he could park his motorcycle. “I couldn’t afford to play in that Suncoast game anymore,” Carleo recalls, “So I did the next best thing – I robbed it.”

He was in and out long before security or police could arrive. More important than the $19,000 in cash he made off with was the knowledge of just how easy it was to knock off a casino.

“It was a mountain to get over to make myself walk through that door. But once I did it, I knew anything was possible.”

He hit the Bellagio five days later.

By robbing the Bellagio, Carleo had achieved something he hadn’t been able to do in a decade of striving – he had made himself a millionaire. But, because he had stolen chips instead of cash, he was really only a millionaire inside the Bellagio casino. He would have to park his car in the casino’s garage, ride the casino’s elevator and walk the casino’s marble floors under the watchful eyes of thousands of cameras. He would have to hand the casino’s chips to the casino’s cashiers and hope that they would give him money rather than call the police. And because trying to redeem too many chips at once might bring unwanted attention, he would have to do it over and over again.

Carleo was back the very first night after the robbery.

“I felt like a big swinging dick,” he says. “I just jacked this place and now I’m going to cash in everything I took.”

Carleo could detect no obvious signs of trouble along the familiar route to the poker room. There were no Wanted posters with his picture on them. None of the dealers or security guards treated him any differently than the thousands of other gamblers chasing their fortunes at one table or another.

“Once I walked in and didn’t get bum rushed, I started to feel good,” Carleo says. “They had no idea who I was.”

Carleo found a seat at a high stakes poker game, buying in with hundred dollar bills from the Suncoast robbery. If the other players paid him any mind, it was only because they wanted to take his money. As the night wore on, Carleo slipped a few stolen $5,000 chips into his stack. The casino didn’t bother to track who won and who lost at poker, and, at the end of the night, though the cashier asked for his ID and player’s card, Carleo had no trouble cashing out.

“I wasn’t some new asshole who came in off the Strip with a whole bunch of chips,” Carleo says. “I was an old asshole with a whole bunch of chips.”

Carleo wasn’t content to lay low. The poker room was the safest place for his laundering operation, but it was only a couple of nights before he went in search of faster action. He found his way to the craps pit, to Table Number Five, the very same table he had robbed.

“I was just drawn to that table for whatever reason,” Carleo says. “I like irony, I guess.”

By then, the story of the “Biker Bandit” was all over the news – local TV stations aired security footage of Carleo in his coveralls and visored helmet jogging back through the casino to his motorcycle. As Carleo threw down a few bets for himself and a black $100 chip on hard eight for the dealers, it was all anyone at the table wanted to talk about.

“You think that guy will get away with it?” Someone asked.

“The guy’s fucking crazy,” said one of the dealers. “Of course he’ll get caught.”

“Are you kidding? He’s a genius. I guarantee you he’s long gone by now.”

For Carleo, it was surreal, like listening to the eulogies at his own funeral.

“It just gave me a thrill to be the one person there who knew what’s up,” he says. “Maybe it was narcissistic, but I really enjoyed playing at that table.”

Carleo did finally come to the attention of casino management, but not as a suspected criminal. Casinos like the Bellagio employ an army of professionals to lavish attention on high rollers, showering them with free meals and rooms and tickets to shows in hopes that they will stay longer and gamble more. Carleo was assigned his own casino host, who comped him steak dinners and a $600-a-night suite. He took to riding the elevator down from his room in a beige velour tracksuit, a golden Bellagio “B” embroidered on the chest.

Over the next several weeks, Carleo blew thousands of dollars on drugs and women – he claims that he spent $5,000 one night at a strip club on what turned out to be a four-hour hand job. The real drain, though, was the same as it had always been: gambling.

“I got to play the part and live the dream,” Carleo says. “There were times – I don’t want to say I didn’t care if I lost – but it didn’t matter to me. No matter what happened on the table, win, lose or draw, I’m still walking up to the cashier and cashing out 20 or 30,000 dollars.”

More than a million dollars of what Carleo had stolen were cranberry-colored $25,000 chips, which were only easily convertible for the highest of high rollers. Somewhere deep in the Bellagio’s computer system was a list of all the men and women who had ever gambled high enough stakes to have legitimately won so many big chips, but Carleo’s name was nowhere on that list. He was smart enough to know that trying to cash a single cranberry chip would raise suspicions, but beyond that, Carleo acted with very little restraint. He lived like his supply of stolen chips was not merely immense, but inexhaustible.

For New Year’s Eve, Carleo flew his old friend and former drug-dealing partner Alex up from Colorado for a visit. As the hours ticked down toward 2011, Alex and a woman Carleo had picked up earlier that day in the Bellagio gift shop watched Carleo get savaged at a blackjack table. “He was firing hard, $10,000 a hand,” Alex says. “And not winning.”

Alex and the woman tried to get Carleo to leave the table, but he told them to get the fuck away from him. Pale, a sheen of sweat on his forehead, Carleo couldn’t stop himself. When the New Year finally arrived and fireworks lit up the sky over the Las Vegas Strip, Carleo was still inside, hunched over the felt, chasing his losses until he had burned through all the chips and cash he had on hand.

“I think he lost over 100,000,” Alex says. “We were on a lot of pills, so we weren’t exactly thinking straight.”

By then, Carleo estimates that he was snorting or smoking at least eight 80 milligram OxyContin pills a day, mixing in a line of cocaine when he started to nod off at the tables. Alex says Carleo was in terrible shape, his skin sallow, his eyes sunk deep into their sockets. When it was time for Alex to fly back to Colorado, the two of them fought in the car on the ride to the airport.

“I told him that he needed to chill out on the drugs, that he was going to kill himself,” Alex says. “I didn’t get a whole lot of response from him except that yeah, he kinda agreed, he needed to chill out. We cried a little bit and then went our separate ways.”

The Las Vegas detectives assigned to the Bellagio case, Sam Smith and Jason Nelson, ran down a number of dead-end leads in their hunt for the “Biker Bandit.”

“We got a lot of tips like, ‘It’s my neighbor,'” says Nelson, “We’d ask, ‘Why do you think it’s your neighbor?’ and they’d say, ‘He has a motorcycle.'” Someone had pointed them in the direction of one member of a crew known for pulling robberies on motorcycles, but Nelson and Smith couldn’t put the suspect anywhere near the Bellagio on the night in question. A week after the robbery, a Salvation Army bell ringer had tried to cash in a $25,000 chip someone had dropped in his bucket, but he either couldn’t or wouldn’t identify the man who had given him the chip.

Then the detectives met the man they would eventually call “Leo.” Leo was a poker dealer at the Bellagio, and he said that he knew who the robber was. “Leo was this guy from Jersey,” Detective Smith says. “A really intense, really excited-type guy.” He reminded the detectives of the Joe Pesci character – Leo – from the Lethal Weapon movies.

Leo said that in the days leading up to the robbery, he had spoken with a poker player who had fallen on hard times and had shared a fantasy he had of stealing casino chips.

“Man, I’d like to just run over to that table and grab a bunch of those cranberries,” the poker player had said.

A week later, Leo saw the poker player again, only now he seemed to have come into a lot of money. He was sitting in games he never would have been able to afford before. Leo started playing detective, talking to other dealers and the cashiers to confirm his suspicion that the poker player was buying in with chips and not cash.

The man’s name, Leo told the detectives, was Tony Carleo.

Detective Nelson learned that Carleo held a class M license to drive a motorcycle, that he had declared bankruptcy a year before, that all of a sudden he had started gambling big money. “It was just red flag, after red flag, after red flag.”

Nelson also turned up one more troubling detail.

“Tony’s dad was George Assad, a sitting Las Vegas judge,” he says. “And I’m like, damn, if that’s the case, I better be right.”

On January 13th, they put a trap and trace on Carleo’s cell phone to log all of his incoming and outgoing calls. A week later, they pulled his player records. In the four years leading up to the robbery Carleo had lost a total of $2,900 at the casino. Since the robbery he had lost $105,000.

“But knowing who did it,” says Nelson, “and being able to prove who did it – that’s two different things.”

By this point, Carleo barely left the Bellagio, except to pick up stolen chips he had stashed with friends around town, or to unload cash into a safety deposit box at a nearby bank. At one point the box held more than $100,000 in laundered money. Now, just weeks after his pair of heists, he was down to $20,000. Of the $400,000 of easily convertible chips he had taken in the robbery, just a single $5,000 chip remained. As he emptied his deposit box out, Carleo said to himself, “You’re a fucking idiot.”

Carleo still had over a million dollars in $25,000 chips, but these were all but unusable. He fantasized about cutting a deal with a big name poker pro like Phil Ivey, someone the Bellagio could conceivably believe had access to a major bankroll. Carleo wasn’t the only one trying to solve the puzzle. On the poker forum TwoPlusTwo.com, someone had started a thread devoted to the Bellagio heist and how the robber might unload the stolen chips. Carleo followed the discussion closely, even going so far as to create an account on the site, choosing for himself the screen name “Oceanspray25” and listing his location as “Cranada.”

One day, Matthew Brooks, a recreational player in Virginia, posted the hypothetical question, “How many potentially worthless cranberries would you accept for a legit 5k chip?”

Almost immediately, Carleo began peppering Brooks with private messages.

“Would you be willing to trade 4 flags [$5,000 chips] for 3 crans [$25,000 chips] and if more were possible how many could you handle?”

Brooks for his part wasn’t sure how seriously to take him.

“I was just kind of dumbfounded that the person who did the robbery would be on that forum,” Brooks says. “It was way too high profile to do something like sell chips from a $1 million heist from the biggest casino in Las Vegas.”

In one of his messages, Carleo provided the number to a disposable cellphone, so Brooks called him up, as much out of curiosity as anything. During a 15-minute call, Brooks says, Carleo shared details about the robbery. Brooks asked for proof, and after they got off the phone Carleo went to his home computer and emailed Brooks a picture of two $25,000 chips resting on a piece of paper signed “Biker Bandit.”

Brooks forwarded the photo to the Bellagio and the Las Vegas Police. The IP address attached to the email revealed that it was sent from the house of Carleo’s father, Judge George Assad.

A few days later, Carleo was camped out at the Venetian, playing in a $1,500 buy-in poker tournament. He was overmatched by the young pros in their headphones and hoodies, but the cards were running his way. By the dinner break Carleo had enough chips that he thought he had a pretty good chance of cashing out on top.

As he was about to head off to find a bite to eat and a quiet place to do a rail or two of Oxy, a doughy, older man sidled up to his table. The man knew the poker dealer and made small talk, before finally introducing himself to Carleo. He was a doctor named Kian Kaveh and somewhere he had heard that Carleo had $25,000 chips for sale.

“Right then and there I should have left the country,” Carleo now says.

Carleo, strung-out on six weeks of drugs and gambling, made no connection between the doctor and what he had revealed to Matt Brooks on the phone. Still, he tried to be cagey, admitting only that he might know a guy who could get his hands on the chips. But before long, he had agreed to sit down in the Venetian’s Race & Sports Book with Dr. Kaveh, and a connected guy from New Jersey named Dominic who would be the buyer.

Whatever Carleo thought about the doctor, he immediately liked Dominic: tall, good-looking and full of the Italian-American swagger Carleo hoped to project as well.

Carleo tried to keep control of the conversation. He demanded to see Dominic’s ID, only relenting when Dominic asked to see his in return. When the older man offered him $10,000 in cash, then and there, for a cranberry chip, Carleo demurred.

“I don’t even know you, man,” Carleo said. “Slow down.”

So Dominic did. He explained a little about who he was: He worked in the loansharking business back east and was thinking of starting up a crew out here in Las Vegas. Maybe Carleo wanted to join up?

Carleo met with Dominic repeatedly over the next few days, and gradually came to trust him. Dominic was different from the people Carleo ran with in Las Vegas, and Carleo was hungry for human connection built on something stronger than a shared need to score drugs. They played blackjack together and traded text messages about which college football games to bet on. Over thousand-dollar dinners at Prime Steakhouse and in the backrooms of Vegas strip clubs, the two men hashed out the particulars of a deal for Carleo’s cranberry chips.

On January 30th Dominic slid a wine list across a restaurant table to Carleo, telling him, “There are some nice selections in there.”

Inside the menu were $10,000 in cash and smaller denomination chips. Carleo pocketed the money and passed a $25,000 chip back to Dominic. In restaurants and casino bathrooms around town, Carleo would sell his new friend a total of $100,000 worth of stolen cranberries over the course of the next two days.

On February 2nd, the two met one final time in a Bellagio bathroom not far from the poker room.

“I handed him the cranberries,” remembers Carleo. “I said, ‘There’s a couple extra in there for you.”

Something changed in Dominic’s face. He took the chips without a word, and disappeared back into the casino. Carleo could sense that things had taken a wrong turn.

“I just felt empty,” he says. “I knew shit was about to get bad.”

Bad shit arrived in the form of six metro police officers storming through the bathroom door, yelling at Carleo to get on the floor, wrenching his arms behind his back.

“Don’t resist!” The officers shouted at him.

Someone was punching him in the face. Carleo’s knee buckled sideways underneath him and his head landed hard on the cold bathroom floor.

“Dominic” was actually Las Vegas police officer Mike Gennaro. Dr. Kaveh was a friend of Gennaro’s, and also a casual poker player, who agreed to help initiate the sting operation on Carleo as a favor. Gennaro had learned his trade living undercover as part of an FBI investigation of a New York crime family. The money and chips Gennaro used to gamble with and buy Carleo’s cranberries, $50,000 in all, had been loaned to him by the Bellagio itself. (Dr. Kaveh was not compensated in any way for his role.)

Seven weeks after Carleo jogged out of the Bellagio with $1.5 million in chips, he was frog-marched from the casino through a service entrance and taken downtown to central booking.

His father, up for re-election as a municipal court judge, issued a statement not long after Carleo’s arrest: “I can say that as a prosecutor and a judge, I have always felt people who break the law need to be held accountable.” Nevertheless, just a week before Carleo pleaded guilty to the robberies of the Suncoast and the Bellagio, George Assad was voted off the bench.

Carleo was sentenced to nine years in Nevada’s Lovelock Correctional Center, the same prison that held O.J. Simpson. Journalists aren’t allowed official access, so Carleo puts me on his friend’s list. At our meeting in June, he has a slight paunch and a tired mien. Across a square wooden table, Carleo says the right things – how the robberies were a mistake, how getting locked up probably prevented a fatal overdose. At one point, he is suddenly overcome with tears when he thinks of how he let his family down. But just as often, he expresses regret for having failed to pull off his scheme.

“Look, I know I should have thrown those $25,000 chips away,” he says at on point. “But who can throw away a million dollars?”

It’s the oldest gambler’s lament: Why didn’t I just walk away when I had the chance?

In prison, Carleo bets stamps with other inmates on football games. He says he mostly comes out ahead, and that the small stakes are good for him. Still, before I leave for the 400-mile drive back to Las Vegas, Carleo asks a favor. “When you get to the Bellagio,” he say, “put $10 down on hard eight for me. And let it ride.”