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Making a fortune in Las Vegas is the modern American dream. Hold the lever, bet on black, let it ride. Vegas is a mecca for get-rich-quick acolytes. No hard work needed. A glittering, world-famous city of 2 million people built almost entirely on the concept of luck, promising all your problems can be solved and your dreams can be attained if you can just hit it big. Of course, it's not that easy. We've all heard the warning of the house always wins, that the odds are stacked against every player who puts their chips on the table. But there are ways to beat the house.

All right, straight out of Oceans 11. Casino heists are not purely the product of Hollywood's imagination, as the Bellagio Hotel in Las Vegas recently learned.

You could always just rob it.

A daring late night robbery at a big name Las Vegas Casino, where an armed bandit walked in and stole at least a million and a half dollars.

Now, robbing a Vegas Casino obviously takes a lot of nerve, among other things, but it has been done before.

It's something straight out of Hollywood. A thief is on the run with over a million dollars.

However, few Las Vegas casino heists are as brazen as the one that occurred in the early morning hours of December 14th, 2010.

It just seemed very bold. I remember people saying that it was ballsy. That was the technical term they used. And then it just got crazier.

The big surprise was the amount. One and a half million dollars. Wow. The thief would end up playing a game of cat and mouse with authorities. Setting off a truly gonzo series of events that could only happen in a place like Las Vegas. Over that time, he turned a nickname that would cement him in the annals of Sin City legends, the Biker Bandit.

Early this morning, at about 3:50 AM, the Bellagio Casino was robbed at gunpoint. The suspect arrived on a motorcycle in park just outside the North Valley, and the suspect was also wearing a full-face motorcycle helmet. He then entered the casino and went directly to a craps table where he confronted several patrons with a firearms. He told everyone not to move, and he took approximately $1.5 million worth of casino chips. The suspect then jumped on his motorcycle and exited westbound on Flamingo at a high rate of speed.

From Waveland, in Pegalow Pictures, this is the High Roller heist. I'm your host, Chris Sims.

All right. Go ahead, inflate it. Tony, question one. Take one, Mark. Please introduce yourself. My name's Anthony Carleo. My friends call me Tony, and some dickhead somewhere gave me the nickname the Biker Bandit.

Chapter One, Tony Mike.

I was born in Las Vegas, 1981. I have four sisters and three brothers. Some of them are fully related, some of them are not technically blood related, but loyalty makes you family, not blood.

Tony, or Tony Mike, as his closest friends call him, is the son of George Asaad and Vicky Carleo.

My father, George, he started off from humble beginnings. He was actually born in Syria, so he became a citizen through the naturalization process. He became a craps dealer and a blackjack dealer in Las Vegas, helped pay his way through college and law school. He's really worked for everything he's obtained in life and really the epitome of the American dream.

Tony's mom, Vicky, on the other hand, was from a big Sicilian family by way of Colorado. The couple met in Vegas where they started their family. But Unfortunately, George and Vicky's marriage ended soon after Tony was born.

He actually said I was the reason he went to law school. He had such a fight with my mother during my childhood and custody battle and all this. So he realized how much money these attorneys can make That really motivated him to go to college and get all that together.

Tony was barely a year old when his parents decided to split up. And while George stayed in Las Vegas, Vicky took the kids back to her hometown of Pueblo, Colorado. Pueblo, Colorado, my hometown, lies about 2 hours directly south of Denver in a semi-arid flatland where the Great Plains edge up along the base of the Southern Rocky Mountains. Much like the surrounding land, there's an inherent roughness to the town itself. The population is mostly blue collar, and it is known as one of the largest steel-producing towns in the United States. Many of the residents are hard workers, often grinding paycheck to paycheck. Pueblo also had the unique distinction of having more bars per capita than any other place in the US. Most open around 7:00 AM. A weekday breakfast beers are about as common as lattes in a big city hip neighborhood. After shift's end, most return to the bars until well into the evening. Brawls that spill into the streets are not uncommon. A callback to Colorado's earliest days in the mid-1800s. During the Colorado Gold Rush.

Pueblo was and sometimes still is like the Wild Wild West.

That's Nate Heston, an old buddy of mine, and Tony's. He's known Tony since he was 16 when they first started working together at the Carleo family's Italian restaurant.

There's a lot of hard work in families, a lot of generations that came here to work the steel mill or the farms.

By the 20th century, the town of Pueblo thrived. It became known as the Saddle-Making Capital of America America, and by the '20s, it was vying with Denver to become the state's capital. But a flood hit in 1921. It wiped out a third of Pueblo's businesses, and along with the receding floodwaters, went its chances of becoming the capital of the state of Colorado. Talk to locals like Nate, and a lot of them will tell you that Pueblo never fully recovered from that flood. The repercussions are still felt today.

Pueblo is definitely a tough town, in my opinion. Me and one of my cousins always joke around. There's that saying with New York, if you can make it here, you can make it anywhere. Well, we coined that with Pueblo. We're one of the very first people in the front range to have recreational marijuana. You go to Pueblo, Colorado, as long as you're 21, you can do almost anything.

Like many Italian immigrants who headed West, the Carleo family did well in Pueblo.

Gino is my stepdad. He didn't officially adopt me, but he's been in my life since I was one. He owned a little shop when I was younger. They called it merchandise market. Sold baseball cards, hats, T-shirts. Then he ultimately ended up going into real estate, and he's had a pretty successful career in real estate since then.

For a time, the family's name became synonymous with success in Pueblo. They helped revitalize downtown, flipping dilapidated buildings into lofts and restaurant spaces, all while preserving their historic charm. Here's Alex Blag, an old friend of Tony's and a proud Pueblo resident.

The Carleos were very well respected in town. As far as I knew in high school, I knew they were very big in the real estate and owned a lot of buildings downtown. I saw their signs all over.

And the family profited off of more than just real estate. They had side hustles, too, like operating cigarette vending machines in most of the bars around town. As the family became more successful, they also became more influential in town, and they soon cultivated a reputation, one that commanded respect, a family that you would be unwise to cross.

Another fun fact of Pueblo is Pueblo is one of the main hubs or pit stops, if you would, between Kansas City and Los Vegas. And so Pueblo had some connections a long time ago, too, as a hub for organized crimes and wise guys.

And because they were successful Italians in Pueblo, the Carleos were widely assumed to be, well, connected. Of course, if you actually asked a Carleo about that connection, they wouldn't know what you were talking about.

Back in the day, sure, in the '30s and stuff like that, you did. You had the Mafia, you had a heavy presence.

Here's Tony's younger sister, Lacy.

People try to tie the two together. You can't be successful unless there is something illegal that goes with it when that's not the case. We're Italian, and so sometimes people will get this misconception that you're in the Mafia or there's these awful ties, and none of it is true. It's just Pueblo folklore.

But none of that mattered to Tony. Not yet, anyway. He was a pretty happy kid. He watched his family grow from humble beginnings, and Pueblo was where he and his siblings set down roots. For them, it was just home.

Tony was not a troublemaker. Tony was a really good kid. Always funny, always joking, always nice, a very nice kid. He was the type of guy that would take up for somebody that was getting bullied or picked on. Just the kid that you want to be friends with. He was the best big brother ever. He was very protective of me. I remember he would wake me up at night when I was a kid. I was probably nine years old. And your magic cards a big thing at that time. And he would wake me up to come downstairs and play magic cards with him. I thought he was such a dork. I would put a pillow into my bed to make it look like I was there in case my dad got up and checked. I got caught every single time. We would play baseball in the street, use the mailbox as bases, and just had a blast. We had this swing set, and I remember Tony Mike took a skateboard down the slide. He thought that would be a good idea. And I was probably five, and he crashed and burned and just blood everywhere.

And he's my big brother, so I wanted to go help him. So I remember hooking up my wagon to my bike, and I rode over to pick him up and put him in it, and was screaming for my mother, but I thought he was going to die. We were the type of kids that wouldn't come into the house until the streetlights were on.

This is about where my story and Tony's first intersect. Running into each other at middle school and high school basketball and football games, I was a little older, and Tony became a younger brother in those early days. I had his back and he had mine.

He was a really good kid. As far as partying goes, never really drank. He was always having a good time, and definitely was entertaining in the life of the party, but was a really good kid, and pretty much had shit together.

He had good grades. He was the type of kid that didn't need to study and would pass a test, ace a test. Hated him for that. But no one ever looked at Tony and thought, One day he's going to get in trouble, and here we are.

I always knew I wanted nice things and money. You know what I mean? I had a job when I was in high school. I started umpire and baseball games. I actually really enjoyed that. If I had more time, I'd probably still do that. I got my license and family friend of ours owned some restaurants in town, so I got a job bussing with them and ultimately waiting tables. That's another thing that probably led to the social aspect of my personality. Can't be a dick and wait tables. You know what I mean? That was good for the tips and being social, and that's a bad thing. I've worked since I was 14, 15 in some capacity, so I knew I like money. I have to go earn money. So take your ass to work.

As Tony's social life grew, and he had some money to spend, the temptations of a tougher Pueblo lifestyle started to creep in.

So high school, I didn't drink a lot. We would sneak beers. I have my buddy, we have sleepovers or whatever. You get a couple of beers and steal them from parents or whatever. Nothing out of the ordinary. Ended up, did catch alcohol poisoning in high school, and I think that was probably a blessing. It really deterred me from ever wanting to get shit-faced. Didn't even smoke weed until I was 19. I remember a buddy of mine, we went golfing, and he had smoked a bit of the devil's lettuce before that. So we were golfing, and I hit the joint, man, and it turned into a shit show. After that, I was laughing and giggling, falling all over myself.

Full disclosure, that was me who brought the joint to the driving range back in the day. But we were just kids having fun at that point. There was an innocence to it all. We goofed around, we partied, and then we graduated.

I graduated high school in 2000, left that summer to go to UNLV. I had a girlfriend with me. My dad sent me up at the condo out there, which I was very grateful I was doing pre-law, so I might have been on the other side of the legal equation there. I just didn't enjoy it at that time, so I decided I wanted to come back to Pablo and get into real estate. Got my real estate license in 2002. I sold real estate for probably four or five years. I was never exceptional at it. I never really fully applied myself, but I made enough money to get by and wear nice clothes to work every day and do my thing. I would also maybe supplemented my income a a little bit at that point. I had other stuff going on.

Other stuff included buying into a friend's limo business, managing his uncle's dive bar, Gino's, DJing, and dealing weed. A series of side hustles that shared a special symbiotic relationship.

I was an opportunistic drug dealer, well caught. I have a social circle. I'm cheap. I'm not going to pay retail for something when I can buy it in bulk, break it down into smaller bags, take care of my friends, and make a few bucks. That's just the mindset I was at. I didn't think that I was doing anything that would even get on anybody's radar. It was like, if you and I are friends, you just call me up, Hey, man, can I get one? Yeah, I got you.

But the business did grow, and soon, Tony and his friend Alex were moving a decent amount of product.

This was later in our drug dealing career, but he had a basement full of about, I guess, around 250 plants or so. We were over there. It was around Christmas time. I just got in a really nice new bong that we call Percules, a little percolator bong. It's about nine o'clock at night, and we're getting extremely high while we're clipping this weed, of course, and smoking what we call Moon Biscuit, scraping the scissors and smoking it. We'll get a pounding on the door. Tony goes to his little foyer area and looks out the window and sees a light, pops back out of the foyer area and just looked at us. He was like, Help. I was like, Help, what? What are we going to do? We got 300 plans. We can't flush them all. But he was in a serious panic. I just never forget his face. Health. He thought it was a cop, but it actually was a UKS guy delivering a package at Christmas time. So I'll never forget that one.

But that indoor operation requires constant attention and financing. In a town the size of Pueblo, it can start raise eyebrows. Luckily for Tony, his family, knew people.

Somebody that had access to some information told my grandpa that I should probably get my electric bills under control or they'd have to come pay me a visit. My grandpa took me to breakfast one day and he said, Buck. A little birdie told me that your power bill needs to come down. So whatever you're doing, knock it off. I went, Thank you, pops. Went home and shut down shop, man.

With the weed business in the rear view, Tony began working at his uncle's and that exposed him to another under-the-table operation in Pueblo, one which would ultimately shape his future: backroom poker games.

There was a couple of poker rooms in town. You go in and there's two or three tables, and they had a dice game occasionally. It was funny, most of the people I'm playing poker with were these 50-plus-year-old people. You know what I mean? I was one of the youngest people there. But I enjoyed it. I wasn't good at it for quite a while. It was just fun. You know what I mean? Two, three nights a week, go play cards. I like to gamble.

As Tony dabbled in the underbelly of Pueblo, he got exposed to harder drugs, and eventually, he met the devil.

The first time I used the Oxy, I had a knee injury. I blew my knee out and somebody gave it to me, and it felt really good, and it took the pain away. But I have somewhat of an addictive personality, and that's a bad combination.

In the early 2000s, before the opioid epidemic was making headlines in America, it was already spreading through smaller cities like Pueblo, across the United States. It was nowhere, and then it was everywhere.

The first time that I ever had Oxy, was at a party with one of Tony's friends, and it was easy. It was a prescription. The guy had got hurt, and the doctor just gave that to him. I remember I went and got my nails done and passed out as she was doing my nails. I think I think a huge part of that is the prescriptions from doctors. I was in the dental field for 10 years, and I remember patients coming in that had an extraction. It's a Friday. You don't want to be bothered by that patient. So here's 20 Percaset. Take that. It's insane. And I think that's why it flooded so fast. It was easy to get your hands on because doctors were just writing it left and right and then go sell it.

Tony's close friend Alex experienced this firsthand. He was star athlete in high school until he was prescribed OxyContin by a doctor.

I actually was hooked on it without knowing. I was hooked on it my junior and senior year high school. I blew up both my knees. Doctors put me on it for two years straight. Long story short, end of my senior year, I graduated and lost my D1 scholarships and wasn't training anymore. So I decided to just flush my pills down the toilet and be done. At that point, I didn't really know what was on, but I was going through withdrawals when I was 18 and thought I had the worst flu ever. Didn't sleep for seven days. Long story short, I ended up drinking four bottles of Niquil just to get a nap. Lost my mind. Ended up getting put in a psych ward and diagnosed as bipolar. So I went from being all-American kid, straight A student to thinking I was crazy.

After being discharged from the mental hospital, Alex was prescribed lithium for what doctors believed as bipolar disorder. And so he wandered through the next few years of his life, a zombie, until his next run in with Oxy.

Went back to Tony's house, we're smoking weed, having a good time like we always do. My other friend gave me an OxyContin. And my other friend Justin said, Have you ever snorted that? I said, No, why the hell would I snort it? He said, Try it. I snorted it and just melted in the Tony's couch. And then from then on, it was just game over. I loved it. I didn't realize it until looking back 10 years on my life, that OxyContin really just sucked the soul and lied out of you.

That shit's the devil, man. It's the best feeling in the world. When you do it, it releases all the endorphins and chemicals in your brain. So you find yourself just going deeper and deeper down that rabbit hole and wanting more. And then again, that from my entrepreneurial side, devolved into me trying to buy larger quantities of them for cheaper prices and then sell them.

As it turns out, Tony's more legitimate businesses weren't doing so hot. He had accumulated debt, a lot of it. And his spending habits? Well.

I didn't respect money at the time, so I did spend it as I got it and didn't really plan or have any rainy day fund. I was living in the moment in that time. Had a motorcycle, had a boat, had some jet skis, had a big, lifted truck. Just living the American dream, as I say, but not really planning for the future. So the simplest solution for an exit strategy was just to file bankruptcy, get rid of all that debt that was hanging over my head. I figured going out to Vegas would have been a good opportunity to spend some time with my dad.

With nothing left for him in Pueblo post-bankrupty, Tony headed to Las Vegas to live with his father, George, now a well-respected municipal judge for the city.

A friend of mine and I drove out to Vegas, did the U-Hall thing, got all moved in. I did live with my father. He has a very nice house on a golf course out there, so I was set up for success. I had life by the balls, man. You know what I mean? I had a little money when I went out there. I think I had 30 or 40 grand. I ended up selling all my possessions and whatever I could scrape together.

It would be a fresh start, and Tony thought he'd find that at the University of Nevada, Las Vegas.

School was teed up. I had school paid for. The old man paying for that. I was actually planning on going to be a doctor. Ultimately, ended up in the pre-med program out at UNLV. I actually did well. I was a 4.0 student. I got two associate's degrees for whatever that's worth in a year and a half. I had a 4.0 GPA, all while addicted to OxyCon, as it were at that point.

Even Tony recognized the risk of his addiction when combined with his pursuit of a better life. And so he quit for real this time.

I actually did end up quitting. There's a substance called Suboxone. It's like a sublingual thing. You put it under your tongue and it blocks the mechanism in your brain that craves the key, per se, the OxyCon. I think I did that for a week and I was cool. I was clear and off of it. Then, a son of a bitch.

Now, a med student at UNLV, Tony Carleo seemed to be making progress in his new life in Las Vegas. He had a 4.0 GPA, a condo on a golf course, a healthy number in his bank account, and most importantly, he'd recently kicked his addiction to OxyContin. But it didn't last.

I went to a Christmas party the first year I was living in Vegas with some hot little Russian hairdresser I had met on plenty of fish. So we go to this Christmas party, and it's wild. So there's this girl in the back of the party, and she had to be 30, 40 feet away. I heard her say the fucking word OxyCon. Bro, my ears peaked up. It was like it was like sonar. I go holler at her. I said, Can you get these Oxis or whatever? She called this little drug dealer dude, and ended up getting some from him, and then that triggered it right there. And I was like, Hey, man, can you give me a hundred of these? Next thing you know, we're right down the rabbit hole.

Any proper trip down the rabbit hole in a place like Las Vegas is going to involve a lot of partying and a lot of gambling. And that is exactly what Tony did.

When you're on these drugs in the quantities that I was doing, it fucking altars your thought process, takes your whole life over. If I had a dollar for every minute I spent either procuring, selling, thinking, or consuming these pills, you know what I mean? I'd have been well off.

Around this time, Tony met a woman named Leila, another hairdresser, and quickly, the two of them hit it off.

I was working at Fantastic seeing him doing hair, and he become like, fine. And then next thing you know, we see each other. Drinking is our thing. We did drink a lot. I don't do drugs, but he did at that time. But I don't stop him. He could ask me to be in business. Who am I to say? But he did a lot of that. He just don't really care about his life or his health. I was concerned about that. But you can't tell Tony what to do if you don't want to do it.

An opioid addiction is more than just a habit you can't break. It's a force of nature, an evil force that systematically dismantles every aspect of life. And so it was for Tony. His grades plummeted, and he started to drift away from the family he was once so close to. Tony's sister, Lacy, remembers this vividly.

I noticed a change. I found pictures the other day. My niece was just born in March, the end of March. And so that was the first time he met her. And Tony looks great. And then six months later, Tony is gray and looks like he's about to die. So it was that fast of a change.

I neglected my family. You dissociate yourself from them. You know you're a piece of at that time, so you don't really want to bring any of that around. And then I ended up shit in the bed.

Tony was spiraling, and he was about to discover it was a long way down to the bottom. What happened next was the run to end all runs.

Gambling, you can either win or lose. So I am playing poker at the Bellagio. $5 small blind, $10 big blind. That's a fairly decent size game. You need to have some money to sit in those games. Might have been down four or five grand or whatever, then you start to chase. I think it was I'm playing blackjack, dude, and I don't know why I went there, but I was on a mission. I need to go get that money back, man. I lost 30 grand, ultimately. It was just desperation. It was a perfect storm, if you will, of a few different confluent events and circumstances. So then you find yourself no money. I have no friends out there, really. My social circle was here in Colorado. No drug. At some point, the drugs are going to run out. And you're just like, What's my play here.

And it was here, over $30,000 in debt, high, flucking out of school and alone, that my friend Tony first felt the itch. Not for drugs, not for gambling. This was a new feeling.

I remember there was some 21-year-old just looked like a dickhead, right? He's sitting across the table from me, and he gets whacked and needs to pull out more money. So he pulls out this Crown Royal bag. He pulled out a whole bunch of red, white, and blue chips, which I would later come to find out or refer to as flags, and they're 5K each. And I'm just like, Why does he have $100,000 chips in his hand. You know what I mean? It was just... It planted a seed, right? I had thought about robbing this dude, and I've never done any robbery. I'm not that guy at that point. But for some reason, it crept in my head. At that point, I'm like, Oh, you know what? Somebody might get hurt. I didn't want anybody to get hurt. I got away from robbing an individual in my head, if I'm going to do it, to, ironically enough, robbing a casino, which in my fucked up thought process, seemed like a better idea.

This idea, this single thought, would stay with Tony, infecting his oxyaddled mind, running through it over and over again. A hundred different made-up heists, each one smoother than the last. A thousand different mistakes to be made, each one corrected in his imagination, again and again until it just seemed inevitable.

Yeah, it was just an aha moment. I don't have any money now. I need money. And that was an easy out for me.

Coming up on this season of the High Roller heist, Tony Carleo embarks on a multi-crime spree that takes him all over Las Vegas, leads authorities on a weeks-long manhunt, and eventually lands inside the crown jewel of Sin City, living like a king.

I grab all the chips, I just turn around and book it. That adrenaline is through the roof, fight of flights kicked in, probably doing 100, 120, wheel that went off the ground. I'm grateful there was nobody on the road that night. It wasn't very busy because I probably would have been dead.

Doors don't lock in Vegas, and so it takes nothing for somebody to run in, hit a cart full of cash as they're doing the drop and run out.

He got back into my and he came into my room and he dumped the backpack full of chips onto my bed. It was a ton of money. It was a guy with a gun, and we got to make sure we get this guy so he doesn't do it again. It's hard to voluntarily throw some shit away that is worth a million dollars. There's some asshole in Vegas that could catch these chips for me. I just wasn't the right asshole.

This episode of the High Roller Heist was created and produced by Eli Kauras and Joshua Schafer of Pegalo Pictures, and executive produced by Jason Hoke of Waveland. Written and edited by Joshua Schafer, hosted and coproduced by me, Chris Sims, coproduced with interviews recorded by Nicolas Sanacas, theme music and score by Josh Eclebe, episode Assembly by Christie Williams, with sound design and sound mixing by Craig Plaquey. And host narration recorded by David Custard at CCM Studios in Denver, Colorado. Special thanks to the Denver Chophouse & Brewery. Thanks again for listening. And don't forget to follow or subscribe wherever you get your podcast and leave a review.