Sharp or Square - Covering The World's Best Gamblers with Writer Kit Chellel

Summary

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The Herd with Colin Cowherd

Sharp or Square - Covering The World's Best Gamblers with Writer Kit Chellel

Date: May 13, 2026
Presented by: Hard Rock Bet

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Episode Overview

In this captivating episode of "Sharp or Square," host Chad Millman and professional bettor/co-host Simon Hunter are joined by award-winning Bloomberg investigative reporter and author Kit Chellel. The conversation dives deep into Chellel’s new book, “Lucky Devils: The True Story of Three Rebel Gamblers Who Beat the Odds and Changed the Game,” exploring the hidden world of elite advantage gamblers, the technological evolution of betting, and the secretive subculture of those who have mastered the odds. Covering syndicates, legendary figures like Bill Benter and Tony Bloom, and the rapidly shifting landscape driven by AI, the episode offers rare insights into gambling’s past, present, and provocative future.

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Key Discussion Points & Insights

1. Philadelphia Sports Woes and the Betting Mindset

• Opening Banter (02:38–05:14)
  • Chad and Simon commiserate over recent crushing losses for Philadelphia sports teams (Sixers, Flyers, Phillies), setting a tone of resilience and perspective—traits mirroring top gamblers’ mentality.
  • Simon highlights the unique psychology of Philly fans and the burnout within the Sixers fanbase.
    • “Joel Embiid did turn around. But coming to this year, I think a lot of Sixers fans were kind of sick of the whole Joel Embiid experience...having another fan base come into your arena and be loud for two straight games…embarrassing.” — Simon Hunter (04:17)

2. Introducing Kit Chellel & The Making of “Lucky Devils”

• Kit’s Professional Background (05:14–07:47)
  • Kit’s reporting career grew from London’s status as a gambling tech hub.
  • The UK’s advanced legal framework and tech-driven betting industry led to unique opportunities for proximity reporting.
    • “London is kind of a hub of gambling tech. The explosion that's happened in the U.S.…that happened a long time ago in the U.K.…It’s kind of by accident, but also a little bit where I’m from.” — Kit Chellel (07:47)

3. The Godfather of Computer-Assisted Wagering: Bill Benter

• Legend of the Section (08:32–10:41)
  • Kit explains how Benter pioneered computer-assisted betting in horse racing, leading to billion-dollar winnings.
  • Benter’s legacy and longevity as proof of powerful algorithms in betting.
    • “Bill Benter, you can think of him as the godfather of computer assisted wagering…His total profits over 20, 30 years, you know, easily a billion dollars.” — Kit Chellel (09:27)

4. Elite Syndicates and the Secretive Sports Betting Subculture

• Covering Pro Syndicates (12:12–14:08)
  • UK figures like Tony Bloom and Matthew Benham operate legal, respected syndicates, more mainstream than in the U.S.
  • Despite public success, secrecy remains paramount to protect methods, edges, and avoid bookmaker bans.
    • “If you are the world's best gambler on tennis…it is very definitely not in your interests for anyone to know your name and what you do…” — Kit Chellel (13:18)

5. Why Top Gamblers Stay Under the Radar

• The Art of Secrecy (13:18–14:08; 24:41–25:51)
  • Revealing secrets ends edges; pros use pseudonyms or avoid publicity altogether.
  • Getting sources to talk takes persistence and often only happens as their careers wind down.
    • "None of the guys I wrote about wanted me to do it. They begged me not to. They didn’t want me to do this." — Kit Chellel (24:41)

6. The Traits of World-Class Advantage Gamblers

• Inside the Mind (21:08–22:38)
  • Highly technical, often with physics or maths backgrounds, but also street-smart and psychologically robust.
  • Emotional detachment critical—success is judged over 10,000 bets, individual wins/losses mean little.
    • “The top gamblers I’ve met simply don’t seem to care on an individual basis whether their bets pay off or not... It’s numbers on a spreadsheet…” — Kit Chellel (22:38)
  • Simon Hunter confirms:
    • “I don’t get ever get high or get too low. It’s a sickness...That’s why so many people fail at this job though, because you need to be wired this way.” — Simon Hunter (23:09)

7. Writing “Lucky Devils”: Motivation and Challenges

• How the Book Took Shape (19:29–21:08; 25:51–27:13)
  • The emergence of computer-assisted wagering, Vegas’ role in the 1980s.
  • Kit’s drive: love for secrets, hidden systems, and unraveling underground cultures.
    • “I love secrets. I love things that are hidden from view. I love the sensation of discovering how the world really works.” — Kit Chellel (26:08)

8. Spectrum of Advantage Gambling

• Book’s Breadth (28:00–28:58)
  • Covers personalities and systems across roulette, poker, sports betting—anywhere an edge exists.
    • “One of the truisms of gambling is if you can imagine it…somewhere in the world, someone’s trying it…This method works. It’s a mindset. It’s a sort of subculture.” — Kit Chellel (28:00)

9. The Appeal of Different Games & Most Resonant Stories

• Roulette, Benter, and Biased Wheels (29:24–31:42)
  • Kit’s affinity for roulette; describes a multimillion-dollar win exploiting a biased roulette wheel at Caesars in 2010-11.
    • “They identified this wheel tucked away in the corner of Caesars and they just hammered it for…16 or 18 hours straight. Same numbers, no breaks…they made $3 million that in one day…” — Kit Chellel (30:16)

10. Chasing and Losing Edges; Pattern Recognition and AI

• Evolving Edges (31:42–35:49)
  • Simon recalls benefiting from the spread offense in NFL and the lack of fans during Covid—examples of short-lived, highly lucrative edges.
    • “Life-changing moment was when the spread offense came from college to the NFL... There was a six, seven week period where that was big… And then Covid...huge advantage...” — Simon Hunter (32:12)
  • Transition to how AI is being used for both finding and faking edges—making the game dirtier and the arms race fiercer.
    • “There are huge, huge advantages right now because you can trick the book’s AI... It’s tenfold now...AI now for two, three years in the sports betting world.” — Simon Hunter (32:12–34:46)
    • “Bill Benter...he’s called it a new golden age... betting on horses. And it’s AI... He puts that into his large language model...he doesn’t even understand why it’s so good, it just is... This is the next frontier.” — Kit Chellel (34:46–35:49)

11. Lottery Syndicates & Syndicate Movie Pitch

• Lottery Exploits (36:04–38:21)
  • Discussion of global lottery syndicates (e.g., Jelko and the Texas Lottery), who analyze odds and buy all combinations for major rollovers.
    • “They will spend eight figures knowing that there will be a nine figure payout. And it’s worth it to them because it happens often enough.” — Chad Millman (37:02)
  • Kit dreams of a great documentary or feature film highlighting the real edge-seekers, not Hollywood’s caricatures.
    • “I’d love to watch the movie of the lottery syndicates... Not the Hollywood version...what it takes to build this career over the years.” — Kit Chellel (38:21)

12. Pattern Recognition Across Gambling Arenas

• Raffles, Ballpark Schemes, and Pattern Savants (38:47–40:05)
  • Simon discusses teams exploiting 50/50 raffles at games, hunting value in places with low participation.
    • “I know it sounds crazy to people, but this has been going on a long time…They are some of the greatest pattern recognition people I’ve ever met in my life.” — Simon Hunter (39:40)

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Notable Quotes & Memorable Moments

• On the Secret Nature of Elite Betting:

  • "If you are the world's best gambler on tennis, it is very definitely not in your interests for anyone to know your name and what you do for a living."
    — Kit Chellel (13:18)

• On the Psychology of Winning Gamblers:

  • “They are kind of unemotional people which brings its challenges when you're talking to them about their lives and their careers.”
    — Kit Chellel (22:38)

• On AI as the New Frontier:

  • “[Bill Benter] puts [decades of data] into his large language model and it sees things he can't see...this is the next frontier of betting is going to be AI.”
    — Kit Chellel (34:49)

• On Exploiting Market Inefficiencies:

  • “You’re just beating the out of the books both ways and they can’t adjust because...it’s an unknown situation.”
    — Simon Hunter (32:12)

• On the Universal Gambler’s Instinct:

  • “If there is a way to make money that involves math, a gambler's on it and you're always behind that person.”
    — Simon Hunter (39:58)

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Key Timestamps

• 02:38–05:14 — Philly sports frustrations and fan psychology
• 07:47–10:41 — Kit’s pathway, London as a gambling tech hub, and Bill Benter’s foundational role in betting algorithms
• 12:12–14:08 — Syndicates, UK’s open attitude, and stigma contrasts
• 21:08–22:38 — Core traits and psychology of pro gamblers
• 24:41–25:51 — The difficulty (and necessity) of earning trust among top gamblers
• 28:00–28:58 — The “Lucky Devils” book: concept, spectrum of games, approach
• 29:24–31:42 — Biased roulette wheel heists and their continued relevance
• 32:12–34:46 — Betting’s moving targets: NFL innovations, COVID, and the emergence of AI
• 34:49–35:49 — Bill Benter’s use of AI signals a new golden age
• 36:04–38:21 — Global lottery syndicates and the need for deeper storytelling/documentary
• 38:47–40:05 — Raffle exploitation and pattern recognition savants

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Conclusion

Kit Chellel, Chad Millman, and Simon Hunter offer an insider’s look into the rarely-seen world of the world’s top gamblers—those who have elevated mathematical mastery, psychological neutrality, and technological innovation into seriously profitable edges. With the advance of AI, the field is entering another transformative arms race—one requiring secrecy and constant adaptation. “Lucky Devils” is positioned as must-read reporting on those secretive, driven figures who have redefined the meaning of “beating the odds.”

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Recommended:

• Purchase “Lucky Devils” by Kit Chellel for a deep dive into this hidden gambling subculture.
• For more, follow “Sharp or Square,” part of The Volume Podcast Network.

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Transcript

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It says it.

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We do some retirement homes.

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Last night a blown call changed the game. This morning the Internet lost its mind and nobody's telling you exactly what happened. That's where Sports Slice comes in. I'm Timbo, and every episode we're cutting through the noise, breaking down the biggest moments in sports and giving you the real story behind the headlines. And we're going straight to the source. The athletes themselves, their locker room stories, their reactions in the moment, and the stuff nobody gets to hear. Listen to Sports slice on the iHeartRadio app, Apple Podcasts or wherever you get your podcast. And for more, follow Timbo Slice Life 12 and the TikTok Podcast Network on TikTok.

[Chad Millman]

Welcome to Sharper Square presented by Hard Rock Bet. We are part of the Volume Podcast Network. This is the show that Makes the squares sharper and makes the wise guys pay attention. I am Chad Millman. I am joined by my co host, my bff, my companion, my compadre professional better Simon Hunter. Hello, Simon.

[Simon Hunter]

Chad. How we doing, brother?

[Chad Millman]

Let me tell you something. I think we both wanted the Sixers to kick the Knicks ass. It did not happen. I think we both wanted the Flyers to move on. It did not happen. But I do think that. And by the way, the freaking Phils, like when we were doing the show, everything a couple weeks ago, everything was going great. It's taking a turn, my friend. A big, big turn.

[Simon Hunter]

Yeah. But I would say as a Phillies fan, I could put perspective that we, we literally beat both to two teams that owned us for the last 10 years in Boston and basketball and the Penguins and hockey. So I'm with you. No one wants to get double swept. It was very painful. Lost a ton of money, had some good times. Xfinity, I mean, it was fun two weeks ago in the city, but yeah, this was brutal. Especially the Knicks, obviously took over Philadelphia.

[Chad Millman]

Yeah, that was. That was kind of embarrassing. It was embarrassing because Joel Embiid said, hey, let's not let them take over. And then not only did they take over, they swept and did it in really dominant fashion. None of those games were close. It was kind of. I'm disappointed in Philly. You know, I love Philly. Like, I. I've got an affinity. Gonna spend a lot of time there the next six weeks with my kid graduating from Drexel. Plus I gotta go down for some. Some big presentations. He's doing like. I'm bummed by the city. Bummed out. Poor showing, Philly. Poor showing.

[Simon Hunter]

I would say New York has had zero success in any Sport in about 10 years. So it's not shocking if they have a little success in basketball that they're driving down 95. Coming to Philadelphia, potentially to go up 3, 0 or to go up 4. 0. On the flip side, the Sixers, of all the sports teams I told you, Chad, coming to this year, they are the most burned out fan base of all the fans. The fans die hard. Fans hate the organization, they hate the front office. And Joel Embiid did turn around. But coming to this year, I think a lot of Sixers fans were kind of sick of the whole Joel Embiid experience. And you know, that was great. It was a rallying. Like we needed to see that as Sixers fans. But you're right, that was having another fan base come into your arena and be loud for two straight Games embarrassing, but yeah, Josh Harris, sell the team. Go, go to Washington. He's just a terrible owner.

[Chad Millman]

Simon, I know you're feeling a little bit under the weather, so if people are wondering, you might just be a pretty face during most of the show. I think everyone who listens to this show knows that we hold the title of world's most literate sports betting podcast. We have had many authors on the show and we're going to do it again. We're not resting on our laurels, we're going to defend our literate betting podcast title which is why we're bringing on a very special guest who's got a brand new book. He's from Bloomberg Business Week, Kit Shalel. He is an award winning reporter where he covers sports betting, financial scandals. His pieces have been featured in the Wall Street Journal, the Washington Post, the Chicago Tribune, and the new book that I just mentioned. You guys are going to love this book. Lucky Devils, the true story of three rebel gamblers who beat the odds and changed the game. I don't think we've ever had a more perfect literature driven guest than Kit. Welcome to the show, brother.

[Kit Shalel]

Thank you, Chad. And can I just say how much I enjoy your British accent at the start of the show?

[Chad Millman]

Well, what's fun is listen, I love that you're on the show and I love that you have a legit British accent and I love that you're acknowledging mine. And that's very good. Suck uppery. What you, what you don't know is that Simon is from England originally. And so. And I love the name Simon. And there's that old SNL skit with Mike Myers where he's pretending to be a British kid in the bathtub and his name is Simon. So this is my sentimental way of bringing back that sketch from snl and I hope I don't offend the Brits. And clearly you're not.

[Kit Shalel]

We used to it.

[Chad Millman]

Kit, before we came on the air, I said to you that I feel like you're living the exact life I wish I lived in, that you are living in London and you are writing big stories for a major global publication on the exact subjects that I am most fascinated by. Tell me why you're living this life.

[Kit Shalel]

Well, you may not know it, but London is kind of a hub of gambling tech. The explosion that's happened in the U.S. in the last five, six, seven years, that happened a long time ago in the U.K. we've got a very developed betting market. There's lots of betting startups. Some of the Biggest online bookmakers are British run and British headquartered. I stumbled into this world because of my proximity to all that. And my first story about Bill Benter, the horse racing genius billionaire out in Hong Kong, there was a London connection to that too. Quite a famous London investor had invested in one of the companies that came from the Hong Kong betting scene. So it's kind of by accident, but also a little bit where I'm from.

[Chad Millman]

Explain who Bill Benter is, because we just did a derby show a couple weeks ago and the concept of computer assisted wagering came up. And Simon knows this and I know this, and a lot of our listeners know that around the world, it's not American football that is the biggest sport to bet on. It's soccer, European football, and then horse racing. And someone like Bill Benter, and there are other people like him, have dominated that for years, running very sophisticated algorithms, using very sophisticated models. And it's been very under the radar. Are outside of the sports betting world. People like you have done stories about it, but give, give some background and sort of Bill Benter, specifically in that world and how much bigger it is than anyone really knows.

[Kit Shalel]

Yeah, Bill Benter, you can think of him as the godfather of computer assisted wagering. I mean, he really, I think he really was the first to do it in a horse racing setting. Bearing in mind that when he started in 1980, I think he first started looking at this. You know, most people didn't even have access to a computer, but he was a card counter at the time and he was a very mathematically technologically minded guy. And his big idea was, you know, let's apply that big data method to horse racing. It's, you know, horse racing is driven by numbers, performance, speed, as you guys know. But he was the first one to really take it seriously. And by that I mean he took $150,000, moved to Hong Kong, where he'd never been before in his life. He was living in Vegas at the time and started his business. And you know, 50 years later, 45 years later, however long it is now, he's still doing exactly the same thing. He's still using a computer to bet on horses, which tells you that he's onto something. You know, he didn't just have a couple of good seasons. His, his total profits over over 20, 30 years, you know, easily a billion dollars. So he's kind of the king of computer assisted wandering.

[Chad Millman]

Yeah, it's a fascinating space that is now, I think, for a variety of technological reasons, becoming a bigger and bigger deal here. In the us. Simon who I'm not going to make him speak just because I know his. He's in agony with some, some teeth issues today, but he's a pro and he doesn't miss a show even if he's not going to say anything. I know that you know he works for a syndicate, right. And the group that he works for, he's talked about has increased the amount of people dedicated to working on horse racing because the amount of money to be made there is getting bigger and bigger in the United States because of the technology. You being in the uk, there have been people running syndicates forever and they are legitimate, respected business people. I'm thinking specifically about someone like Tony Bloom, right, who runs a company called Star Lizard or Matthew Benham, who owns a. Who owns a company that is dedicated to the sports betting space but also owns a Premier League team as Tony Bloom does. Living in the uk Describe sort of what it's like when you try to cover people in this space who are doing something that they know they have secrets about, but it's still a legal business. What is it like to try to cover that?

[Kit Shalel]

Yeah, in the UK there's less stigma about gambling. I mean, we've been doing it a lot longer and we never had the extent of organized crime involvement in betting as you guys did in, particularly in Vegas when the mob were all over it in the 1950s, 60s and 70s. So it had a kind of stigma of criminality and darkness to it. It never really had that here. So it's much more mainstream. That said, the two guys you mentioned, Tony Bloom, owner of Brighton and Hove Albion Football Club, Matthew Benham, owner of Brentford Football Club, those guys are professional gamblers. They made their money using tech driven bets in the 1990s, particularly on international soccer. Now most people in the UK don't know that that's how they made their money. They're sort of vaguely described as doing sports analysis or sports data. But the knowledge that there is this elite class of people who run hedge fund like operations to bet on sports, I still think it hasn't quite seeped out into the consciousness in the UK and maybe not in the US either.

[Chad Millman]

Why do you think that is?

[Kit Shalel]

I think part of it is that when you're really good at this, you don't talk about it. I mentioned this in the book. If you are the world's best gambler on tennis, it is very definitely not in your interests for anyone to know your name and what you do for a living, it causes all sorts of problems. Not least of which, you're liable to be excluded from any betting platform you're using. No one will take your bets. But there's other reasons, too. I mean, just like in financial markets, any edge, any advantage you have has a time limit. It's a ticking clock. As soon as you get your advantage, eventually the rest of the market will wake up to it. So this sort of ingrained secrecy at the very top level here, that meant that those stories haven't really been told extensively. At least they hadn't a few years ago.

[Chad Millman]

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[Shaquille O'Neal]

People never believe me when I say I'M just like them. I take out the trash, do dishes, and I struggle with moderate obstructive sleep apnea, or osa. And a lot of adults with obesity also struggle with moderate to severe osa. You know, those scary breathing interruptions during sleep, the loud snoring, choking, and daytime fatigue. I knew I had to talk to my doctor. Don't sleep on the symptoms. Learn more at don'tsleeponosa.com this information is

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What's up, guys? This is Clifford Taylor the Fourth, and on my podcast, the Clifford Show, I'm bringing you conversations about all kinds of stuff, like being an Internet famous referee.

[Kit Shalel]

We're in the middle of a game.

[Simon Hunter]

This linebacker, this linebacker walks up to me. He goes, hey, ref, my mom wants you to wave at her. What?

[Kit Shalel]

Time out, quarterback on offense. Blue 42.

[Simon Hunter]

Hey, ref, my mama wants you to wave at her.

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[Kit Shalel]

Where's she at? Hey, Ms. Parker.

[Simon Hunter]

Listen to the Clifford show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

[Chad Millman]

All right, so Lucky Devils, name of the book I was at a conference in a year ago in May. Listeners of the show know that I've been reporting a book that comes out next year called the Number about this world of sports Betting. One of the guys I Spoke to a former Australian bookmaker. We were talking about the differences. You just mentioned stigmas, right? The differences between, say, the UK or Australia and the United States. And he said to me, look at Tony Bloom, one of the biggest betters in the world, runs a huge company that is focused on still winning in sports betting, owns a Premier League team and is a member of the, you know, has been anointed a member of the British Empire. And then he said, and look at Billy Walters. He went to jail. So I know Billy is a part of your book Lucky Devils. Explain a little bit about the book and how you came to the idea.

[Kit Shalel]

Well, I sort of stumbled into this world of computer assisted wagering, the elite people who, the 1% who can do it really well. And I wanted to understand how they came to exist. You know, how do you get a job like this, especially in the 1970s and 80s when no one had a computer? How is it that these guys develop this very unique skill set? And I sort of just traced back their stories to a particular place in time, which was Las Vegas in around the 1978, 79 through to the early 80s when gambling science kind of exploded. And it was a combination of different things happening. Lots of very smart young people coming to Vegas to make a living, having read books about card counting, but also the ready availability of computing equipment for the first time and a sort of general niche interest in the science of probability for the first time. I want to tell people about this amazing conference that happened in, in Lake Tahoe in 1981. And it brought together like some of the greatest minds in science and probability and mathematics of the era. And they were talking about blackjack. You know, there were guys, There were European PhD professors presenting statistical analysis of every card counting system to see which one was fractionally more effective than the other. And so the very top end of this activity, they came from that. That's the world they came from. I kind of wanted to understand how they came to exist. And hopefully I, and I do a decent job in the book of showing what it takes to reach that top level at least.

[Chad Millman]

What did you find? What were some of the traits that connected people like this who wanted to apply that skill set to betting, whether it's sports betting, blackjack, casino games, table games, whatever.

[Kit Shalel]

Yeah, there's definitely a type. I think maybe a type that is common in any area of endeavor where there are exceptional people, whether it's academia or politics. But so the obvious ones would be very technically minded mathematical people. They're math nerds, right? They're the guys who score very well in math score throughout high school. Often they're guys who have studied physics or one of those technical subjects at college. They have that level of ability. But what makes them unique I think is that they can't just be white tower, ivory tower academics. They have to be able to apply their skills in a real world setting, a casino or a betting market. And that's a whole other world. So you need psychology for that. You need street smarts for that. The other main characteristic they have is this kind of cold bloodedness. The top gamblers I've met simply don't seem to care on an individual basis whether their bets pay off or not. They are only interested in their performance. Over 10,000 bets. The individual bets mean almost nothing to them. It's numbers on a spreadsheet, you know. So they, they are, they are kind of unemotional people which brings its challenges when you're talking to them about their lives and their careers.

[Chad Millman]

I wish Simon could speak right now because obviously he's a professional. Better Simon, take yourself off mute because I like you live in this world. You see these traits and we talk about on the show all the time. You're not making an individual bet. You're. You're making the bet that is going to win the majority of the time. And you can't get too up or two down based on that one bed at that one time.

[Kit Shalel]

Yeah.

[Simon Hunter]

And I, I do try to do a little performative on the show. I'll be honest because I, I don't care. Chad knows this. I really don't like I, it hurts when I lose. No one wants to lose money and I care fans. But I told you, win or lose, I'm already on to the next week. That's literally the job. That's what makes me good at my job. It's like I don't get, ever get high or get too low. It's a sickness. I agree with what he's saying. Like it's not. You shouldn't be wired this way. That's why so many people fail at this job though, because you need to be wired this way. I mean I've never met a professional who didn't go back to zero. They always go broke because you need to learn before you succeed. And yeah, I've told Chad a million times I've. I don't use my real name on the show. No professional better. I could beg them to come on the show. There is nothing I could give them to come on this show. There's nothing to gain. So, like, Chad's doing a book right now, finding these professional betters. It's. It's hard to get pros to talk, but some guys love to talk. Like, so if Chad can find the right pro that likes to talk, that's no problem. But that's one out of every thousand. Maybe, like, they just. This is not a job where I want to tell you what my secrets are or who I know. It's just, that's the line of work. So, yeah, that, you know, that whole aspect of it, what you guys are trying to do, it's probably much harder than people realize trying to write gambling books, because it's not. There's no. There's no game to me other than ego to give you my story and my secrets. So it is very tough to pin down sports betters and get good information.

[Chad Millman]

Well, look, that speaks to go. No, you go. You go. You're the guest.

[Kit Shalel]

I was just gonna say that none of the guys I wrote about wanted me to do it. They begged me not to. They didn't want me to do this. I. I thought it was worthwhile doing for people to understand what the top level really looks like. But no, they didn't. They didn't want me anywhere near it. I had to sort of cajole them along.

[Chad Millman]

How do you think you finally convinced them?

[Kit Shalel]

I'm annoyingly persistent. That's part of the answer. I just don't go away trade secret. But I think mostly they're all towards the end of their careers, if not at the end of their careers. So they're not quite as much sensitivity around what they do as they used to be. And also because I'm so obviously an enumerate doofus, there was no chance of me stealing their system. I simply wouldn't understand it. I could see Bill Benter's proprietary algorithm. It would mean nothing to me. I was more interested in, like, the making of him. You know, like, if you read a book about Michael Jordan, it's not because you think you're gonna, you know, nail his jump shot. It's not going to happen. But you. But you want to understand where he comes from, what it takes to be him. So that's what I was going for, and that was a bit of an easier sell.

[Chad Millman]

Did you get into this because of the proximity? Was there a natural affinity for this industry before? Or were you just an enterprising reporter looking for a beat where you might find some juicy stories and no one else was looking? I love.

[Kit Shalel]

I love secrets. I love things that are hidden from view. I love the sensation of discovering how the world really works. And I sort of, with gambling, there was this whole layer behind what most people see when they go into a bookmakers or when they open their laptop to bet. There's a whole layer behind that that's hidden from view, full of fascinating stories. And I love the idea that this guy, Bill Benter, you know, maybe the most successful horse racing better of all time, had been doing his thing for 40 years and really no one knew who he was. I spoke to a racing consultant in the uk. This is a professional whose job it is to analyze horse racing. He told me that it was impossible to make money betting horses. It simply couldn't be done. So I was just intrigued by the fact no one knew this existed. And I also, I like the idea of, you know, taking on a challenge, this difficulty, just because it's there. You know, I was fascinated by the mindset that takes a smart young person to say, I'm going to quit my college degree, I'm moving to Vegas, I'm going to try and make as a professional gambler, I'm going to lose money for two years and I'm going to keep going because I believe in the science that strongly.

[Chad Millman]

Do you? You know, it's funny, I would say 10, 15 years ago, I was in Vegas at a sports betting conference and I knew a reporter who was there. There was a whisper that Bill Benter was going to be at the conference and he came to Vegas just on the chance he might get to see Bill Benter because like you, he wanted to do a story about this guy. What character, when you were thinking about the book Lucky Devils drove you to say, this is a book. I got to get in front of this, I got to get this to a publisher.

[Kit Shalel]

It wasn't one character. I think it was the fact that once I discovered Bill Benter in horse racing, I started looking at other, other types of wager. And, you know, one of the truisms of gambling is if you can imagine it, somewhere in the world is somewhere, somewhere in the world, someone's trying it. You know, anything you can think of. There's a system for any game you can imagine, even the lottery. This has had a bit of press in the US recently that these lottery syndicates run by the same sorts of people that you and I know. Yeah, the idea that any, any game of chance can be, can be defeated with this method and enough persistence was fascinating. So what I, what I wanted was to show the spectrum of advantage gambling. You know, I didn't. I didn't just want to do horse racing. I didn't just want to do sports betting. I wanted to show that this method works. It's a mindset. It's a sort of subculture. So I just found three characters who cover the spectrum from roulette through to poker, through to sports betting through to horses and various other things.

[Chad Millman]

Was there an angle or a game as you were doing this that you felt more connected to, Whether it was sports or roulette or horses, that was the most appealing to you, that felt the most natural for you to sort of connect with?

[Kit Shalel]

I'm a roulette guy. I love roulette. I think there's a visual poetry about roulette. It just looks and sounds great. It's fun, it's simple. It's beguilingly simple. The times I've been to Vegas, before writing this book, the only bets I made were at the roulette table. You know, I never really played blackjack. You know, I was too intimidated to do poker, and I'm a terrible poker player. But, yeah, roulette, I used to go and just. Just put my bankroll on black. That's my casino bet. It actually isn't as stupid as it sounds because, you know, at least you have some chance of walking away with some money.

[Chad Millman]

What's the story from the book where you felt like this is what's going to resonate the most with people? And then what has resonated the most with people?

[Kit Shalel]

People seem very, very drawn to Bill Benter. And I kind of get it. It's because. It's because he's one of the world's good guys. You know, he. Not only did he do this amazing thing in quite a sleazy environment, but I'm not talking about gambling per se. I'm talking about Hong Kong in the 1980s. You know, it was. Yeah, yeah, it was a wild place. He made a living doing this impossible thing. But then, you know, as he started making tens, hundreds of billions of dollars, he sort of dedicated himself to philanthropy and to giving it back. And, yeah, his is a feel good kind of story of someone overcoming long odds. The story I like most from the book is a recent one. It was 2010, 2011. And it was my roulette specialist who got a big win in Caesars Caesar's casino. They had a biased wheel system, which I probably don't need to explain. You're just looking for wheels that are a little bit predictable. Betting the same numbers over and over again. Amazing that that still works. You know in billion dollar casinos with all the technology they have, you can still do bias wheel play. But they identified this wheel tucked away in the corner of Caesars and they just hammered it for I believe it was 16 or 18 hours straight. Same numbers, no breaks, just bet after bet after bet. The only thing that stopped them was when they got too tired to continue. I think they made $3 million that in one day doing that. And yeah, I love the idea that that still works in the modern mega casino era.

[Chad Millman]

Well, it is amazing that when you find the edge, when gamblers find the edge and you can ride it so aggressively, you can't stop because you don't know how long it's going to last. It's like you've got to grab and go as much as you can and like what's the longest you've ever had an edge? Last

[Simon Hunter]

life changing moment was when the spread offense came from college to the NFL. Like I just timed it perfectly where my model was ahead of it than the sports books. Like I knew there was going to be more points and I knew earlier in the season before the defenses could adjust, there's gonna be more points. So there was like a six, seven week period where that was big. And then Covid, I don't know if you remember Covid, there was no fans for football. Yeah, that was a huge, huge advantage where it's like there is zero crowd noise. Why wouldn't the offense excel here? And I remember for the first couple weeks there was a ton of points like those little things like that. It sounds simple but yeah, like got tons of money down because it's like oh my God, the books are, they're sleeping here on this one. And then they over adjusted and we hit it the other way. We started taking the unders and that's. That to me is the best. You know, you're just beating the out of the books both ways and they can't adjust because they can't find that middle because it's. They don't know what to do. It's an unknown situation. Their computers, which they rely on, can't predict a model that's never had fans before. So those are little moments like that in Sportsman that's just like this is, this is the dream. So like we talk about all the time those advantages now with AI. I can't even talk about it. There are huge, huge advantages right now because you can trick the book's AI. So there's moving lines, there's fake Money. I told you all the time, Chad. There's times where you bet sides just to move the number so you can go heavy on the other side. It's like tenfold now because the books will overreact, especially AI now to certain accounts betting. So they'll move numbers based on certain accounts. And professional betters know that. So it's. Again, there's a whole other world right now where people are just going to start learning AI People think it's just come around this last couple months or last year. People have been using it now for two, three years in the sports betting world. So there's a lot of dirty secrets right now with AI Especially Judd.

[Chad Millman]

It's interesting you say that because a lot of people I've spoken to are professional betters. They use AI but the biggest impact it's had for them is, is sort of making them more efficient in doing the work they're doing. So explain what's different than what I'm being told.

[Simon Hunter]

No, that's true. Like I told you what, something would take me 12 hours or a day to put in all the numbers and all the data. It's already programmed. It's doing the work for me. So that's an advantage. But I'm saying more so of using AI to make bets for you. Right. Like it's. Is again, I don't want to get too into it, but it's. It's a dirty game. Right. There's. It's accounts get banned.

[Kit Shalel]

Maybe I can. I can. I can share something from the book.

[Chad Millman]

Yes.

[Kit Shalel]

You know, Bill Benter, the godfather of computer assisted wagering, guess what technology he's been using in the last three years. He's called it, you know, a new golden age of his. Of his career, betting on horses. And it's AI he previously, he built his model piece by piece, largely with guesswork and trial and error. Now he does have 40 years worth of very good data that probably no one else in the market has access to. But he puts that into his large language model and it sees things that he can't see. And he said often he doesn't even understand why it's so good. It just is. Yeah, this is the next frontier of betting is going to be AI. The, the operators and the bookmakers are already using it. And it's going to be another arms race like we had in the 1990s with card counting. You know, it'll be betters on one side using their systems and, you know, the bookmakers on the others trying to use their systems. To stop them.

[Chad Millman]

Have you thought about how you're going to cover AI and sports betting or betting in general for Bloomberg without giving away any secrets of what you might be working on that is coming down the pike.

[Kit Shalel]

I don't have any gambling stories in the pipeline. I mean, I've spent seven years on this now and I feel like, I don't know, I put, I put all the things that I learned about gambling I feel like I put in the book. I would love someone else to pick up the baton though. I mean, like, there's great stories out there. I'm still waiting for the really good lottery syndicate story. I want someone to do that. You know, I know that there are these teams, Chad, I'm sure you know who's behind them. Now we all know who's behind them, but they do this around the world. It's not just in Texas, where we've read about it. They go and find these big rollover jackpots and they hammer them and they buy every combination and it's a major operation. It's like thousands of manners they have to spread out across all these little shops and they sometimes lose. You know, sometimes you can go to Germany or somewhere and, you know, drop 10 million euros buying tickets and still lose your money. I think that's a fabulous story. I'd love someone to do that.

[Chad Millman]

Well, look, what you're referring to, I

[Kit Shalel]

want it to be told from the point of view of the gambling.

[Chad Millman]

Yes. What you're referring to, if people don't know is there is a massive gambler, his name is Jelko, who the Wall Street Journal covered this story and he led a group that was able to essentially manipulate the Texas Lottery and win millions of dollars because of it. And now the Wall Street Journal did a great story about this about probably about a year ago and it is now led to a lot of rules changes for how the Texas Lottery is run. But this is a group and there are several of them, like Kit says, that are doing this all over the world and they basically calculate the investment of their time and they will go to get lottery machines. They will work with the people who produce the lottery tickets and they will essentially buy a ticket for every number that's available. And they will spend eight figures knowing that there will be a nine figure payout. And it's worth it to them because it happens often enough. It's, it's fascinating, but it is sort of. Kit, the next level of what you're talking about in your book is these people who are using the math and the cold blooded nature of how to make money to execute against these ideas. It's great.

[Kit Shalel]

I'd love to watch the movie of the lottery syndicates. Wouldn't that be great? I think that'd be such a fun watch. I mean, it's great that serious books are being written about gambling now. I think it's long overdue. I'd love to see a really good, entertaining Hollywood movie that captures this mindset for what it really is. Right. Not the Hollywood version, not the, you know, not the all come. It all comes down to one night. What it takes to build this career over the years. I think that'd be a great film.

[Chad Millman]

I agree. Simon, what are you gonna say?

[Simon Hunter]

Yeah, just saying it's the lottery. I say it all the time. There's so much stuff I've heard over the years. The biggest next one too is these 50, 50 raffles. People go to sports games at, I know syndicates that for the last 20, 30 years have gone to these sporting events and now they're hyper focused on, you know, ballparks that people don't go to. Right. Like empty ballparks is a big advantage for them. College football is a big one for them. So I know it sounds crazy to people, but this has been going on a long time and more stories keep coming out and yeah, it's like I always say, if there is a way to make money that involves math, a gambler's on it and you're always behind that person. That's why you need luck. Whether or not playing for luck, they're playing some type of rhythm, some type of math, looking for patterns. And that's most the guys I look, they are very tech savvy, they are smart with math, obviously, but they're some of the greatest pattern recognition people I've ever met in my life. Like, it's just incredible. Like some guys, savants do, you walk into a place, this guy goes, they have 10, you know, fire alarms in here. It's like, why do you even, why even looking at that around this room? Like, it's just, they can't help themselves, right? They're always looking to add up the numbers and different objects in the math. And that's again, that's where you're going against people when you, when you're betting into these markets.

[Chad Millman]

Kit Shal, Bloomberg. The book is Lucky Devils, everyone go buy. If you're listening to the show, there's no reason you shouldn't be buying this book. It's exactly what you want to read. About, especially while we're waiting for football to come back. But great, great book. Lucky Devils. Kit Shalel Bloomberg this has been Sharper Square part of the Volume Podcast Network. Watch or listen on YouTube at Sharper Square like this video. Subscribe to the channel. Download us from Spotify, Apple Pods wherever you get your pods. Rate, Review Subscribe. Leave us five stars. Say whatever you want. Feedback is a gift. Till next time. Love you.

[Kit Shalel]

Last week was last week.

[Simon Hunter]

This week was this week.

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Next week will be next week.

[Chad Millman]

And now, Superhuman Shack.

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Another podcast from some SNL late night comedy guy, not quite on Humor Me with Robert Smigel and Friends. Me and hilarious guests from Bob Odenkirk to David Letterman help make you funnier. This week, my guests, SNL's Mikey Day and head writer Streeter Seidel helped an acapella band with their between songs Banter.

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We do some retirement homes.

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Those people are starving for banter. Listen to Humor Me with Robert Smigel and friends on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

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