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

Welcome to Sharper Square, the place that sharpens the so-called squares and makes the pros listen. Philly got steamrolled this week, and as much as I love that city, watching New York take over our building was a gut punch.

It stung getting swept by teams that have haunted us for a decade, and the Knicks takeover was brutal. I had fun early, lost a lot late, and the city felt it.

Embiid said not to let them in, and they still owned the place, which was hard to watch with my Philly ties. Tough scene, Philly, tough scene.

New York’s been starving for wins, so of course they drove down the highway when they smelled blood. Sixers fans are burned out on the front office, and I’m still on the 'Josh Harris, sell the team' train.

Simon’s a gamer even under the weather, and our 'world’s most literate betting podcast' streak continues with today’s guest. From Bloomberg Businessweek, Kit Shilal is here with Lucky Devils, a killer book about three rebel gamblers who changed the game.

Thanks for having me—and I appreciate the attempt at a British accent.

I’ll retire the bathtub bit, but tell us why you’re living my dream in London, writing big gambling stories for a global outlet.

London’s a gambling-tech hub with a mature market and a web of startups, so I fell into the beat by proximity. My path ran through a Hong Kong horse story with a London investor link, and it pulled me into this hidden world.

For listeners, set the stage on Bill Benter and computer-assisted wagering.

Benter basically pioneered algorithmic horse betting, moving to Hong Kong with a stake and turning decades of models into enormous long-run profits. He proved you could industrialize the edge and keep it alive for years.

Here, syndicates are doubling down on horses, and in the UK you’ve got figures like Tony Bloom and Matthew Benham. What’s it like reporting on people who are legal but secretive by design?

We’ve got less mob-era baggage, but true elites keep quiet to protect bans and edges that decay once exposed. The public still doesn’t grasp that some run hedge fund–style operations to bet sports.

Your book lands in that gap; think Bloom being honored versus Billy Walters going to prison. How did Lucky Devils come together?

I traced today’s sharps back to Vegas around 1980, when cheap computing met probability obsessives, even converging at a 1981 Tahoe summit on blackjack. The book shows how that culture forged the top tier.

What separates the true elites?

They’re math-first pragmatists who execute in real markets and stay emotionally flat, judging themselves over ten thousand bets, not one. It’s icy discipline married to applied statistics.

That’s the job: never too high, never too low, already on to next week. And almost no pro wants to talk, because there’s no upside in giving away an edge.

My guys begged me not to write it, but persistence and their late-career comfort helped, and I aimed at the making of them, not their code. Think learning from Michael Jordan’s mindset, not copying his jumper.

Why were you drawn to this beat?

I love uncovering the backstage, and gambling hides an entire layer where people prove you can win with math and grit. The leap-of-faith mindset—quit, move, lose for years, keep going—hooked me.

Was one character the spark, or the bigger pattern?

I wanted the spectrum of advantage play—roulette, poker, sports, horses—because if a game exists, someone’s engineering an angle. The method travels across formats.

Which game speaks to you personally?

Roulette—there’s a simple beauty to it, and back in Vegas I’d shove the bankroll on black and live with it.

What story do readers latch onto, and what’s your favorite?

Readers love Benter’s improbable rise and philanthropy, but I adore the Caesars biased-wheel hit where a team pounded the same cluster for nearly a day and walked with roughly three million. It’s wild that edge still exists.

When you spot an edge, you sprint; Simon, how long have yours lasted?

We crushed early NFL overs when college spread concepts hit, and again during fanless COVID before flipping to unders when books overcorrected. Now AI lets pros trigger automated line moves and feast on the reactions.

Pros say AI mostly boosts efficiency; what’s different in your world?

It speeds the grind and also automates tactics that get accounts flagged or banned, which is part of the dirty reality.

Even Benter’s in an AI phase, feeding decades of proprietary data into models that surface patterns he can’t always explain. The next arms race is bettors versus bookmakers’ AI.

Will you keep chasing AI angles in betting?

I poured the big lessons into the book and hope others run with massive lottery-syndicate stories—armies buying every combo, sometimes still losing. That world is ripe for a deep dive.

Think of Jelko and the Texas lottery scheme that forced rule changes; it’s the same cold-eyed math your book captures.

Someone should make the lottery-syndicate movie that shows the years of grind, not a one-night miracle.

Edges pop up in 50–50 raffles too, and the best hunters target low-attendance venues while spotting tiny patterns most people miss.

Big thanks to Kit Shilal—Lucky Devils is a perfect read while we wait for football. Watch on YouTube, rate and review, and as always, feedback is a gift—love you.