Colin Cowherd Podcast - Insane Sports Gambling Stories on Mike Tyson, Mickelson, Ohtani, Mayweather, The Mob

I just tore through The Bookie on a flight from Naples to Chicago, and it’s a blast—gangsters, celebrities, the whole high‑stakes sports betting world—with proceeds going to World Wildlife Fund and Blood Cancer United. I met Art Manteris back when I was living in Las Vegas, practically camping out at the Hilton sportsbook on weekends, and I even introduced him to his wife; so, Art, take us back to Caesars asking you to bring order to a chaotic sportsbook.

In 1980 the books were loose on rules and light on procedures, and it showed. I made compliance the top priority, guest service second, revenue third, and once finance and audit saw we wanted a clean, regulated operation, they backed the overhaul.

You and Chuck Esposito were the guys I trusted, but sharps like Billy Walters and Lem Banker didn’t exactly play nice; how did you handle that push‑pull?

I respected their talent, but they were opponents, not partners. My job was to protect the license and the bottom line, so friction with players who threatened either was inevitable.

Explain runners—people placing bets for whales—and the cat‑and‑mouse of spotting them.

Nevada bans messenger betting, and New Jersey now restricts similar proxy play, but proving it is tough. If lines move across the market the instant a guy is betting with you, that’s a tell; I’d rather err on caution than leniency.

You’ve got a wild Earl Strom story—gamblers tracked an NBA ref to find edges on totals before the internet.

A very sharp bettor literally followed Strom city to city because he believed Strom’s tendencies swayed totals, and he wagered accordingly.

Boxing put you around sensitive info; during Mayweather–Pacquiao you hit an ethical wall—what happened?

I learned before the fight that Pacquiao was hurt and couldn’t win, and it cemented my belief that promotion and betting must stay separate; I preached that later while consulting for the NBA. What shocks me now is how fast leagues embraced gambling partnerships, a mixed message that Europe is already pushing back on.

On Tim Donaghy, I’ve long argued Vegas is the leagues’ ally—were you blindsided?

We didn’t see unusual money on those games, unlike the Arizona State point‑shaving mess we nailed in the nineties, and I regret missing it. Prop bets and in‑play are fun, but props on college athletes invite trouble; the industry should drop those.

Let’s revisit Tyson–Buster Douglas; I called it the safest bet ever—what was it like on your side when a massive upset hit?

I passed on booking it because the price felt like a non‑contest, and the public still piled on Tyson at something like twenty seven to one. Later we learned Douglas fought inspired and Tyson wasn’t himself, which explains how that shocker happened.

After the Supreme Court opened the floodgates and apps took over, how did that change Vegas?

Vegas books remain strong, though this year’s Super Bowl handle dipped for several reasons, including a less star‑driven matchup and more people betting at home. The city has to compete smarter now—things like parking fees and add‑ons matter.

What share of your room was sharps versus squares back at the Hilton?

Most bettors live in the middle, and today’s data makes everyone sharper than in the newspaper‑chasing days. Many believe their opinion beats the market; a few do over time, most don’t.

I hit fifty nine and a half percent this NFL season, but margins are thin—how do you see the marketing blitz with leagues?

Sportsbooks run on slim edges with heavy tech and staffing costs, so splurging on league tie‑ins rarely pencils out. If someone wants to bet, they know where to find us without ads every timeout.

Golfers often love action; when did Phil Mickelson land on your radar as a bettor?

He was a regular in the late nineties, generally an average bettor who wagered bigger because he could, and he treated our staff well. He later got in too deep, made restitution, and stopped; I respect that.

Which sports quietly give operators fits—hockey comes to mind.

Hockey was a sharp’s playground until the Golden Knights arrived and the public flooded in, which created big swings and our biggest sweat that first year. Football still rules, March Madness is massive, and baseball is lighter per game but adds up through volume.

I remember Ivy League syndicates carving up small conferences; did you change limits there?

A study proved we barely made money on small leagues while major conferences paid the bills, so we raised limits on the power games and kept the small stuff tight. Sharps hated it because niche leagues were their best edges.

When the Ohtani interpreter story broke, what was your first read?

I knew the alleged bookmaker as a big player without visible income, which raised flags, but I have no inside facts on this case. The larger point stands: integrity is everything, and leagues moved too far, too fast into betting partnerships.

Back in the day, did the mob’s presence ever put you in a tight spot?

I dealt with a runner who tried to dictate prices, and as a young writer I once miscounted by eleven hundred dollars until Jimmy Vaccaro quietly covered it, which taught me who to follow. A Spilotro associate later floated a ‘we can help each other’ pitch I brushed off, and by the mid‑eighties that influence was fading.

Art, the book is a joy for anyone who loves the behind‑the‑ropes stuff; do you still get the itch to bet a game?

No—boxing and the tennis majors still tempt me, but I stay out of the pools. And Colin, it’s been great watching your rise; not surprising to me at all.