Hall Of Fame Bookmaker Shares Crazy Gambling Stories About Mob, Tyson, Mickelson On Colin Cowherd Podcast

In case three hours of FS1’s The Herd isn’t enough to satisfy your craving for sports takes, Colin Cowherd has a podcast, too, where he usually does longer interviews with fascinating guests. Recently, Cowherd sat down with a true legend of sports betting, former Westgate SuperBook director Art Manteris, to reminisce about the golden era of Las Vegas. 

From the days of backroom handshakes to the modern corporate takeover, Manteris tells stories from his new memoir, "The Bookie: How I Bet It All on Sports Gambling and Watched an Industry Explode." In this sit-down, he dishes on the "whales" like Phil Mickelson and Floyd Mayweather, and the night Mike Tyson’s loss to Buster Douglas nearly bankrupted his casino. 

Whale Plays: Mickelson’s Millions And Mayweather’s Duffel Bags

Allegedly, Phil Mickelson is an all-time degenerate. Biographers estimate Mickelson has lost north of $100 million gambling, and Manteris confirmed that in the Vegas reality, Phil was a "pure gambler." He wasn’t just looking for an edge; he lived for the adrenaline of the volume. For Mickelson, "the action is the juice."

Then, Manteris told stories of Mayweather walking into casinos with literal duffel bags of cash. But, while Phil was chasing the thrill, Floyd’s strategy was dropping seven figures on a heavy favorite to collect a "guaranteed" return, aka Bridge Jumper Bets. Essentially, Mayweather treats sportsbooks like a high-interest savings account with better security.

The Night The House Collapsed: The Tyson-Douglas Disaster

Every bookmaker has a "Black Swan" event. For Manteris, it was February 11, 1990, when Buster Douglas upset Mike Tyson in Tokyo. Most sportsbooks didn't even want to take action on Tyson vs. Douglas. However, Manteris, being the legendary he is, took the risk, opening Tyson at -2700. Iron Mike ended up closing as a -4200 favorite. 

In his prime, no one bet against Tyson. Yet, one sharp bettor dropped $54,000 on Douglas at 37-to-1 and hit Manteris's sportsbook harder than Douglas hit Tyson. When Iron Mike's mouthpiece hit the canvas, that bettor walked out of the Hilton with a cool $1.5 million. Much like Tyson, Manteris will forever be haunted by Douglas's win. 

Algorithms Ended Old-School Vegas Wiseguy Era 

Most of us are facing a reckoning when it comes to AI replacing our jobs. But Las Vegas has already dealt with computers replacing humans. Manteris discussed how Sin City transitioned from the "Mob" era to the corporate era. Back in his day, credit lines and disputes were handled with a handshake and a conversation in a back room.

I heard something similar the first time I visited Las Vegas back in 2009. I was hanging out at an empty poker table with the dealer, waiting for the game to fill, when, randomly, he started talking about how the corporations ruined Las Vegas, and it was much better when the Mob ran the city. 

Today, the "characters" have been replaced by algorithms. While the industry is now safer and more regulated, Manteris argues that it has lost its "feel." Corporations running today's apps don't care about bettors; they care about profits. But you've already heard this if you saw "Casino."

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