Despite historic loss, pro says betting $40K to win $1K pays off

Most people like to bet a little to win a lot. Longtime Las Vegas pro sports bettor Steve Fezzik often bets a lot to win a relative little.

That strategy backfired in historic fashion in last year’s NCAA Tournament, when Fezzik lost $80,000 in money-line wagers to win about $1,800 on heavily favored Purdue (-4,500) to beat Fairleigh Dickinson.

The Boilermakers, who were 23½-point favorites, became the second No. 1 seed to lose to a No. 16 seed when the Knights dealt them a shocking 63-58 defeat in the biggest point-spread upset in March Madness history.

I asked Fezzik this week about his thought process behind that bet and similar wagers.

“To be fair, I’ve done very well making bets like this through the years,” he said.

It’s a simple case of math for Fezzik, 60, a former actuary from Dayton, Ohio, who studied probability and statistics at Northwestern, where he earned a degree in industrial engineering.

NCAA basketball favorites of between 22 and 24½ points have won 449 of 454 games since 2006, according to boydbets.com, for a winning percentage of 98.9. That equates to a -9,090 money line, while a 98.0 win percentage equates to -4,999.

So Fezzik believes he has an edge when he can lay less than -5,000 in those games. He said he routinely lays -4,000 and will do so again in the NCAA Tournament.

“I bet $40,000 all the time to win $1,000. But it’s something you probably shouldn’t be doing unless you’re a guy with a documented track record and strong math history,” he said. “The real key number is when you get a favorite above 22 points and I can lay -4,000. That would be the sweet spot.”

Deja Purdue

He told me that Tuesday. As fate would have it, on Wednesday he posted on X that he was on Villanova -4,000 on the money line over DePaul in the Big East tournament.

Fezzik told me that he actually bet $38,000 to win $1,000 on the Wildcats, who were as high as 24½-point favorites over the Blue Demons, who went 0-20 in the conference in the regular season.

But it was deja Purdue all over again as DePaul led by eight in the second half and was up 57-55 in the final seconds. This time, Fezzik and Villanova escaped a massive upset when Justin Moore made a 3-pointer with eight seconds left to lift the Wildcats to a 58-57 win. The Blue Demons (3-29) ended their season on a 20-game losing streak.

“The insane thing is that this game I had the upmost confidence there was no way DePaul was good enough to win,” Fezzik said in a text message after the game. “Two close games against Georgetown, 18 blowout losses. Crazy.

“I actually loved this bet. I was regretting not getting more. Until about five minutes left in the game.”

Will Fezzik bet Purdue on the money line again in a No. 1-No. 16 matchup? He recently posted that question in a poll on X (@FezzikSports), where “Yes, 99% bets -4000 good” won over “No, he cannot be that dumb.”

“I’ll certainly go to the well with it again,” he said. “The key here is bankroll management.

“I should’ve done a better job of telling people don’t bet more than 5 percent of your bankroll. That’s a good rule of thumb for almost all bettors.”

Contest king, tout

Fezzik has won more than $1.5 million in prize money in handicapping contests since he left his job in Los Angeles as a vice president for Transamerica and moved to Las Vegas in 2001 to become a full-time pro sports bettor.

“I was making more per hour than my corporate job and having way more fun,” said Fezzik, whose real name is Steve Fenic.

The only back-to-back winner of the Westgate SuperContest (in 2008 and 2009), Fezzik was in contention in the Circa Sports Million contest last season before finishing 21st in a field of 5,274 with a 56-31-3 record against the spread (64.4 percent).

He also cashed in the Circa Survivor contest in which four winning entries split the $9.2 million prize for $2.3 million apiece. Fezzik bought 16 percent of Greg Jones’ entry, which equates to about $370,000, and Jones said he wouldn’t have won without his partner’s help.

Despite his success, Fezzik is a polarizing figure in sports betting, mostly because he sells his picks on pregame.com.

“There’s a feeling that 90 percent of these pick sellers lose and they’re ‘scamdicappers’ and they’re bad guys,” he said. “The truth is 90 percent of pick sellers do indeed lose. But the vast majority of the ones I’ve met are hard-working, diligent people.

“It’s not that they’re scamming anyone. It’s just really hard to win.”

Contact reporter Todd Dewey at tdewey@reviewjournal.com. Follow @tdewey33 on X.