Winners & Losers: Bet Against the Dumbest Guy You Know

Why Trust Techopedia Gambling
Why Trust Techopedia Gambling

two gamblers laughing at a poker table

If you are anything like me, when planning to place a bet, you seek out the sharpest guy you know and follow his lead.

My friend David Paredes, who ranks among the smartest gamblers around (so much so that he helped to blow the lid off the UltimateBet.com insider-cheating scandal in 2008), won a tidy bundle by betting on Jake Paul to beat Mike Tyson last Friday night.

He’s not even a boxing expert, in fact, he is an extremely astute poker player. But he landed on the right side of the wager by going counter to the gambling plan of the least sharp person he knows.

Ask the Dumbest Guy You Know

mike tyson vs jake paul
Image: Julio Cortez / AP

Doing the opposite of following his North Star, Paredes made nearly $17,000 worth of wagers on the likelihood of this guy being wrong.

Certain people are just destined to lose,” Paredes told me a couple of days after the fight. “He’s your friend who, no matter what he does, is always on the wrong side. In poker, we call a guy like that a mush. I was looking for the biggest boxing mush.”

Paredes found his man: a habitual stoner, a friend of a friend, who seemed to be a full-time bumbler.

“When I asked who he was betting on, he told me it was Tyson,” recalled Paredes. “At that point, I knew Jake Paul was a lock.”

mike tyson vs jake paul
Image: Christian Petersen

This works best when you are dealing with a proposition on which people feel embarrassed about being on the wrong end of history.

After all, who wanted to lose money by betting against Iron Mike Tyson, even as he was within jabbing distance of being a senior citizen and boxing against a kid in his 20s?

Presidential Embarrassment

The recent US Presidential election was a similar case. While many voters were loath to admit that they’d cast ballots for Donald Trump and feigned being Kamala Harris supporters, so many did vote for Trump and so many bet on him to win.

There was a French gambler who understood this phenomenon perfectly. He took a major position on Trump, which was confirmed by asking people who their neighbors were voting for. Trump came up way more often than Harris.

The Frenchman ended up winning $49 million. Not only did the mystery trader predict a Trump win, but also wagered on Trump’s success in both the popular vote and several key swing states.

Classic Advantage Play

Of course, in the case of the fight, everybody said that they wanted Tyson to win – “I wanted Tyson to win,” Paredes told me. “I grew up watching him” – but Paredes realized where the smart money was going.

And he saw holes in the set-up for the match. “There were a lot of weird rule things, like the shorter rounds and the heavier gloves,” Paredes said. “They all worked in Tyson’s favor.”

Giving Tyson a helping hand did not augur well. Those special rules deployed to make the fight closer, according to Paredes, “were another indicator that Tyson wasn’t going to win.”

Plus, the mentality of the public, was clearly on the side of Tyson. All of that just made it very clear that I should bet on Paul. In my opinion, the line should have been much heavier than it was [in terms of Paul being a favorite to win].”

My Tyson vs Paul Bet

In the interest of full disclosure, I wanted to bet on the fight. But I couldn’t get my sports-wagering app to find Tyson vs. Paul. (I know… It was a little weird; I need to sign up to one of the best online sportsbooks.

As a result, I didn’t get put down any money. If I had, though, sadly, it would have been a couple of hundred on Tyson. And I would have been a first-class mush on this one.

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Michael Kaplan
Gambling Author and Journalist
Michael Kaplan
Gambling Author and Journalist

Michael Kaplan is a journalist based in New York City joined Techopedia in November 2023. He is the author of five books ("The Advantage Players" comes out in 2024) and has worked for publications that include Wired, GQ and the New York Post. He has written extensively on technology, gambling and business — with a particular interest in spots where all three intersect. His article on Kelly "Baccarat Machine" Sun and Phil Ivey is in development as a feature film.