Celebrities Who Won (and Lost) Big Betting on the Super Bowl

Betting on the Super Bowl is a huge business. Every year, Nevada registers hundreds of millions in wagers made on the annual game. Among the biggest wagers are made by celebrities and they have won and lost big betting on the Super Bowl.

Take a look at some of the biggest bets ever made and who hit big or lost it all (just wait till you see who made No. 1 with the biggest bet).

7. Phil Mickelson — $20,000

PGA champ Phil Mickelson made bank in 2001. | Jamie Squire/Getty Images

When it comes to this list, $20,000 doesn’t seem like a big number. But when a group Phil Mickelson was apart of took out a bet on the Baltimore Ravens winning the Super Bowl in 2001, the odds were 28-1. When The Ravens won, that group won $560,000. As an added bonus, they also bet on the long shot MLB World Series Champions, the Arizona Diamondbacks with odds of 38-1.

Next: This big bet is still a mystery.

6. Mystery person — $500,000

cityscape Las Vegas.
Rumor has it that a certain Fresh Prince made bank on the Super Bowl. | Sky_Sajjaphot/iStock/Getty Images

Someone bet $500,000 at South Points Sports Book and bet multimillions of dollars at the MGM Sports Book in Las Vegas for the 2018 Super Bowl between the Patriots and the Eagles. The bets were made for the Eagles to defeat the Patriots. Since this bettor cannot be identified, we put them at the bottom of the list.

There are rumors that it was either the same guy who took Las Vegas for millions of dollars in the world series or the Fresh Prince himself, Will Smith. Since we can’t identify the person who made the bet that won millions upon millions of dollars, we have to put this one on the bottom of the list.

Next: Mr. Cash-Money proves he’s got it.

5. Birdman — $1 million

Birdman won big in 2011. | Matt Winkelmeyer/Getty Images for BET

When it comes to audacious spending, no one does it better than a rapper. In 2011, Hip Hop artist and Cash-Money co-founder Birdman placed a $1 million bet on the Green Bay Packers winning the Super Bowl. The Packers ended up beating the Steelers that year, but the only evidence that Birdman won anything was that he tweeted “Just cashed in a milli.”

Next: Why stop at just one big win?

4. Birdman (again) — $1 million

Birdman wasn’t as lucky the second time around. | Matt Winkelmeyer/Getty Images for BET

After “winning” big the previous year, Birdman wanted to bet $5 million against anyone who would take him up on the challenge. Fellow rapper 50 Cent answered the call, but only for a cool million. Birdman put his money on the Patriots in the 2012 Super Bowl. Unfortunately for him, the Giants came out on top.


Next: A Las Vegas legend puts down an unheard of bet for his time.

3. Bob Stupak — $ 1 million

Stupak was a Vegas high-roller in his day. | Pascal Le Segretain/Getty Images

If you are unfamiliar with who Bob Stupak is, he was a Las Vegas impresario who was known for his huge publicity stunts and his eccentric vision for the future of Las Vegas. In 1989, he made a gigantic bet on the San Francisco 49ers winning the Super Bowl. That size of a bet would be the equivalent of over $2 million in today’s money. That bet paid off because the Niners were able to defeat the Bengals in a nail-biter victory, 20-16.

Next: This WSOP champion learns that he should have stuck to poker.

2. Phil Ivey — $2 million

The poker champ lost $2 million on the Colts. | Simon Fergusson/Getty Images

When it comes to large bets, this man is no stranger. Phil Ivey has won the World Series of Poker at least 10 times and has been to dozens of final tables. In 2010, Ivey placed a $2 million dollar bet that the Colts would beat the Saints in the Super Bowl. Unfortunately for Ivey, the Colts lost to the Saints, 31-17.

Next: The agony of defeat doesn’t hurt as bad when you deny it ever happened.

1. Floyd Mayweather – $10 million

Floyd Mayweather Jr
Mayweather reportedly lost $10 million on the 2013 Super Bowl| Ethan Miller/Getty Images

Allegedly, Floyd Mayweather placed a $10 million dollar bet on the Broncos to win the Super Bowl in 2013. The Broncos lost that year to the Seattle Seahawks.  Mayweather denies that he ever made the bet, but that’s probably because of the embarrassment of losing that much money. Mayweather is known for making large sports bets and even tried to bet $400,000 on himself.