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Mattress Mack and the Top Ten Most Outrageous Betting Wins in United States History

Mattress Mack laughed all the way to the bank this week, taking an incredible $75 million from a variety of sportsbooks when the Houston Astros won the World Series.

Mack, whose full name is Jim McIngvale, is a furniture store owner in Texas and may be the most famous high-risk gambler in the United States.

But he’s also far from the only big fish taking swings at major paydays. Compare.bet analyzed some of history’s most outrageous sports betting wins and ranked the top-10 most unforgettable whoppers.

10. Lefty Gets it Right

Phil Mickelson is known for his golf exploits but he is also an avid gambler. It’s gotten him in trouble, but he’s also hit on some big bets. Lefty’s best call may have been a +2200 wager on the Baltimore Ravens to win the Super Bowl back in 2000.

Mickelson wagered $20,000, and once Baltimore hoisted the Lombardi Trophy at the end of the year, he pocketed a cool $560,000. 

9. Bettor X Marks The Spot

The media called this anonymous person Bettor X, and indeed they found the right spots to strike gold. Bettor X started off their incredible run during the 2017 World Series between the Los Angeles Dodgers and Houston Astros, hitting on a series of bets that amassed more than $10 million.

After that, the attention was turned to the Super Bowl, where once again Bettor X was highly profitable by placing between $8 and $10 million on the underdog Eagles against the Patriots. Philadelphia won, wrapping up one of the most lucrative runs in sports betting annals.

8. Vegas Dave’s Royal Win

The Kansas City Royals were 30/1 longshots to win the 2015 World Series, but that didn’t deter Dave Oancea from betting nearly $100,000 on them to win it all. ‘Vegas’ Dave had to spread the wager out over multiple sportsbooks because many didn’t want to take on the liability.

Once he collected from the various spots, Vegas Dave ended up with a cool $2.5 million.

7. Money Mayweather Cashes In

Even though he would be loathe to admit it, boxing legend Floyd Mayweather, Jr. has reportedly lost a lot of money gambling over the years. But when the sums are so big, he’s naturally going to win some big ones.

Mayweather allegedly put down $5.9 million on the Miami Heat to cover the spread in Game 7 of the Eastern Conference Finals against the Indiana Pacers in 2013. The Heat covered, and if Mayweather truly bet that much, he profited more than $5 million.

6. The Money Comes Marching In 

Billy Walters is one of the most famous sports gamblers in the United States, and he was no stranger to wagering millions of dollars per year on sports. He went in big-time on Super Bowl XLIV between the Indianapolis Colts and New Orleans Saints.

Even though Peyton Manning and Indy were the favorites, Walters bet on New Orleans and came away with a whopping $3.5 million when the Saints won, 31-17.

5. Just Two Good

Tonya Polia had made exactly one prior sports wager before putting together a 15-leg parlay on NFL action. The chances of hitting were astronomical on her second lifetime bet, as was the potential payout.

Well, the Vikings covered, as did the Falcons, Texans, Chiefs, Redskins, Patriots, Cardinals, Giants, Sehawks, Packers, Chargers, Steelers, Bengals and Lions. Add in an over on the Steelers-Broncos game, and a dart throw of a $5 bet resulted in a $105,000 payout.

4. Million-Dollar Marco Rides the Parlay

Marco Piemonte is known for making, and winning, big-time wagers. And on Sept. 25, 2022 he put down $65,000 on a six-team parlay. After one push lowered the odds, Piemonte still had $2.9 million on the line when the Denver Broncos faced off against the San Francisco 49ers after four legs had hit.

The Broncos needed to cover as 2-point underdogs and ended up pulling out an 11-10 outright win after a late rally, earning Piemonte a seven-figure payout.

3. Free Bet Madness

FanDuel offered a $20 free bet to Jett Honig before last year’s NFC and AFC Championship games, and he went big with it. Honig chose exact scores for Chiefs-Bengals as well as Rams-49ers, and incredibly, they both hit.

The odds of Kansas City-Cincinnati finishing 27-24 Bengals was 220/1, and the odds of Los Angeles-San Francisco ending up 20-17 Rams was 130/1. Add them both together, and the incredible parlay netted Honig nearly $580,000.

2. First Time’s a Charm

James Adducci had never bet on a sporting event in his life until he put down $85,000 on Tiger Woods to win the Masters in 2019. This was far from prime Woods, so the odds sat at 14-to-1 for him to pull it off.

Well, Woods indeed won the prestigious tournament, which resulted in Adducci cashing in on a $1.2 million payout. Not a bad way to begin your sports betting experience.

1. Houston, We Have A Winner

Mattress Mack has long been known for placing astronomical bets, doing so to bring publicity to his business. He was a loser in the Super Bowl when the Bengals fell to the Rams this February, but rebounded in a big way in the Fall Classic.

Mack put about $10 million on Houston Astros futures to win the World Series. The money was spread out between books, and in one instance, he crossed the state line to Louisiana to place a wager at Subway because betting is not legal in Texas.

Houston trailed the Philadelphia Phillies 2-1 in the seven-game series but came roaring back to secure the championship, which rewarded Mattress Mack with the $75 million payment, believed to be the biggest in sports gambling history.

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