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Top Ten Biggest Won Sports Bets of All Time

Sports betting offers a mix of calculated strategy and the thrill of a gamble. It’s a realm where legends are made, proving that sometimes extraordinary risk-taking leads to spectacular wins. Let’s delve into ten of the most astounding sports betting triumphs in history:

1. Jim “Mattress Mack” McIngvale – $75 Million

  • Who: Jim “Mattress Mack” McIngvale, a Texas furniture store owner renowned for his energetic commercials and outlandish promotions.
  • How: McIngvale placed a series of bets on the Houston Astros to win the 2022 World Series, totaling a whopping $10 million.
  • Amount Won: When the Astros clinched the title, McIngvale took home a staggering $75 million, the most significant payout in sports betting history.
  • Interesting Notes: McIngvale used his bets as a hedge against furniture store promotions, promising to refund customers if the Astros won.

2. Tiger Woods $85,000 Masters Bet

  • Who: James Adducci, a novice sports bettor.
  • How: Adducci placed an $85,000 bet on Tiger Woods to win the 2019 Masters Tournament at William Hill sportsbook with 14/1 odds.
  • Amount Won: $1.2 million. This win set a record for William Hill’s most extensive payout on a futures bet.
  • Interesting Notes: Adducci needed his wife’s permission for the bet and it was reportedly his first sports wager ever.

3. “Vegas Dave” Kansas City Royals Future

  • Who: “Vegas Dave” (Dave Oancea), a well-known sports bettor.
  • How: Oancea bet on the Kansas City Royals to win the World Series when they had 30/1 odds. He faced difficulty finding sportsbooks to take his full wager and ultimately spread his bets across 15 casinos.
  • Amount Won: $2.5 million.
  • Interesting Notes: His persistence and belief in a long-shot team paid off in a major way.

4. Leicester City Premier League Future

  • Who: Multiple bettors across the UK, including several regular fans who placed wagers at the beginning of the season.
  • How: At the start of the 2015-16 Premier League season, Leicester City was considered a massive underdog with 5000/1 odds to win the title.
  • Amounts Won: Payouts varied, but several bettors won substantial sums, including one who cashed out early for over $100,000.
  • Interesting Notes: One of the most remarkable upsets in sports history, highlighting how even small wagers with long odds have huge potential.

5. 15-Leg NFL Parlay

  • Who: An anonymous bettor in Las Vegas.
  • How: Placed a $5 parlay bet on 15 NFL games, requiring every single selection to be correct to win.
  • Amount Won: A staggering $100,000.
  • Interesting Notes: The sheer level of difficulty and improbability of a 15-leg parlay makes this a jaw-dropping sports betting win.

6. “Vegas Dave” Holly Holm vs Ronda Rousey

  • Who: “Vegas Dave” (Dave Oancea).
  • How: Bet $200,000 on Holly Holm, a significant underdog, to defeat Ronda Rousey in a UFC fight.
  • Amount Won: $560,000.
  • Interesting Notes: Oancea scored a major upset by backing Holm, whose knockout of Rousey proved a massive turning point in UFC history.

7. Billy Walters New Orleans Saints $3.5 Million Bet

  • Who: Billy Walters, a highly successful and somewhat controversial professional gambler.
  • How: Walters placed a $3.5 million bet on the New Orleans Saints to win Super Bowl XLIV.
  • Amount Won: An estimated $3.5 million (Walters was notoriously secretive about his wins).
  • Interesting Notes: Known for his meticulous research and ability to spot betting value, Walters is considered one of the most skilled sports bettors ever.
  1. Phil Mickelson Baltimore Ravens Future
  • Who: Phil Mickelson, a legendary professional golfer.
  • How: In 2001, Mickelson bet $20,000 on the Baltimore Ravens to win the Super Bowl with 22/1 odds.
  • Amount Won: $560,000.
  • Interesting Notes: Mickelson’s bet demonstrated his confidence in the Ravens’ underdog status, and his golfing profits found their way into a successful sports bet.
  1. Charles Barkley $800,000 Patriots Super Bowl Bet
  • Who: Charles Barkley, NBA legend and famous sports commentator.
  • How: Barkley placed an $800,000 bet on the New England Patriots to beat the Atlanta Falcons in Super Bowl LI. The Patriots were trailing significantly at halftime.
  • Amount Won: $800,000.
  • Interesting Notes: Barkley’s bet was a high-stakes show of support for the Patriots and a testament to their incredible comeback to win the game in overtime.
  1. Richard Hopkins Lewis Hamilton Futures
  • Who: Richard Hopkins, a British man who had a childhood connection with Lewis Hamilton.
  • How: Over several years, Hopkins placed a series of bets on Lewis Hamilton to win Formula One championships before he had even entered the sport. The odds were extremely long since Hamilton was still a young kart racer.
  • Amount Won: Estimated around £165,000 ($200,000+)
  • Interesting Notes: Hopkins’s belief in Hamilton’s potential, stemming from witnessing his talent firsthand, paid off massively decades later.

Above article according to Gemini, below article according to ChatGPT.

Sports betting has always been a thrilling endeavor, with the potential for enormous payouts. Over the years, there have been some truly monumental wins that have defied the odds. Here, we delve into the top ten biggest sports bets ever won, exploring the highlights, amounts won, and the stories behind these legendary bets.

1. Leicester City Premier League Victory (2015-2016)

  • Amount Won: Estimated at £2.5 million
  • Bet Placed By: Anonymous bettor
  • How Won: A bettor placed a £50 bet at 5000/1 odds on Leicester City to win the Premier League at the start of the season. Against all odds, Leicester City clinched the title, resulting in one of the biggest betting upsets in sports history.

2. Tiger Woods’ Masters Victory (2019)

  • Amount Won: $1.19 million
  • Bet Placed By: James Adducci
  • How Won: Adducci placed an $85,000 bet at 14/1 odds on Tiger Woods to win the 2019 Masters. Woods’ victory marked his first major win in 11 years, turning Adducci’s bold bet into a massive payday.

3. St. Louis Cardinals World Series Win (2011)

  • Amount Won: $375,000
  • Bet Placed By: Anonymous bettor
  • How Won: A bettor placed a $250 wager at 500/1 odds on the St. Louis Cardinals to win the World Series when they were 10.5 games out of a playoff spot in August. The Cardinals went on a miraculous run and won the World Series, resulting in a huge win for the bettor.

4. Super Bowl XLIX Safety Bet (2015)

  • Amount Won: $250,000
  • Bet Placed By: Jona Rechnitz
  • How Won: Rechnitz bet $500 at 500/1 odds that the first score of Super Bowl XLIX would be a safety. The game began with a safety, and Rechnitz won a quarter of a million dollars.

5. Kansas City Royals World Series Win (2015)

  • Amount Won: $2.5 million
  • Bet Placed By: Anonymous bettor
  • How Won: A bettor placed a $100,000 bet at 25/1 odds on the Kansas City Royals to win the World Series before the season started. The Royals went on to win the championship, resulting in a massive payout.

6. Floyd Mayweather’s Bet on Himself (2017)

  • Amount Won: Estimated at $200,000
  • Bet Placed By: Floyd Mayweather
  • How Won: Mayweather is known for betting on his own fights. Before his match against Conor McGregor, he reportedly placed a series of bets totaling $400,000 on himself to win. He won the fight and cashed in on his confidence.

7. New England Patriots Super Bowl LI Comeback (2017)

  • Amount Won: $100,000
  • Bet Placed By: Anonymous bettor
  • How Won: A bettor placed a $1,000 bet at 100/1 odds on the New England Patriots to come back and win Super Bowl LI when they were down 28-3 against the Atlanta Falcons. The Patriots staged an incredible comeback and won, resulting in a huge payday.

8. Phil Mickelson’s Masters Win (2010)

  • Amount Won: $1 million
  • Bet Placed By: Billy Walters
  • How Won: Famous gambler Billy Walters bet $50,000 at 20/1 odds on Phil Mickelson to win the 2010 Masters. Mickelson’s victory earned Walters a cool million.

9. Nick Foles Super Bowl MVP (2018)

  • Amount Won: $100,000
  • Bet Placed By: Anonymous bettor
  • How Won: A bettor placed a $1,000 bet at 100/1 odds on Nick Foles to win the Super Bowl MVP. Foles led the Philadelphia Eagles to victory and was named MVP, resulting in a significant win for the bettor.

10. Rory McIlroy’s First Major Win (2011)

  • Amount Won: £100,000
  • Bet Placed By: Gerry McIlroy and friends
  • How Won: Rory McIlroy’s father and three friends placed a £400 bet at 250/1 odds when McIlroy was 15 that he would win a major before he turned 26. McIlroy won the 2011 U.S. Open, securing the bet.

These incredible wins showcase the unpredictability and excitement of sports betting, with each bettor taking a leap of faith that led to extraordinary payouts.

EDITOR’S NOTE: We are pretty sure that in this case, AI is far off the mark, and there are many other bigger bets out there, bigger than most of these. Let us know in the comments what you think or may know…

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