With some form of sports wagering now legal in over half the country, the interest in betting has never been higher. States where online betting is live have reported billions of dollars of sports betting handle. It seems that demand in the US for legal betting apps was bigger than anyone could have imagined.
What is the ultimate dream of every sports bettor? From the recreational player to the high roller, the hope is to hit that one big score. Of course, winning big might mean different things for different people. For some it’s spinning a small bet into a massive return. For others, it’s betting huge on a favorite team, athlete or event.
Let’s take a look at what are arguably the five greatest sports bets in history. And as we said, greatest doesn’t necessarily mean biggest. Spinning a a small investment into a huge payday is probably a more relatable dream for most casual betting fans.
1. Tiger Woods Wins the Masters – James Adducci Wins Big
The year was 2019. The scene was the 2019 Masters golf tournament at Augusta National Golf Course in Augusta, Georgia. As he had done almost every year since 1996, Tiger Woods had entered the Masters to win. He was still on a quest to win a fifth Green Jacket and add to his collection of 14 Majors.
The difference this time was noone else really thought he had much of a chance. His name was missing among the favorites to win the tournament. He was in a drought that saw him win only one tournament in the prior 5+ years and no Majors since 2008. He had been through personal turmoil and injury with multiple back surgeries under his belt.
Having lost faith, oddsmakers made him +1400 to win.
That number was a little too big to resist in the eyes of James Adducci. With permission from his wife, he took the bait and wagered a whopping $85,000 on Tiger Woods to win the Masters. Lightning struck, Woods got his 5th Green Jacket and James Adducci walked away with $1,190,000 in his bank account.
2. Female Sports Bettor Hits With 15-Leg NFL Parlay
At true odds of 32,768-1, it’s near impossible to hit a 15-Leg NFL Parlay. While there might not be any official data to support that contention, it’s a “good bet” that it has only happened four or five times through a legal bookmaker in the US. One of those occurrences took place in October of 2015.
Tayla Polia was your typical recreational sports bettor. Her bets were small and her dreams were big. When she wagered $5 on a 15-leg NFL parlay, she probably did so without much expectation. She was in for a surprise. All 15 legs came up trumps and she won a whopping $100,000 (20,000-1) on her $5 wager. The bet featured 9 favorites, 5 underdogs, and 1 over/under, all of which combined covered all 15 games on the NFL schedule for that week.
3. “Vegas Dave” Strikes It Big With the Kansas City Royals
In US sports betting circles, Dave Oancea (A.K.A. Vegas Dave) is known for two things. One, he is generally considered to be obnoxious. Two, the size of his sports bets is legendary.
In 2015, just one week into the MLB regular season, Vegas Dave had a strong premonition about the Kansas City Royals winning the World Series. At odds of 30-1, he swung for the fences with a wager of $140,000. The wager was big enough to intimidate Las Vegas Bookmakers who promptly took to spreading the amount of the wager among 15 different participating sportsbooks.
That was a smart move on the part of bookies as the Royals did win the 2015 World Series, a Series victory that made Vegas Dave a sports betting legend and put $2.5 million in his bank account in the process.
4. The Legend of Sir-Ride-A-Lot
The name of the sports bettor is not known to this very day. He came to Las Vegas from somewhere in Europe to stake his claim as one of the most astute and brave sports bettors of all time. That earned him the moniker “Sir-Ride-A-Lot.”
The year was 2017 and the event was the 2017 World Series between the Houston Astros (AL) and the Los Angeles Dodgers (NL). Yes, this is the very same World Series that was marred by the Astros’ sign-stealing scandal.
His initial large wager was on the Los Angeles Dodgers in Game 1, a game they won with a score of 3-1. He let his bet and winnings ride with a Game 2 wager on the Houston Astros, who won the game 7-6. In Game 3, everything was wagered on the Astros who won 5-3. He continued letting everything ride with a wager on the Dodgers in Game 4, a game the Dodgers won 6-2. By the time Game 5 rolled around, the amount of his wagers was getting up there. Still, he let it all ride on the Astros in Game 5, which they won 13-12 in one of the greatest World Series games ever.
After that winning bet on Game 5, his bankroll had swollen to $6 million. He took one more shot with a “money line” wager on the Dodgers to win Game 6. With a final score of 3-1, the Dodgers covered the run line and our mysterious sports bettor had a bankroll of $14 million. Finally siding with caution, he chose to cash out and take his winnings to the bank.
For the record, several Las Vegas bookmakers shared in the beating. Also for the record, he apparently would have bet on the Dodgers in Game 7, a loser.
5. Floyd Mayweather Scores With Miami Heat Wager
Boxing great Floyd Mayweather is known for more than just his prowess in the boxing ring. He also has a reputation as a “high roller” in sports betting circles. There are claims that his gross winnings over the years exceed $1.0 billion.
In 2013, the Miami Heat were favorites to beat the Indiana Pacers in an NBA playoff game. He promptly wagered $5.9 million on the Heat, who crushed the Pacers by 23 points behind the efforts of Lebron James.
Mayweather banked $5 million for the win in what is currently regarded as the largest single game wager in history on an NBA game.