Top 10 Bets in Sports History

Floyd “Money” Mayweather has a lot of, well, money. His net worth is roughly $180 million USD. So when Mayweather reportedly put down just over $10 million on the Denver Broncos beating the Seattle Seahawks in this year’s Super Bowl, no one was all that surprised. While Mayweather has since denied he put any money on any of the Super Bowl teams, it did prompt the question, “What are the best sports bets in history?” And with rumours of Mark Cuban (billionaire owner of the Dallas Mavericks) cashing in $20 million on a safety being the first play of the game (also not true), I couldn’t resist making this week’s top 10 sports bet related.

10. Curtis Jackson III (50 cent)

Prior to the 2011 Super Bowl, I really wish 50 Cent filled us in on Eli Manning being one of the most clutch playoff quarterbacks in the NFL. Jackson bet $500,000 on the Giants in the NFC Championship game and another $1 million on the Giants in the Super Bowl – as if he needed the extra cash flow.

9. Cardinals at 999:1

The St. Louis Cardinals were five games out of a Wild Card spot with only 15 games left to play. For one anonymous Cards fan, this seemed like the perfect time to ignite money into flames. The odds for the Cardinals to make the World Series was an astonishing 500:1, and to win the World Series, a measly 999:1. Well folks, the Cardinals beat the Texas Rangers in seven games and the unnamed gentleman cashed in a whopping $375,000.

8. Betting the ponies

I don’t bet, and to be honest, gambling seems like a senseless waste of money to me. But bring me to Woodbine Racetrack and put me near the middle-aged Caribbean men screaming at horses in slang I can’t make sense of, and I’m betting whatever is in my chequing account that day. Compulsive gambler Darren Yates put down £67.58 (roughly $100) on jockey Frankie Dettori to win all seven races he was jockeying in that day. As incredibly Hollywood-esque as this seems, Yates won that bet and it earned him an incredible £550,823 (over $860,000 USD).

7. Dime a dozen

In horse racing, the superfecta is the Holy Grail and the Royal Flush of the sport. To hit it, you must predict the top-four horses in one race, in exact order. Two off-site bettors placed a whole dime on the superfecta and, as unlikely as it is to even see one person win a superfecta, they both won. To do so they had to bet on Slambino, the horse with 88:1 odds to win.

6. 1,666,666:1

The next time you have 30 British pence (about 50 cents) lying in your couch, go out and place an accumulator bet on the Champions League that can appreciate 15 fold. Mick Gibbs did exactly that when he correctly guessed the winners for all 15 Champions League soccer matches he bet on. The odds were stacked against him at 1,666,666:1, and he clearly wasn’t put off by the reoccurring triple sixes. Bayern Munich won the trophy that year, but Gibbs was the real winner here, bringing home £500,000 ($784,000 USD).

5. In Lewis we trust

When you take your siblings or cousins to the Go-Karting track at 13, do you ever sit there and think; “This kid’s got something”? An anonymous man did, and he bet £100 that Lewis Hamilton would lift an FI World Championship before he was 25. Hamilton did, and the man won £10,000.

4. Mr. Las Vegas

I’m not too sure what possesses a bookie to place a bet with a man whose nickname is “Mr. Las Vegas,” but in 1989, someone took Bob Stupak’s bet. The elderly man, looking a lot like Hunter S. Thompson in Fear and Loathing, placed a flat million on the Bengals beating the seven-point favourites, the 49ers. PLOT TWIST! Stupak lost the bet, but anyone that has his nickname and style deserves to make the list.

3. Charles Barkley

Barkley is the antithesis on how to bet smart. He’s lost well over $10 million at casinos, and that’s just what’s been reported. But Barkley clearly foresaw the evil empirical dynasty that is the New England Patriots. The Pats were 14-point underdogs heading into Super Bowl XXXVI against the St. Louis Rams and the “Greatest show on turf.” The Pats won and so did Barkley who bet $550,000.

2. No Mula baby

Birdman put a staggering $2 million on the Miami Heat to beat the Dallas Mavericks in the 2011 NBA finals. While the Maybach driving rap star was sitting pretty with the Heat up 2-1 in the series, Dirk Nowitzki and company turned it up to 11 and they went on to win the Championship 4-2. Birdman was seen with Lil’ Wayne later that night partying with the Mavericks. Seriously.

1. Pete Rose

This was a no-brainer! There will never be another sports betting scandal in North America that matches the fanfare, controversy, and antagonism that Pete Rose produced betting $2,000 to $10,000 every night on his own Cincinnati Reds…to win! Rose was barred from MLB in 1989 and, despite putting up Hall of Fame numbers, will likely never be nominated to the Hall.