Similar to Floyd Mayweather, Curtis ‘50 Cent’ Jackson is another example of someone who loves to flaunt his betting activities on social media.

The famous rapper has placed some huge bets in his time, which we will outline later, but contrary to Money Mayweather, he doesn’t mind highlighting the darker side of gambling.

Not only has ‘Fiddy’ written lyrics such as, “I got a gambling problem” and “I lost money when I bet on Roy,” he also spoke about it in 2006.

"I gamble too much, I gamble for too much money and it's something I have to address,” he said.

“I've got to realise no matter how much I win, it ain't a lot—it's only a lot when I lose. And you always lose. I think it's fun, I think it's exciting. I'm gonna continue to do it but I have to get to a point where I don't try to break the casino, 'cause you never can."

Even though he’s open about the dangers of gambling, Jackson has made some serious money from sports betting, here are some of his biggest bets.

BACKING THE NEW YORK GIANTS DURING THEIR SUPER BOWL 46 CAMPAIGN

In 2012, 50 Cent placed a series of bets that would be his claim to fame in the sports betting world.

He bet that the New York Giants would beat the San Francisco 49ers in the NFC Final, making a juicy profit of $500,000, which he would give to his grandmother!

Jackson claimed that he placed the bet due to the “voice in his head”, but hold on, there’s more craziness to come.

‘Fiddy’ then decided to go double or nothing, placing a whopping $1 million on the Giants to win the Super Bowl over the undefeated Patriots.

And the voices in his head prevailed once again, cashing in on his very brave wager.

THE SIDE BET WITH BIRDMAN THAT HE SHOULD’VE TAKEN

Funny enough, fellow rapper Birdman, who we wrote here, offered to bet against 50 Cent in the same game, but with a bigger stake.

He wanted to bet $5 million, to which Jackson turned down! I wonder how much he regretted that!

But overall, ‘Fiddy’ walked away from those two New York Giants fixtures with just a few more million dollars!

HIS HILARIOUS OFFER TO FLOYD MAYWEATHER

For those who don’t know, there is a running joke in the Boxing world, bet it true or false, that boxer Floyd Mayweather, who we wrote about in our previous article, is illiterate and can’t read.

With this in mind, Jackson challenged Floyd to read one page of a Harry Potter book without stuttering, and if successful, he would donate $750,000 to a charity of Mayweather’s choice!

Although it’s not sport betting related, it’s pretty damn funny!

In typical Mayweather fashion, Floyd responded to 50 Cent’s challenge with a few photos of 8-figure cheques, so maybe his maths is a bit better!

BETTING ON BOXING

His offensive offer towards Mayweather hasn’t stopped him betting on the undefeated fighter though, saying he would bet $1.6 million on Floyd to beat Manny Pacquiao, in what was the biggest boxing fight of all time.

If his words were true, he would’ve cashed in big time on that one!

He also successfully bet on Floyd to beat Oscar De La Hoya in 2007.

NOT PAYING UP TO WEBBIE?

In another boxing bet, it was said that Jackson made a bet with fellow rapper, ‘Webbie’, that Yuriorkis Gamboa would beat Terence Crawford, whilst Webbie was walking out to the ring.

According to Webbie, the pair agreed on a sum of $1 million, and when Crawford won, ‘Fiddy’ refused to pay up.

50 Cent’s management denied the rumours that a bet was agreed on between the pair, which is believable considering the size and spontaneity of the bet, and also the fact that Jackson was there managing Gamboa.

Check out the other articles in our 10 Celebrities and Sportsmen Who Are Sports Bettors series on:

• Article 1: Michael Jordan, the ultimate example of NOT having a betting strategy
• Article 2: Ashton Kutcher, the 'dumb actor' who placed bets for the largest sports betting syndicate in America
• Article 3: Floyd Mayweather, successful sports bettor or more trash talk?
• Article 5: Pete Rose, the illegal gambler who cost himself $100 million
• Article 6: Charlie Sheen, so addicted to gambling that he didn’t even care when he won a million dollar bet
• Article 7: Wayne Rooney, football legend and betting hypocrite
• Article 8: Bryan ‘Birdman’ Williams, another celebrity lacking a winning sports betting strategy
• Article 9: Charles Barkely’s horrible gambling philosophy, ‘lose hundreds of thousands, not millions’
• Article 10: Ben Affleck, the movie star who learnt how to count cards

Want to read about some other professional sports bettors or some of our customers who are on their way to becoming professional sports bettors too? Take a look at some of these videos/articles:

1. My Value Betting Journey from 1k to 2k
2. 10 People Who Got Rich From Sports Betting
3. Jonas Gjelstad Documentary Series - from $10k to $1m