Legendary Gamblers: 50 Cent

A man who has seen it all and is still standing, 50 Cent had a music career that skyrocketed him to the top of the industry, he starred in films, became a household name as a legend in rap, but he has also seen some large pitfalls.... One of his main pitfalls being declaring himself bankrupt after multiple law suits and gambling fails - so just how did he get there?

Who Is 50 Cent?

50 Cent, born Curtis James Jackson III in Queens, New York, is a legendary rapper, actor, entrepreneur, and gambler who rose to fame in the early 2000s. His debut studio album Get Rich or Die Tryin debuted at number one on the Billboard 200 with multiple songs on the album reaching number one on the Billboard Hot 100. In fact, many publications consider this album to be the best rap album of the 2000s!

Over the course of his career, 50 Cent has sold over 30 million albums worldwide and won many awards including a Grammy Award and a Primetime Emmy Award. Outside of music, 50 starred in his semi-autobiographical movie Get Rich or Die Tryin' as well as several other films throughout the 2000s. So it is safe to say that 50 would have a fair bit of dosh behind him, but gambling isn't always about the money...

What Makes 50 Cent’s Gambling So Legendary?

Beyond being a top rapper, actor, and entrepreneur, 50 Cent is also one of the most popular gamblers the world has known. Time and time again, 50 Cent found himself in the headlines by making high-stake wagers to put him in legendary status.

His Million Dollar Bets

Boxer, Floyd Mayweather has been at the center of many of his high wager bets, with 50 placing a million dollar bet for Mayweather to beat Oscar De La Hoya in 2007. He upped the ante in 2015 by wagering $1.6 million on Mayweather to beat Manny Pacquiao; he ended up winning both of these wagers by the way.

However, he hasn’t always wagered favorably to Mayweather. While people on social media were completing the Ice Bucket Challenge for charity, 50 Cent was challenging Mayweather to a different challenge. He placed a wager on Mayweather not being able to read. To prove this he wanted Mayweather to film himself reading one page from a Harry Potter book, and if he did, 50 would donate $750,000 to a charity of Mayweather's choice. When Mayweather didn’t take him up on the offer, 50 said that it could be The Cat in the Hat. Unfortunately, Mayweather never accepted the challenge.

Betting He Would Beat Kanye

Another unique wager of 50’s was against fellow rapper Kanye West, which had them squaring up against each other on September 11, 2007. Both were dropping albums on the same day with both expecting to be top sellers in the industry. Before the album release date, 50 said that his album Curtis would outsell Kanye’s album Graduation and he would not release another solo album if it did not. Graduation outsold Curtis 957,000 to 691,000. In the end, however, 50 did not stay true to his word and released two more solo albums after the wager.

The Million Dollar NFL Win

Away from boxing wagers, 50 has had great success wagering on the NFL at very high stakes. In 2012, the New York Giants beat the San Francisco 49ers in a playoff game. 50 had made a wager on the game, which netted him $500,000 in profit.

50 then decided to let his winnings ride on the New York Giants as they faced the New England Patriots in the Super Bowl. The Giants defeated the Patriots and 50 Cent became a million dollars richer, leading to one of the greatest runs a high-stakes gambler has seen during the NFL playoffs.

50 Cent’s Biggest Gambling Controversies

While 50 Cent has enjoyed many high-wagering wins in his betting career, he has also had to deal with a lot of losses, as well as controversy...

Filing For Bankruptcy in 2015

Despite all the wins, the rapper had to file for bankruptcy in 2015. 50 stated that back in 2010, his net worth was around $500 million but was closer to $30 million when he ultimately went bankrupt.

Outside of gambling, a lot of his financial issues game from legal battles with multiple parties, including several lawsuits with fellow rapper Rick Ross.

Not Paying Out...

Among the many bets 50 Cent has made, one in particular paints the famous rapper in a bad light and is relatively unknown.

During a boxing match between Terence Crawford and Yuriorkis Gamboa, there were rumors that 50 Cent bet rapper Webbie $1 million on the fight's outcome with Webbie betting on Crawford and 50 betting on Gamboa.

When Crawford won however, 50 Cent didn't pay up, and his team said they didn't know about any bet.

Rapping About His Gambling Habits

50 Cent not only lives out the gambling lifestyle, he brings it up in the lyrics of his songs as well. In the song What Do You Got, 50 raps "I got a gambling problem" which he has also admitted during interviews. 50 also raps "I lost money when I bet on Roy, won money when I bet on Floyd, I'm the one that bet on war", which, although never publicly stated, is most likely in reference to placing a wager on boxer Roy Jones Jr to beat Mayweather.

He also mentions in Body Bags that "I’m in the gambling spot", and in Rowdy Rowdy he raps "It's like a rollie with no ice, a gambling spot with no dice", showing that betting is always on his mind.

Where is 50 Cent Now?

50 Cent seems to have slowed down with sports betting and has instead gone down the route of financial betting, having a heavy presence in the stock market. He’s made quite the name for himself as a businessman and media persona. Just recently, he was part of a group that involved Shaquille O'Neal and Tyler Perry to purchase the Black Entertainment Network (BET).

50 is an executive producer on the popular Starz TV show Power and still acts. from time to time. with his next upcoming role being in Expend4bles. 50 also still performs as well, although not as frequent as he was at the peak of his rapping career.

In the fall of 2024, 50 also has plans for a book release. The topic will be around a suspenseful heist. In short, 50 Cent is a man of many talents. It would be no surprise to see 50 in the headlines again at some point in time to make another sports wager, whether it’s within the sport of boxing or perhaps back in the NFL playoffs.