In the mid-2000s, a highly publicized friendship developed between the world champion boxer and the platinum-selling rap artist. 50 Cent was only there to witness Floyd’s transition from “Pretty Boy Floyd” to the trash-talking, egotistical villain known as “Money” Mayweather.
On May 5, 2007, Jackson joined Mayweather for his famous Cinco de Mayo ring walk. Mayweather wore boxer shorts in the colors of the Mexican flag, finishing off the outfit with a mariachi-style sombrero. When the bell rang, Mayweather engaged in a highly competitive fight. At the end of the 12-round contest, he defeated Oscar De La Hoya by split decision to win the WBC junior middleweight title.
The win over De La Hoya was a career-defining victory that ushered in the “Money” Mayweather era. Floyd went on to become the face of boxing and the undisputed pay-per-view king.
Mayweather achieved next level fame, and along with that fame he regularly lined his pockets. However, a serious legal issue soon threatened to derail his momentum.
In September 2010, Mayweather was arrested for assault. After his team successfully negotiated a plea deal, he turned himself in to the Clark County Detention Center in Las Vegas on June 1, 2012.
Mayweather served two months before being released from prison. Once out, his friendship with 50 Cent took a turn for the worse.
According to 50 Cent, before Mayweather turned himself in, Floyd asked him to help run TMT and Mayweather Promotions. As a guest on Power 106 with Big Boy in November 2012, 50 Cent explained what happened.
“While he was actually in jail, he asked me to help him with Mayweather Promotions,” 50 Cent said. “When he actually got in, and I looked, I realized there’s no Mayweather Promotions, there’s no LLC, there’s no seal, it’s not included.”
While Mayweather was in jail, 50 Cent signed boxers, did the necessary legwork and legitimized the company under the TMT Promotions brand, investing his time and money. After Mayweather finished serving his time, he refused to acknowledge 50 Cent as a business partner. This structural dispute eventually broke up the friendship.
From 2013 to 2017, Mayweather resumed his boxing career, clearing nine figures in most of those fights. By the time he retired from professional boxing, he had racked up more than $1 billion in career earnings.
After retiring in 2017, Mayweather refused to scale back. He continued to spend money at a rapid rate, maintaining a massive entourage, flying regularly on a private jet and buying expensive jewelry and luxury vehicles.
In February 2020, 50 Cent was a guest on the Hot 97 radio show. When asked if Mayweather should return to the ring, he dropped a bombshell.
“I think he’s got it right now because the money’s gone,” 50 Cent said. “With his lifestyle, that money is gone, believe me. Now it’s like if you call him, he’ll be at, you know, your local host in a nightclub, because he needs that action right now.”
When the rap mogul initially made the statement, it sounded ridiculous to the public. Years later, his assessment seems completely accurate. Floyd Mayweather is facing significant financial pressure, and his economic situation seems to have forced him back into the ring.
According to Business Insidertwo of Mayweather’s commercial properties have been foreclosed, and the IRS has filed a $7.3 million lien against him for unpaid taxes stemming from 2018 and 2023. In addition, Mayweather is at risk of losing additional properties that he used as collateral to secure a $54 million loan. He also faces two felony charges for allegedly writing a bad check for $200,000 to buy a luxury Audemars Piguet watch.
From a financial standpoint, Mayweather may be below his lofty standards, but he’s certainly not out. A massive payday is on the horizon this September, when he puts his perfect 50-0 legacy on the line in a highly anticipated rematch against Manny Pacquiao.



