50 Cent recently got back on board with Floyd Mayweather.

But he might be losing his other big connection to boxing.

TMZ reports that Fif's boxing company SMS Promotions  filed for bankruptcy yesterday. 50 founded SMS in 2012 and signed big name fighters like Yuriorkis Gamboa, James Kirkland and Andre Dirrell. SMS hosted an event on May 15, but it wasn't enough to get them in the black. According to Chapter 11 filings, SMS has between 100K and 500K in debt.

In court papers, SMS vows to emerge from bankruptcy stronger. "Under the direction of Mr. Jackson [50 Cent], SMS Promotions looks forward to reorganizing as a new corporate entity and becoming one of the leading promotion companies in the world of professional boxing," wrote the company's lawyer.

50 Cent isn't the only rap legend who's struggled to get his foothold in the business of the sweet science. Jay Z's Roc Nation foray into boxing management has also been rocky.