50 Cent’s legal trouble continues to make headlines and the latest finds the rapper filing a lawsuit against his former defense team.

According to Business Insider, 50, who filed for Chapter 11 bankruptcy in July, accuses Garvey Schubert Barer of inept representation in the 2014 fallout with his former business venture, Sleek Audio headphones. The complaint was filed in a Connecticut court on Tuesday (October 6) with the G-Unit mogul seeking $75 million in damages.

In 2010, the rapper, born Curtis Jackson, teamed with Sleek Audio to create “Sleek by 50,” his own signature line of headphones. After a few false starts, including the missed launch date, the rapper went on to launch his own company, SMS Audio, with the assurance of his lawyers at GSB that he would not be violating any copyright property held by Sleek. However, the alleged assurance turned out to be wrong and Sleek eventually filed an arbitration against Jackson, who was forced to pay the massive judgment. The judgment also played a part in 50 filing for bankruptcy.

Over the summer, he lost a legal battle to the mother of one of Rick Ross’ children over a leaked sex tape. In a Manhattan court room, Jackson was ordered to pay $2 million in punitive damages to Lastonia Leviston, the woman featured in the sex tape, on top of a total of $5 million.