50 Cent lost his battle with Sleek Audio, and has been ordered to pay $16 Million in damages, and attorney fees after trying to clear debt with the headphone company.

In 2013, Sleek Audio sued 50 Cent, after the headphone company invested over $1 Million to start a line of headphones with the rapper, when the 2010 deal fell through. 50 Cent started SMS Audio, and developed his Sync By 50 headphones, which were basically the same design as Sleek Audio‘s product, according to Sleek Audio.

Sleek Audio also sued 50 Cent for “misappropriating trade secrets, breaching his fiduciary duty owed to Sleek, participating in a civil conspiracy, breaching his confidentiality agreement with Sleek, and being unjustly enriched,” and had proof that 50 Cent‘s employees took over 4,000 potential customers information obtained via sign ups from a mini-site created by Sleek Audio.

According to information on HipHopDX, assistants of 50 Cent wrote back in forth via e-mail: “[Sleek] is onto us, LOL. They emailed and called … about the data.” and “Tell him something like, sorry, you just have to finish editing a video for 50 or something, we’ll get to it, LOL,” these e-mails were shown in the courtroom.

50 Cent was counter suing Sleek Audio, and claimed that they “fraudulently induced him into entering into an investment with them and breached their fiduciary duties to him,” but this didn’t hold up in the courtroom.

50 Cent is being ordered to pay $11,693,247 in damages and $4,488,331 in additional fees to Sleek Audio. 50 Cent‘s grand total to be paid to Sleek? $16,181,578.

Even for the rapper who penned hits like “I Get Money,” that has to be a major loss.