A judge has reportedly ordered 50 Cent to pay Sleek, a headphone company the New York rapper once worked with, more than $16 million, according to Radar Online

50 Cent’s legal issues with Sleek have been ongoing. In 2013, Sleek sued 50 Cent. The G-Unit head was set to work with Sleek and invested $1 million to start his line of headphones through the company. However, 50 Cent eventually developed Sync by 50 with another company. Sync by 50, Sleek says, featured “basically the same design, mechanically” as the line it had previously developed for 50 Cent. 

Moreover, Sleek 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,” according to Radar Online. Sleek claimed 50 Cent and his assistants pulled private confidential information off a website Sleek created. The website had close to 4,000 potential customers’ e-mail addresses, among other data. When the data disappeared from Slee’s servers following 50 Cent’s team receiving the site’s password, his assistant reportedly wrote, “[Sleek] is onto us, LOL. They emailed and called … about the data.” Another assistant also commented on this. “Tell him something like, sorry, you just have to finish editing a video for 50 or something, we’ll get to it, LOL,” the assistant reportedly said. 50 Cent has counter sued, saying Sleek “fraudulently induced him into entering into an investment with them and breaching their fiduciary duties to him,” according to the publication. In May 2013, an arbitrator denied 50 Cent’s claims and granted Sleek’s. 

As a result, 50 Cent was ordered to pay $11,693,247 in damages and additional fees.

Since the May ruling, 50 Cent has reportedly fought the fees, however an arbitrator signed a final agreement this week. 

In a final statement, the arbitrator wrote that Sleek’s founders “did not have a good head for business…Thus the arbitrator can sympathize with [Curtis “50 Cent”] Jackson’s growing frustration that he was putting money into Sleek and not, in his opinion, seeing the results that he assumed would be forthcoming on a timely basis. Likewise, the arbitrator can appreciate the [Sleek team’s] frustration with what they perceived to be Jackson’s team taking control of their company … However, Jackson’s frustrations do not justify the actions he took or were taken on his behalf …”

In this week’s ruling, the fees were announced as $4,488,331, making the total amount $16,181,578.

In 2011, HipHopDX reported on 50 Cent’s split from Sleek. “The license arrangement between my company, G-Unit, and Sleek Audio to produce headphones branded as ‘Sleek by 50’ has been cancelled,” 50 Cent said at the time. “Instead, I have established a new company that is developing a complete line of audio accessories, including wireless headphones, offering superior sound quality along with cutting edge technology for all music lovers to enjoy…As an artist, I am committed to bringing top-of-the-line audio products to my fans, and I am excited that I have the resources to achieve just that with this new venture.”

(April 8, 2014)

UPDATE: According to the Palm Beach Post, 50 Cent has lost a fight to erase the $16 million debt. 

Palm Beach County’s Judge Peter Blanc reportedly said that there wasn’t a good reason to clear the debt provided by 50 Cent and his legal team. As a result, 50 has been ordered to pay Sleek the $16 million. 

RELATED: 50 Cent Explains Split with Sleek Audio