In Diddy and Britney Spears’ Legal Sagas, One Management Firm Appears

Tri Star Sports & Entertainment Group, the prominent celebrity management firm that was scrutinized for its involvement in Britney Spears’ conservatorship, is in the spotlight again for its work with Sean “Diddy” Combs as the hip-hop mogul, now in federal custody, fights sex-trafficking and racketeering charges.

Producer Rodney “Lil Rod” Jones’ February civil lawsuit against Combs contended that the music tycoon’s misconduct was made possible through a network of associates, including “Robin Greenhill, the accountant, [who] would ensure the wiring, funds transfer, or cash payments to sex workers.” Greenhill, a services director at Tri Star, didn’t respond to The Hollywood Reporter’s request for comment.

That civil claim presaged the Department of Justice’s allegations in its Sept. 17 indictment; Tri Star was not mentioned in that indictment.

In Spears’ best-selling 2023 memoir, The Woman in Me, she described Greenhill as Tri Star boss Lou Taylor’s “weird-ass lackey” and grouped both women alongside her despised father as “bullies.” The pop star wrote, “I wanted them out of my life.”

The New York Times in 2021 reported on Tri Star’s questionable involvement with Spears. The coverage enumerated how, according to a court investigator’s report, Greenhill had controlled Spears’ credit card and administered her medications. It also described how a security firm was allegedly hired by Tri Star, at Spears’ expense, to monitor the singer’s phone, record her in her bedroom and surveil the “Free Britney” activists who sought to expose the management company. “Screenshots of Ms. Spears’ text communications were shared with Ms. Greenhill,” the newspaper reported.

Tri Star is based in Nashville and Los Angeles. In 2019, Taylor told THR that her clients included Priyanka Chopra Jonas, Mary J. Blige, Reba McEntire, Aerosmith frontman Steven Tyler, Florida Georgia Line — and Combs, whom she recalled first meeting in the early 1990s, when she worked at a prior management firm and he was then an intern at Uptown Records. (Taylor’s other clients have included Gwen Stefani, Jennifer Lopez and members of the Kardashian family.)

Combs’ proposed bail package, which the magistrate judge rejected, would’ve been secured by the equity on his residence on the exclusive Star Island in Miami’s Biscayne Bay. His legal team told the court on Sept. 18 that the property was valued at $48 million, citing a 2022 appraisal undertaken by Tri Star.

Tri Star didn’t reply to questions from THR, including whether the company still represents Combs or whether it’s been approached by law enforcement officials involved in his criminal investigation and prosecution.