DIDDY's former assistant recounts how Mr. COMBS once told him, he had CASSIE “right where he wanted her”

Wednesday, May 21, 2025 - One of Sean "Diddy" Combs' former assistants testified Monday in the music mogul’s ongoing federal trial, recounting conversations he says he had with singer Cassie during the early stages of her relationship with Diddy. 

The assistant, David James, took the stand as a prosecution witness and offered insight into what he described as Cassie's sense of entrapment in the relationship.

James told the jury he worked for Diddy between 2007 and 2009, and first met Cassie on Star Island in Miami, where Diddy had rented a yacht to impress her. During a quiet moment on the dock, James said he and Cassie were smoking cigarettes when she remarked, “Man, this lifestyle is crazy.” When he advised her to leave if she felt that way, she reportedly responded, “I can’t. I can’t get out.”

According to James, Cassie confided that Diddy was financially and professionally responsible for nearly every aspect of her life, from her music and career development to her apartment and living allowance. “I didn’t think she could easily leave,” James told the court, echoing previous testimony from Cassie’s former friend, Kerry Morgan, who also stated that Cassie felt trapped due to Diddy's control over her job, car, and housing.

James further recalled a second conversation that took place in a taxi at the Sundance Film Festival. He testified that Cassie had been excited about a new album and shared a track list with him, though he noted that, to his knowledge, the album was never released.

In addition to his interactions with Cassie, James testified about Diddy’s romantic behavior, saying the music executive dated multiple women simultaneously but often referred to Kim Porter as his “queen.” He also claimed that Diddy once told him he had Cassie “right where he wanted her,” describing her as “moldable.”

James recounted his interview process for becoming Diddy’s assistant, telling jurors about a meeting with a human resources executive at Bad Boy Entertainment who allegedly told him, “This is Mr. Combs’ kingdom and we are all here to serve him.”

Court proceedings were adjourned for the day while James was still on the witness stand, and his testimony is expected to continue Tuesday, May 20.