On day four of the ongoing federal trial of Sean “Diddy” Combs, his former girlfriend, Casandra “Cassie” Ventura, spoke about her past relationship with industry insider Ryan Leslie.
Anthony Ryan Leslie is a singer, songwriter, rapper, record producer, and entrepreneur known by the nickname Castor Troy. During the cross-examination, Cassie admitted under oath that she began seeing Diddy while already in a relationship with Ryan in 2006.
The following year, she traveled to Miami with Combs under the false pretense of attending a professional event and ended up having a sexual encounter with him, thus cheating on Leslie.
Ventura also admitted that Ryan Leslie was nearly a decade older than her. When asked whether she had a tattoo of Castor Troy’s initials on her body, the Me & U singer confirmed it. She also shared that there were three tattoos in total, one of which was on her arm.
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All you need to know about Ryan Leslie and his relationship with Cassie
Ryan Leslie was born and raised in Richmond, Virginia. He is a music producer, artist, and businessman who has been active in the R&B and hip-hop industries since 1997.
He is credited with discovering R&B singer Cassie Ventura in 2004 and signing her to his record label, NextSelection. Two years later, Cassie also signed with Diddy’s Bad Boy Records collective as part of a joint venture with NextSelection.
Leslie, 46, wrote and produced Ventura’s 2006 debut single, Me & U, along with her self-titled debut studio album. Cassie also appeared on Ryan’s song Addiction, featuring Fabolous.
Ryan Leslie signed with Universal Motown Records to release his eponymous studio album in 2009, which included the songs "Addiction," "Diamond Girl," and How It Was Supposed to Be. He subsequently released two more albums titled Transition and Les Is More. His latest album from 2024 is called You Know My Speed.
Throughout his career, Ryan Leslie has collaborated with A-listers from the music industry, including Beyoncé, Kanye West, Britney Spears, Chris Brown, LL Cool J, Diddy, Cassie, and Usher, among others.
Ryan Leslie has previously been a member of the hip-hop group The Hitmen, which was signed to Diddy’s Bad Boy Records. He attended Harvard University, where he was also part of the institution’s oldest a cappella group, The Harvard Krokodiloes, or The Kroks.
The Grammy and BET Awards nominee also earned the AMBLE Vanguard Award in 2010 from his alma mater. In 2015, Leslie founded a direct text marketing service company called SuperPhone.
During a 2009 interview with DJ Vlad for VLAD TV, Leslie mentioned sharing a “very personal relationship” with Cassie during the start of her career, adding it was “close to everything that I loved.”
“I love Cassie. I love her... I fell in love with her. I fell in love with the music. I fell in love with her family and everything that it took for two young people in New York City hustling together. Um, it was inevitable,” Ryan shared back then.
When asked why the “rift” between him and Ventura happened, Leslie shared that there were many factors, situations, and nuances involved that he wasn’t comfortable discussing publicly. However, he did mention there were “specific” disputes, moments, and characters that played a role in the split.
Ryan Leslie declined to provide further details and said he didn’t want to get involved when asked about Ventura’s then-relationship with Combs and how it affected their professional collaboration. The video of DJ Vlad interviewing Leslie was posted on his YouTube page on May 15, 2024.
Cassie, during her Diddy trial testimony, didn’t disclose when she began dating Ryan Leslie. However, she confirmed that she cheated on him with Diddy in 2007 during a trip to Miami.
Ventura testified that she told Leslie it was a work-related event and even showed him a fake ad flyer for a nightclub appearance, thereby giving him the illusion of a business trip and avoiding his suspicion regarding her romantic and sexual involvement with Combs. Cassie also specified that originally, the nature of her relationship with the Love Album maker was strictly professional and platonic.
Diddy, 55, was arrested in September 2024 and charged with multiple criminal offenses, including racketeering conspiracy, sex trafficking by force, fraud, or coercion, as well as transportation to engage in prostitution. He has continued to deny all the charges.
Ventura, who dated him on and off between 2007 and 2018, testified for three consecutive days from March 13 to 15. She’s scheduled to reappear on Friday.
