Long before Cassie and Diddy were facing off in a courtroom, the singer was a rising star signed to Bad Boy Records. Fans have often questioned how her signing with Diddy’s label first came about, as well as why she released music so rarely following the success of her debut album. From her breakout moment to her recent claims that her career was being held back due to Diddy’s “freak-offs,” here’s what to know.
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Cassie’s Ex, Ryan Leslie, Helped Her Get The Deal
Cassie didn’t just stumble into the music industry; she had a man who claimed he would make her a star. Before Diddy even entered the picture, Cassie had signed to her then-boyfriend Ryan Leslie. He owned the record label NextSelection Lifestyle Group. While based in New York, the two had been cooking up music in the studio, including her debut single, ‘Me & U,’ which would go on to become her biggest hit to date.
Leslie was already a heavyweight, with a catalog of hits under his belt. And according to The New York Times, he brought in Tommy Mottola to manage Cassie under the executive’s management company. When ‘Me & U’ dropped, it shot up the charts, peaking at No. 3 on the Billboard Hot 100.
The general public was clearly feeling the song, and that’s when Leslie reportedly ran into Diddy at a club. He pitched him a partnership that would see Bad Boy Records team up with NextSelection to push Cassie’s already-finished debut album. Diddy agreed and signed her shortly after. Cassie’s self-titled album dropped in 2006, and she was officially on the map.
Cassie & Ryan Leslie Go Their Separate Ways
Within two years, Cassie wasn’t just Diddy’s artist; she was his leading lady. The tea on how things ended with Leslie remains unclear, but he’s always kept it classy. In a 2009 VLADTV sit-down, Leslie said, “I love Cassie. I fell in love with her, I fell in love with the music, I fell in love with her family.”
But when pressed about their fallout, he hinted at “specific characters” messing things up. Fast-forward to 2019, on The Breakfast Club, Leslie spilled that Cassie had started ghosting studio sessions for her second album with him, during which time she had already started dating Diddy.
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