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Sean 'Diddy' Combs: the rap mogul facing life in prison

The Freeman

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May 03, 2025

Once hiphop's flashy impresario, Sean "Diddy" Combs now sports unruly, gray hair and only appears publicly in court, where he will be a regular starting Monday as his federal sex crimes trial gets underway in New York.

Jury selection will kick off the blockbuster proceedings, the next chapter for the once-powerful mogul, whose efforts in recent years to rebrand as "Brother Love" were thwarted by a criminal indictment and a mountain of civil suits alleging he committed harrowing sexual abuse.

The 55-year-old founded the Bad Boy record label in 1993, with proteges including the late Notorious B.I.G. and Mary J. Blige, and is frequently credited with moving hip-hop into the mainstream.

Combs, who has used various monikers over the years including Puff Daddy and P Diddy, amassed vast wealth, not least from his ventures in the liquor industry.

But despite his efforts to cultivate an image of a smooth party kingpin and businessman, the federal criminal case and multiple civil suits describe Combs as a violent predator who weaponized his fame to victimize men and women.

He has no major convictions but has long been trailed by allegations of physical assault, dating back to the 1990s.

One of the key elements in the New York trial will be his relationship with singer Cassie, whose real name is Casandra Ventura. The pair met when Ventura was 19 and he was 37, after which he signed her to his label and they began a romantic relationship.

In late 2023, she opened the floodgates against Combs with a litany of allegations against him, including a 2018 rape. Though that case was quickly settled out of court, a string of similarly lurid sexual assault claims followed-including one in December by a woman who alleged Combs and others gang-raped her when she was 17.

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