Fans are only now realizing that one of Diddy’s previous girlfriends was once romantically involved with his rival, Tupac Shakur.
In the 1990s, the hip hop scene was notorious for its rivalries, particularly the infamous East Coast-West Coast conflict. This battle, rooted in jealousy and gang issues, escalated into real-life violence, culminating in the tragic drive-by shootings of both Tupac and the Notorious B.I.G. within six months of each other.
For some background, before Diddy was known for his serious legal issues related to prostitution, he was the record producer for Biggie, having signed him to New York-based label Bad Boy Records. Meanwhile, Tupac was affiliated with Suge Knight’s Los Angeles-based label, Death Row Records.
What makes this story intriguing is that Puff Daddy, also known as Diddy or Sean Combs, not only dated but also fathered a child with the ex-girlfriend of his adversary.
In 1995, a year before Tupac’s untimely death at the age of 25, he was involved with Sarah Chapman from September to December. Fast forward ten years, and Chapman gave birth to her daughter, Chance Combs, with Diddy.
During that period, the now-disgraced music mogul was in a tumultuous relationship with his long-term partner, Kim Porter, from 1994 to 2007.
Porter was also expecting Diddy’s children at the time, twin daughters D’Lila Star Combs and Jessie James Combs, born in 2006. She eventually pointed to Diddy’s infidelity as a significant reason for their breakup.
As for Chapman, while she evidently had some kind of romantic involvement with Diddy, reports suggest they were merely friends by the time their daughter was born.
The tangled web of seven children with four different women was brought back into the public eye during Diddy’s high-profile sex trafficking trial over the summer. Many of his now-grown children were seen supporting him in court.
Quincy, Justin, Christian, Chance, D’Lila, Jessie, and Love Sean have largely remained supportive of Diddy since he was arrested by federal agents at a New York hotel in September 2024.
He faced charges including sex trafficking, racketeering, and transportation to engage in prostitution. However, he was ultimately sentenced to 50 months in prison for the latter charge, after being acquitted of the other, more severe charges.
Judge Arun Subramanian also ordered the father to pay a $500,000 fine.
Now, he is known to the prison staff as inmate #37452-054 at the Metropolitan Detention Center in Brooklyn, where he claims to be a ‘changed man’.
In a recent letter from his jail cell, he wrote to the judge: “The old me died in jail and a new version of me was reborn. Prison will change you or kill you – I choose to live.
“I no longer care about the money or the fame. There is nothing more important to me than my family.”
According to the Federal Bureau of Prisons’ online database, he will remain incarcerated until May 8, 2028.