Fans are only just connecting the dots that one of Diddy's former girlfriends used to date his rival, Tupac Shakur.
The hip hop scene back in the 1990s was fuelled with rivalries, most famously the East Coast-West Coast feud that boiled over from jealousy and gang-related issues into real-life violence when both Tupac and the Notorious B.I.G were gunned down in drive-by shootings within six months of each other.
For context, before Diddy's name was associated with his hefty prison sentence for two counts of transportation to engage in prostitution, he was Biggie's record producer, signing him to New York-based label Bad Boy Records, while Tupac was signed by Suge Knight to the Los Angeles-based label Death Row Records.
That's why it's interesting Puff Daddy, also known as Diddy or Sean Combs, not only dated but went on to welcome a child with his arch nemesis' ex girlfriend.
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Back in 1995, a year before the 25-year-old rapper was killed, Tupac dated Sarah Chapman from September to December. Fast-forward a decade, and Chapman welcomed her daughter, Chance Combs, with Diddy.
At the time, the disgraced music mogul was still dating his long-term girlfriend, Kim Porter, in a rather rocky relationship spanning 1994 to 2007.
She, too, was pregnant with Combs' children at the time, twin daughters D'Lila Star Combs and Jessie James Combs, who were born in 2006. She went on to cite Diddy's infidelity as a major factor in their separation.
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As for Chapman, however, while it was clear she shared some sort of romance with Diddy, it is reported they were just friends when their daughter was born.
The messy web of seven children with four different women was put into the spotlight once again during Diddy's high-profile sex trafficking trial over the summer, during which many of his now-adult children were seen supporting their father in court.
Quincy, Justin, Christian, Chance, D'Lila, Jessie ,and Love Sean have largely stood by Diddy's side ever since federal agents arrested the 56-year-old from a New York hotel in September 2024.
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He was indicted on charges ranging from sex trafficking to racketeering and transportation to engage in prostitution, though was ultimately sentenced to 50 months in prison for the latter charge, after being acquitted of the other more serious charges.
Judge Arun Subramanian also ruled that the father pay a fine of $500,000.
Now, he's better known to prison staff as inmate #37452-054 in the Metropolitan Detention Center in Brooklyn from which he claims he is a 'changed man'.
Writing to the judge from his jail cell in a recent letter, he wrote: "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.
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"I no longer care about the money or the fame. There is nothing more important to me than my family."
He won't be released until May 8, 2028, according to the Federal Bureau of Prisons' online database.
Liv Bridge