(This story has been updated to add new information.)
Rapper Sean Combs, commonly known as “Diddy,” is well known in music, business and political circles as both a Democratic and Republican candidate since the late 1990s.
But federal prosecutors say Diddy, one of hip-hop’s biggest names, used his fame to coerce women into degrading sexual acts over a 16-year period and was indicted on three criminal counts of sex trafficking and extortion on Monday. Diddy has pleaded not guilty to all charges.
Combs’ network of prominent politicians includes prominent figures in national and local politics, including presidential candidates, members of Congress and mayors.
The rapper’s relationship with former President Donald Trump, who, like Diddy, was born and raised in New York, first became public in 1998, when the real estate mogul was among the notables who attended the singer’s 29th birthday party.
Register to vote: Text the USA TODAY Elections team.
According to Newsweek, Trump also appeared in a video invitation to the party, calling Combs “the legendary Puff Daddy.”
Over the years, Combs has primarily supported Democratic causes, including founding Rock the Vote and the 2004 voter education campaign “Vote or Die.”
Democrats including Vice President Kamala Harris, former President Barack Obama and New York City Mayor Eric Adams have also had interactions with the music mogul.
Harris had posted a message of thanks to Combs on Twitter during her first White House campaign after he hosted a town hall on racism and COVID-19 in April 2020 that was also attended by the Rev. Al Sharpton and New York Rep. Alexandria Ocasio-Cortez.
MORE: Diddy gets photoshopped into Kamala Harris and Montel Williams photo | Fact Check
As for Trump, meanwhile, while filming “Celebrity Apprentice 5” in 2012, the reality TV host told contestant Aubrey O’Day, who worked for the hip-hop mogul, that Combs was a friend.
“I love Diddy. He’s a good friend of mine and a good guy,” Trump said, before asking O’Day, “Is he a good guy?”
“I don’t want to answer that question,” she said, looking away from the camera, before later revealing on a podcast that she was fired “not because of talent, but because I wasn’t willing to do what was expected of me in other ways.”
Combs, 54, was arrested Monday night after being indicted by a New York City grand jury. According to a 14-page indictment unsealed Tuesday morning, Combs is charged with sex trafficking by force, fraud or coercion, extortion and transportation for prostitution.
A federal judge denied Combs’ bail on Wednesday, granting prosecutors’ request to keep the rapper jailed until his trial at Brooklyn’s Metropolitan Detention Center, one of New York City’s most notorious jails.
According to The New York Times, MDC is New York City’s only federal prison and is known for its severely understaffed, aging infrastructure and uncontrolled violence. The notorious facility has previously housed notable inmates, including R. Kelly, Ghislaine Maxwell, and Sam Bankman Freed.
Combs was talking about his friendship with Trump in 2015, when the Republican was still seen as unlikely to run for president in 2016. “Donald Trump is my friend and he works very hard for him,” he told The Washington Post.
But by 2020, Combs had developed an aversion to Trump. “White men like Trump need to be kicked out. That kind of thinking is really dangerous,” he told Charmagne Tha God in an interview.
“When you think about it, we’re not without a choice. Say what you want about Biden, I can’t say I like his choices, but we have to get him into office and then we have to hold him accountable,” Combs concluded.
If convicted, the rapper faces a maximum sentence of life in prison and a minimum of 15 years.
Reuters contributed to this story.
Melissa Cruz is an election coverage fellow working on voter access issues for the USA TODAY Network. Contact her at mcruz@gannett.com or on X (formerly Twitter) @MelissaWrites22.
