(This article has been updated with the latest details.)

Sean Combs, more famously known as “Diddy,” has been a prominent figure in the realms of music, business, and politics since the late 90s, with connections to various Democratic and Republican leaders.

Recently, federal prosecutors claimed that Diddy exploited his celebrity status to force women into degrading sexual encounters for over 16 years, leading to three serious criminal charges including sex trafficking and racketeering. Diddy has denied all allegations.

His extensive relationships in the political sphere feature many notable figures at both national and local levels, including presidential hopefuls and mayors.

Diddy’s connection with former President Donald Trump dates back to 1998 when Trump attended Combs’ 29th birthday party. They both share a New York upbringing.

Trump featured in a video invite for the party, calling Combs “the legendary Puff Daddy,” as reported by Newsweek.

Throughout his career, Diddy has mainly championed Democratic initiatives, such as Rock the Vote and launching the Vote or Die campaign in 2004 to boost voter engagement.

Numerous Democrats have interacted with Combs, including Vice President Kamala Harris, former President Barack Obama, and Eric Adams, Mayor of New York City.

During her 2020 presidential campaign, Harris expressed gratitude to Combs on X (formerly Twitter) after he hosted a town hall focused on racial equality and COVID-19, which also featured Rev. Al Sharpton and Congresswoman Alexandria Ocasio-Cortez from New York.

While filming The Celebrity Apprentice in 2012, Trump referred to Diddy as a good friend, prompting contestant Aubrey O’Day to respond cautiously about his character.

Diddy, now 54, was arrested Monday following a grand jury indictment in New York City. The charges against him include sex trafficking through force or manipulation, racketeering, and facilitating prostitution, as outlined in an unsealed 14-page indictment.

A federal judge ordered that Diddy remain in custody, denying bail on Wednesday at the request of the prosecution. He is being held in the Metropolitan Detention Center in Brooklyn, which is known for its dilapidated conditions and violence amid severe staffing shortages, according to The New York Times. This facility has also housed inmates like R. Kelly and Ghislaine Maxwell.

Reflecting on his friendship with Trump in 2015, Combs noted that despite Trump being an unlikely candidate for the presidency back then, he appreciated his hard work.

However, by 2020, Combs had become critical of Trump, stating that “White men like Trump need to be banished” during an interview with Charlamagne tha God.

He expressed his desire for Biden to win the presidency, despite not being thrilled with Biden as a candidate, emphasizing the importance of holding him accountable once in office.

Diddy could face a life sentence or a minimum of 15 years in prison if found guilty of the charges against him.

Reporting by Reuters contributed to this article.

Melissa Cruz is a fellow covering electoral issues related to voter access for the YSL News Network. You can contact her at mcruz@gannett.com or on X, formerly Twitter, at @MelissaWrites22.