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Sean ‘Diddy’ Combs: The ups and downs of a ‘bad boy’ turned businessman

Sean “Diddy” Combs once traced his success back to a pair of shoes.

One day, when he was a child, he asked his mother for a new pair of sneakers, but she couldn’t afford them. He recalled in a 2016 CNN interview that his mother almost began to cry upon hearing his request.

That day, he said, “my hustle was born.”

The man who famously once sang about being a “bad boy for life” had it pretty good for a long time, thanks to that hustle and his entrepreneurial successes.

Buying new shoes may not be a problem anymore but he has bigger ones — especially lately.

This week, authorities conducted searches on two of Combs’ homes as part of a federal investigation carried out by a Department of Homeland Security team that handles human trafficking crimes, according to a senior federal law enforcement official briefed on the investigation.

The probe reportedly stems from many of the same sexual assault allegations put forth in some civil lawsuits against him, according to a different law enforcement source familiar with the searches conducted on Combs’ homes.

Combs has been accused of sexual misconduct in five separate lawsuits filed in recent months – allegations he has repeatedly denied. It is unclear which allegations are included in the federal investigation.

Throughout his career, the tides have changed for Combs about as often as he’s changed his name. With his legacy in question, this particular chapter of the story of Sean “Diddy” Combs is currently punctuated more by an ellipsis than a period. But if he manages to rebuild a once towering professional empire in the aftermath of his present legal troubles, Combs’ image may one day be more synonymous with miracle worker than hitmaker.

Bad boy for life

Before the world knew him as Puff Daddy, P. Diddy, Puffy, Diddy and Love, Combs was building a career for himself and, most notably, as a producer for other artists, like Christopher Wallace, who was better known as Notorious B.I.G.

Combs signed Wallace to his label Bad Boy Records in 1993, going on to produce with the young talent hit records like “Big Poppa,” “Hypnotize” and “One More Chance” until 24-year-old Wallace’s murder in March 1997.

Christopher Wallace and Sean Combs around 1994. - Nitro/Getty Images
Christopher Wallace and Sean Combs around 1994. - Nitro/Getty Images

Months later, Combs, then only 27 himself, released his debut album, “No Way Out.” It included a tribute song to Wallace that remains one of Combs’ most memorable songs. “I’ll Be Missing You,” which sampled the The Police’s 1983 hit “Every Breath You Take,” was a massive hit for Combs and recording artist Faith Evans.

“I think I’ll always feel some sort of responsibility because I’m in this thing with him,” Combs told Wendy Williams of Wallace’s murder during an episode of her show in 2017. “He’s my artist.”

“Every Breath You Take” was the first rap song to debut as No. 1 on the Billboard Hot 100 and went on to win a Grammy.

His success continued with albums such as 1999’s “Forever” and “The Saga Continues…” which was released in 2001.

That same year, Combs was found not guilty of charges relating to a shooting incident outside a Manhattan night club in 1999, following a high-profile trial.

After the verdict, Combs told reporters that he would speak more on the matter at a later time, “but right now, I just want to go and be with my kids.”

He had two children at the time, but Combs is now a father of seven.

His first child, Justin, was born to Combs’ former girlfriend, stylist Misa Hylton, in 1993.

Combs’ long time, off and on relationship with model and actress Kim Porter resulted in the birth of son Christian in 1998. Twin daughters Jessie James and D’Lila Star followed in 2006.

Jessie James Combs, Chance Combs, Diddy, D'Lila Combs and Justin Dior Combs attend in September of 2023. - Jason Kempin/Getty Images
Jessie James Combs, Chance Combs, Diddy, D'Lila Combs and Justin Dior Combs attend in September of 2023. - Jason Kempin/Getty Images

Combs adopted Porter’s son, Quincy, from a previous relationship.

He also fathered daughters, Chance, with internet personality Sarah Chapman in 2006, and, Love, with cybersecurity professional Dana Tran in 2022.

In the world of business, Combs kept himself busy with ventures both during and after he peaked in the music world.

Branching out beyond music

Between his Sean Jean clothing line, his lucrative deal with Ciroc Vodka, his Revolt Media film and TV projects and his record label — among other ventures — Combs proved that “All About the Benjamins” wasn’t just a phrase in a song, it was a code he lived by.

Those once burgeoning brands and businesses, however, are not what they once were.

Founded in 1998, his Sean Jean clothing line once had annual retail sales of around $450 million by 2016, when Combs sold a majority stake to Global Brands Group, according to Women’s Wear Daily.

Combs won a bidding war to buy the brand back in 2021 after Global Brands Group went bankrupt.

“I launched Sean John in 1998 with the goal of building a premium brand that shattered tradition and introduced hip-hop to high fashion on a global scale,” Combs said at the time in a statement to Billboard. “Seeing how streetwear has evolved to rewrite the rules of fashion and impact culture across categories, I’m ready to reclaim ownership of the brand, build a team of visionary designers and global partners to write the next chapter of Sean John’s legacy.”

There was drama with some of his other business ventures.

In May 2023, he filed suit against Diageo PLC, his partner in the Ciroc vodka and DeLeón tequila businesses, alleging discrimination and that the company was limiting the reach of his brands by marketing them as “urban.”

Sean "Diddy" Combs poses with a bottle of Ciroc vodka in 2007. - Shannon Stapleton/Reuters
Sean "Diddy" Combs poses with a bottle of Ciroc vodka in 2007. - Shannon Stapleton/Reuters

That suit was resolved in January 2024.

“Sean Combs and Diageo have now agreed to resolve all disputes between them. Mr. Combs has withdrawn all of his allegations about Diageo and will voluntarily dismiss his lawsuits against Diageo with prejudice,” both parties said in a statement. “Diageo and Mr. Combs have no ongoing business relationship, either with respect to Cîroc vodka or DeLeón tequila, which Diageo now solely owns.”

His Bad Boy Entertainment label is still operating.

The hip-hop mogul was also known for the media company Revolt. In November of 2023, the company announced Combs had temporarily stepped down as chairman after being hit with a suit by former longterm girlfriend Cassie Ventura, in which she alleged that she had been raped and repeatedly abused by Combs during their more than decade long relationship.

Combs denied the allegations and the suit has been settled.

More legal troubles

The settlement was followed by four other civil suits filed in the past four months.

The cases returned to the spotlight this week when authorities swarmed homes owned by Combs in Los Angeles and Miami as part of a federal investigation carried out by a Department of Homeland Security team that handles human trafficking crimes, according to a senior federal law enforcement official briefed on the investigation.

Members of law enforcement are seen outside of Sean "Diddy" Combs' home in Los Angeles on Monday. - KCAL/KCBS
Members of law enforcement are seen outside of Sean "Diddy" Combs' home in Los Angeles on Monday. - KCAL/KCBS

“There was a gross overuse of military-level force as search warrants were executed at Mr. Combs’ residences,” Aaron Dyer, Combs’s attorney, said in a statement to CNN on Tuesday. “There is no excuse for the excessive show of force and hostility exhibited by authorities.”

Dyer added, “There has been no finding of criminal or civil liability with any of these allegations. Mr. Combs is innocent and will continue to fight every single day to clear his name.”

Several artists long associated with him have yet to comment about Combs’ legal issues publicly. CNN has reached out to some of his former collaborators, including Mary J. Blige, Faith Evans, MGK and Janelle Monáe, for comment.

Combs and his twin teenage daughters were preparing to leave Miami for a planned spring break trip on Monday when the searches happened, a source close to Diddy and with direct knowledge of the situation told CNN. He was briefly stopped by law enforcement and subsequently released

The source would not reveal Combs’ vacation destination or current whereabouts.

CNN’s John Miller, Elizabeth Wolfe, Eric Levenson, Denise Royal, Elizabeth Wagmeister and Carlos Suarez contributed to this report

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