Sean 'Diddy' Combs human trafficking investigation raid is 'just the beginning' of legal hurdles: expert

Sean "Diddy" Combs was once one of the most in-demand entertainers and producers in the industry, with a roster of major power players leading his Bad Boys Records label.

Through profitable music and business ventures, Diddy earned billionaire status in 2022, according to Forbes. 

His life in the spotlight hasn't always been so bright, though. On Monday, two of Combs' residences in Los Angeles and Miami were raided in connection to a federal human trafficking investigation. 

The music mogul declared his innocence in a statement provided to Fox News Digital, but legal experts warned that "the damage to his reputation may be irreparable" even if the investigation doesn't lead to his arrest or criminal charges.

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Monday's investigation also isn't Combs' first run-in with the law.

In April 1999, Combs was arrested and originally charged with felony second-degree assault and criminal mischief after attacking music executive Steve Stoute following a dispute over music video imagery involving his client, Nas. Combs later pleaded guilty to a lesser charge of harassment and reportedly paid Stoute $500,000 in an out-of-court settlement.

Nine months later, Combs, his then-girlfriend, Jennifer Lopez, and rapper Shyne, were at a nightclub in New York when gunfire broke out, injuring three people including a woman who was shot in the face. Lopez and Combs fled in his Lincoln and were later pulled over by NYPD for running a red light.

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A gun was found in the vehicle, and Jennifer and Sean were arrested. Lopez was let go, but Combs and Shyne were each charged with multiple offenses. While Combs was found not guilty at trial, Shyne was convicted on five of eight counts, and was sentenced to 10 years in prison. Lopez and Combs broke up in 2001 after dating for two years.

TV host Roger Mills sued Combs in 2001 and accused him of assault, false imprisonment and destruction of property, claiming Combs attacked him during an interview when he asked the rapper if he had any involvement in the death of Notorious B.I.G. Years later, a court sided in favor of "Diddy."

Gerard Rechnitzer claimed that Combs punched him and pushed his girlfriend outside of the Hollywood Roosevelt Hotel in a lawsuit filed in 2007. Combs settled the lawsuit one year later, and terms of the settlement were not disclosed.

In 2015, Combs was arrested and charged with assault with a deadly weapon stemming from an altercation with a coach at his son's college.

Sean allegedly swung a kettlebell at an assistant UCLA football coach after they yelled at his oldest son, Justin, now 30. "The various accounts of the event and charges that are being reported are wholly inaccurate," Nathalie Moar, a rep for Combs Enterprises, said in a statement to The Associated Press at the time. "What we can say now is that any actions taken by Mr. Combs were solely defensive in nature to protect himself and his son."

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Cindy Rueda, "Diddy"'s former personal chef, filed a sexual harassment lawsuit against Combs in 2017, and claimed she was "regularly summoned by Mr. Combs to prepare and serve entrees and appetizers to him and his guests while Mr. Combs and/or his guests were engaged in or immediately following sexual activity."

The suit was settled in 2019.

By 2023, Combs would be hit with multiple lawsuits. In November, Cassie, legally known as Casandra Ventura, accused "Diddy" of raping her in her own home, enduring "over a decade" of his "violent behavior and disturbed demands" and forcing her to have sex with male prostitutes while he watched and filmed. 

Combs denied Cassie's claims in a statement provided to Fox News Digital at the time.

"Mr. Combs vehemently denies these offensive and outrageous allegations. For the past six months, Mr. Combs has been subjected to Ms. Ventura’s persistent demand of $30 million, under the threat of writing a damaging book about their relationship, which was unequivocally rejected as blatant blackmail," his lawyer said. "Despite withdrawing her initial threat, Ms. Ventura has now resorted to filing a lawsuit riddled with baseless and outrageous lies, aiming to tarnish Mr. Combs’s reputation and seeking a payday."

One day after she filed the claim, Sean and Cassie came to an amicable resolution, and she dropped the lawsuit. "I have decided to resolve this matter amicably on terms that I have some level of control. I want to thank my family, fans and lawyers for their unwavering support," Cassie wrote. Combs said in his own statement that the decision was agreed upon by both parties, and he had no ill will towards the singer.

Three more women came forward with claims just before New York's Adult Survivors Act expired, each claiming sexual abuse by Combs in separate incidents.

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A music producer who sued "Diddy" for sexual assault in February added actor Cuba Gooding Jr. to his complaint Monday. Jones claimed he lived with the "I'll Be Missing You" singer for extended periods of time and accused Combs of unsolicited groping and sexual touching.

A U.S. official confirmed to Fox News that the raids on Diddy's homes Monday were connected to a federal human trafficking investigation. It's unclear if the rapper is the target of the federal agents' investigation.

Criminal defense lawyer Donna Rotunno said with HSI appearing at Diddy's doorstep, it's "just the beginning" as to what could come next for the three-time Grammy award-winning rapper who not only found his own success in the business, but also helped cultivate the careers of award-winning artists including Notorious B.I.G., Mary J. Blige, R&B singer Usher, Faith Evans, Mase, and Lil Kim.

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"They're looking for digital evidence, documents … financial records. Those are the types of things that they would be taking out of the house," Rotunno told Fox News Digital. "Logs of any type of records that would lend to the fact finding information that they're looking for. It's a serious thing. Trafficking could mean a whole lot of different things when it comes to … we don't know the ages of the people. We don't really know any of the allegations at this point."

Judie Saunders, a partner with ASK LLP, noted that Combs' "liberty, business, personal reputation and legacy are at all stake and may be subject to an immediate demise."

She told Fox News Digital, "The search of his residences by the Department of Homeland Security Investigations’ Transnational Organized Crime Division is a clear indication of the severity of the government’s investigation and possible charges that Combs may face in the near future."

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On Tuesday, Combs declared his innocence and denied the "meritless accusations" waged against him as he spoke out for the first time following the raids.

"Yesterday, there was a gross overuse of military-level force as search warrants were executed at Mr. Combs’ residences," his attorney, Aaron Dyer, said Tuesday in a statement provided to Fox News Digital. "There is no excuse for the excessive show of force and hostility exhibited by authorities or the way his children and employees were treated. Mr. Combs was never detained but spoke to and cooperated with authorities. 

"Despite media speculation, neither Mr. Combs nor any of his family members have been arrested nor has their ability to travel been restricted in any way. This unprecedented ambush — paired with an advanced, coordinated media presence — leads to a premature rush to judgment of Mr. Combs and is nothing more than a witch hunt based on meritless accusations made in civil lawsuits," he 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."