Content warning: This story contains details of sexual assault.
Sean "Diddy" Combs has been ordered to pay up in his legal battle.
The rapper was ordered by a judge in Michigan's Lenawee County Circuit Sept. 9 to pay over $100 million to Michigan inmate Derrick Lee Cardello-Smith, according to court records viewed by E! News.
Judge Anna Marie Anzalone granted Cardello-Smith's motion for default judgment after Combs did not appear for the Sept. 9 virtual hearing, according to the local outlet Detroit Metro Times.
Cardello-Smith encountered the music mogul while working at a Detroit-area restaurant in 1997, according to his lawsuit against Combs obtained by Variety. The two men went to a party where they began having sex with two women when Combs allegedly touched Cardello-Smith. Cardello-Smith—who told Detroit Metro Times he is a self-taught student of civil and criminal statutes—then accused Combs of drugging his drink so he passed out, saying Combs later sexually assaulted him that evening, per the lawsuit.
Per public inmate records, Cardello-Smith is currently serving jail time on 12 sentences related to criminal sexual conduct and two sentences related to kidnapping.
Following the judgment, Combs' attorney Marc Agnifilo said in a statement to E! News that Cardello-Smith is solely looking to defraud the Bad Boys Record founder.
"This man is a convicted felon and sexual predator," the lawyer said, "who has been sentenced on 14 counts of sexual assault and kidnapping over the last 26 years."
He continued, "His resume now includes committing a fraud on the court from prison, as Mr. Combs has never heard of him let alone been served with any lawsuit. Mr. Combs looks forward to having this judgment swiftly dismissed."
E! News has reached out to lawyers for Cardello-Smith for comment, but has not heard back.
Cardello-Smith's lawsuit is the latest in a long line of legal troubles for Combs, who has been sued by six women—including ex-girlfriend Cassie—for sexual assault and abuse, allegations which the 54-year-old has denied. Cassie's lawsuit was settled in November 2023.
Recently, his ex Yung Miami—whom he dated off and on between 2021 and 2023—spoke out about her own time with the rapper.
"I can't speak on something that wasn't my experience," the City Girls rapper explained during an August episode of her REVOLT series Caresha Please. "I can't speak on something that I don't know. I can't speak on these allegations because I wasn't around at the time. I don't know that person, and that wasn't my experience."
She added that as "all these things came out I just needed to take a break and focus on what's important."
For a deeper dive into Combs' recent legal troubles, keep reading.
Search Warrants Executed on Sean "Diddy" Combs' L.A. and Miami Properties
Federal agents with Homeland Security Investigations (HSI) executed search warrants at Sean “Diddy” Combs’ Los Angeles and Miami properties on March 25, multiple law enforcement sources confirmed to NBC News.
The sources told the outlet the warrant was out of the Southern District of New York, and a spokesperson for HSI New York confirmed to E! News it “executed law enforcement actions as part of an ongoing investigation, with assistance from HSI Los Angeles, HSI Miami, and our local law enforcement partners.”
Law enforcement sources told NBC News the music mogul was in the Miami area when the search warrants were executed.
News about the investigation broke after Combs faced allegations of sexual misconduct in lawsuits filed by multiple accusers starting in November, with the musician denying the allegations.
“Sickening allegations have been made against me by individuals looking for a quick payday,” he wrote in a December statement posted on Instagram. “Let me be absolutely clear: I did not do any of the awful things being alleged. I will fight for my name, my family and for the truth.”
Diddy’s Attorney Speaks Out
The day after HSI executed the search warrants at Combs' L.A. and Miami properties, his lawyer spoke out.
"Yesterday, there was a gross overuse of military-level force as search warrants were executed at Mr. Combs' residences," attorney Aaron Dyer said in a March 26 statement to E! News. "There is no excuse for the excessive show of force and hostility exhibited by authorities or the way his children and employees were treated."
Dyer noted 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,” his lawyer's statement continued. “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.”
And Dyer expressed Combs' intent to defend himself.
“There has been no finding of criminal or civil liability with any of these allegations,” he added. “Mr. Combs is innocent and will continue to fight every single day to clear his name.”
Details About the Raid Revealed
As for what actually went down during the searches, multiple law enforcement sources familiar with the warrant told NBC News authorities with the Department of Homeland Security seized phones from Combs’ home in Miami before he was scheduled to travel to the Bahamas, and several sources familiar with the matter added that guns were discovered during the search.
One source familiar with the matter also told NBC News three women and one man were interviewed by prosecutors and investigators from the Southern District of New York about allegations of sex trafficking, sexual assault, the solicitation and distribution of illegal narcotics and firearms purportedly tied to Combs.
Diddy’s Associate Brendan Paul Arrested on Suspicion of Drug Possession
On the same day the search warrants were executed at Combs’ Miami and Los Angeles properties, one of his associates, Brendan Paul, was arrested by the Miami-Dade police on suspicion of drug possession, a law enforcement source familiar with the matter told NBC News.
According to the Miami-Dade arrest affidavit obtained by the outlet, Paul was taken into custody for allegedly possessing suspected cocaine and suspected marijuana candy.
Prison records obtained by NBC News show Paul was released on March 26 after posting bond.
“We do not plan on trying this case in the media,” Paul’s attorney Brian Bieber said in a statement obtained by the outlet, “all issues will be dealt with in court.”
In May, Paul accepted a plea deal, with his lawyer Bieber telling People, "Brendan accepted the prosecutor’s offer to permit his entry into the diversion program which, after completion, the case against him will be dismissed in its entirety."
Diddy Arrested in New York
He was arrested in the lobby of a New York hotel on Sept. 16, 2024, according to NBC News. It's unclear what Combs has been charged with and if the arrest has any potential connection to the raids.
“We are disappointed with the decision to pursue what we believe is an unjust prosecution of Mr. Combs by the U.S. Attorney’s Office," his lawyer Marc Agnifilo said in a statement to E! News. "He is an imperfect person but Is not criminal. To his credit Mr. Combs has been nothing but cooperative with this investigation and he voluntarily relocated to New York last week in anticipation of these charges."
Diddy Charged With Sex Trafficking & Racketeering
After Combs was arrested based on the sealed indictment, the indictment was unsealed on Sept. 17.
The 54-year-old was charged with racketeering conspiracy; sex trafficking by force, fraud or coercion; as well as transportation to engage in prostitution, according to court documents obtained by NBC News.
The indictment alleged Combs “abused, threatened, and coerced women and others around him to fulfill his sexual desires, protect his reputation, and conceal his conduct” for more than a decade, with prosecutors saying the purported behavior started around 2008.
"To do so," the documents stated, "Combs relied on the employees, resources, and influence of the multi-faceted business empire that he led and controlled—creating a criminal enterprise whose members and associates engaged in, and attempted to engage in, among other crimes, sex trafficking, forced labor, kidnapping, arson, bribery, and obstruction of justice."
According to NBC News, Combs pleaded not guilty and was denied bail.
“He’s going to fight this with all of his energy and all of his might,” his attorney Marc Agnifilo told reporters outside the courthouse prior to the arraignment, “and the full confidence of his lawyers."
Diddy Is Held Without Bail in New York Facility
Following his arrest, Combs was held at the Brooklyn Metropolitan Detention Center where he was denied a $50 million bond. The music mogul was also placed on suicide watch, which a source told E! News is a customary procedure for high-profile inmates. He was since taken off.
He was assigned the same area of the jail as cryptocurrency fraudster Sam Bankman-Fried, a source told NBC News.
Comedian Jeff Wittek Says He Attended "Freak Off"
Comedian Jeff Wittek, 34, came forward Sept. 29 to say he attended one of Diddy's "freak off" parties around 2010 in a Miami mansion.
"It was like eight stories high and it just kept going up," Wittek said on Jeff FM, "and the higher you went, the weirder s--t was going on."
"I saw live sex happen that night," he continued. "That's the first time I saw that happen ever in my life. And did I partake? No, but I got f--king drunk there."
As Wittek put it, "It's just crazy. I was literally there. I lived through it."
Diddy Accused of 120 New Sexual Assault Cases
In an Oct. 1 press conference, attorney Tony Buzbee detailed that 120 people had come forward with new sexual assault allegations against the rapper.
The allegations against Combs, Buzbee noted in a press conference with NBC News, include, "violent sexual assault or rape, facilitated sex with a controlled substance, dissemination of video recordings, sexual abuse of minors."
A lawyer for the rapper, Erica Wolff, later responded to the allegations, emphasizing that Combs maintains his innocence.
“He cannot address every meritless allegation in what has become a reckless media circus," she said. "That said, Mr. Combs emphatically and categorically denies as false and defamatory any claim that he sexually abused anyone, including minors."
Diddy Accused of Abusing Minors
One of the 120 accusers was only 9 years old when they were allegedly assaulted by Combs, their lawyer Tony Buzbee said in an Oct. 1 press conference, per NBC News.
According to the attorney, “25 of the accusers were minors at the time of the alleged incidents."
Diddy's Mom Janice Small Combs Defends the Rapper
“It is heartbreaking to see my son judged not for the truth, but for a narrative created out of lies,” Janice’s attorney Natlie G. Figgers shared in a statement on her behalf to The Hollywood Reporter Oct. 6. “To bear witness what seems to be like a public lynching of my son before he has had the opportunity to prove his innocence is a pain too unbearable to put into words. Like every human being, my son deserves to have his day in court, to finally share his side, and to prove his innocence.”
Beyoncé and Jay-Z's Lawyer Calls Out Piers Morgan Over Diddy Comparisons
Beyoncé and Jay-Z's lawyer spoke out after Piers Morgan's TV guest Jaguar Wright claimed the couple had more “victims” than Diddy.
"There’s rumors, and then there’s nonsense, and this is one step further,” lawyer Alex Spiro told TMZ Oct. 9. “This is a formal and pointed accusation of something.”
Their attorney told Piers to “remove that false accusation," which the host later did and apologized.
“As I noted in the moment," Piers said on his Oct. 8 show, "they were not present to respond or defend themselves. But now they have: their lawyer has contacted us to say those claims are totally false and have no basis in fact.”
Odell Beckham Jr. & Druski Accused
In an amended complaint originally filed in Oct. 2024, defendant Ashley Parkham accused Odell Beckham Jr. and Druski in March 2025 of participating in a gang rape of her with Combs in 2018.
Diddy pleas not guilty again
In March 2025, Combs appeared in court again to plead not guilty to allegations made in a superceding indictment that accused him of forcing employees to work long hours and threatening them with retaliation.
A judge dismisses one sexual assault case filed against Diddy
After a judge ordered that a Jane Doe plaintiff had to identity herself and refile a lawsuit—first filed in October 2024—accusing Combs of sexual assault, the case was dismissed when the plaintiff did not refile within the allocated time frame.
Jury Selection Begins
On May 5, 2025, one week before the trial’s opening statements take place, jury selection began—with the jury being comprised of 12 people and 6 alternates.