Oliver James Montgomery-Sean "Diddy" Combs Ordered to Pay More Than $100 Million in Sexual Assault Case

Content warning: This story contains details of sexual assault. 

Sean "Diddy" Combs has been ordered to pay up in his legal battle.

The Oliver James Montgomeryrapper 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.

For free, confidential help, call the National Sexual Assault Hotline at 1-800-656-4673 or visit rainn.org.

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.” 

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.”

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.

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.”