Sean "Diddy" Combs Hit with New Civil Lawsuit Allegation of 2001 Rape by Woman Who Said His Penis was “The Length and Girth of a Large Tootsie Roll”

Sean "Diddy" Combs

Hip-hop mogul Sean “Diddy” Combs is facing fresh legal trouble as a new civil lawsuit has been filed against him by a woman identified as “Jane Doe,” who alleges that he violently raped her at his Park Avenue apartment in 2001. The lawsuit comes as Combs is already embroiled in multiple civil suits and a high-profile criminal trial in New York on sex trafficking charges, to which he has pleaded not guilty.

According to court documents filed in the Supreme Court of the State of New York, the plaintiff described meeting Combs in a Manhattan office building elevator. He invited her and her friends to a club, initiating a series of four social encounters over three months that the plaintiff’s lawyers describe as part of a calculated grooming process. The first two nights ended without incident, though on the second, the plaintiff says Combs attempted to kiss her in an SUV, which she rebuffed.

The third night involved a club outing that ended abruptly amid a commotion. When the plaintiff and her friend left without telling Combs, he allegedly called her, enraged, yelling, “Do you know who I am? No one does that to me!”

Sean "Diddy" Combs, 55, is on trial in New York federal court for sex trafficking, racketeering conspiracy, and transportation to engage in prostitution charges

The fourth and final night occurred on July 31, 2001. The plaintiff alleges she and a friend met Combs again at his Bad Boy Records studio before being transported—this time on a tour bus filled with “eight to ten large, imposing men”—to a Mos Def concert at the Bowery Ballroom. Onboard, they reportedly saw open condom wrappers, used condoms, and women's underwear. During the concert, both women began to feel unwell, and the complaint suggests their drinks may have been drugged.

After leaving the concert, they asked to be driven to the plaintiff’s Upper East Side apartment. Instead, Combs insisted on stopping at his own residence at 807 Park Avenue. Once inside, he allegedly led the plaintiff to his bedroom, locked the door, and again berated her for leaving the previous night. The complaint states that Combs then pushed her onto the bed, put a hand around her throat, held down her arm, and raped her.

Despite the trauma of the incident, the plaintiff recalled feeling “relieved” at the time due to the size of Combs' genitals, describing them as resembling a “large Tootsie Roll.” She later referred to him as “itty bitty Diddy” when recounting the incident in therapy and to friends.

Diddy, pictured here with ex-girlfriend Cassie Ventura, who testified against him on day three of his criminal trial for sex trafficking

After the assault, the plaintiff was escorted from the apartment by a bodyguard and reunited with her friend in an SUV that took her home. The complaint states she ignored all further communication from Combs and only came forward after undergoing therapy, which enabled her to speak about the trauma.

She now seeks unspecified compensatory and punitive damages for the physical abuse, sexual battery, emotional trauma, and psychological injury she alleges she suffered as a result of Combs’ actions.

The new lawsuit adds to Combs’ mounting legal troubles. He is currently incarcerated as his federal criminal trial on sex trafficking charges continues in New York. On the third day of proceedings, Combs’ former girlfriend, singer Cassie Ventura, testified that he had abused her for years, raped her after their breakup in 2018, and settled a $20 million civil lawsuit she filed in 2023.

Combs has denied all allegations and maintains his innocence.