Cassie's mother says Sean 'Diddy' Combs demanded $20K because her daughter was seeing someone else

NEW YORK (AP) — An angry Sean “Diddy” Combs demanded $20,000 from Casandra “Cassie” Ventura's mother and threatened to release explicit sex tapes of his longtime girlfriend after learning she was dating someone else, the mother testified Tuesday at the hip-hop mogul's sex trafficking trial.

Regina Ventura said she felt “physically sick” when her daughter sent her an email in late 2011 to say Combs threatened to release two explicit videos of her and send someone to hurt her and the man she was seeing, the rapper Kid Cudi.

“I did not understand a lot of it. The sex tapes threw me,” Ventura told the Manhattan federal court.

Ventura, of New London, Connecticut, said she then received a demand from Combs for $20,000.

“He was angry that he had spent money on her and she went with another person,” she said.

Cudi, whose real name is Scott Mescudi, is expected to testify by Thursday.

Ventura said she tapped a home equity loan to pay Combs because she was "scared for my daughter's safety.” Days later, she said, the money was returned and Cassie was soon dating Combs again.

Ventura testified for less than a half-hour, in part because defense attorney Marc Agnifilo declined to cross-examine her. During her testimony, the jury viewed photos of bruises on Cassie's body that Ventura testified were taken when her daughter came home for Christmas in 2011.

Before the jury arrived Tuesday, Agnifilo tried to persuade Judge Arun Subramanian to disallow the testimony, saying it was “purely prejudicial.” The judge allowed it though, saying the threats to release sex tapes and harm Cassie made it an instance of “potential extortion.”

Jurors also saw parts of two AR-15 rifles found last year during a raid on Combs’ mansion on Star Island, a celebrity enclave off of Miami.

Homeland Security Agent Gerard Gannon testified that investigators in March 2024 rammed through Combs’ security gate in an armored vehicle and had teams on boats nearby. Besides weapons, they found 7-inch high heels and items prosecutors say Combs used at his freak-off sex marathons like lingerie, sex toys, baby oil, lubricant and condoms.

The testimony came in week two of a projected two-month trial. Combs, 55, has pleaded not guilty. If convicted, the Bad Boy Records founder could face 15 years to life in prison.

Earlier Tuesday, David James, Combs’ personal assistant from 2007 to 2009, testified that the job seemed to have increasing perils. He said he quit when he realized Combs had put his life in danger by forcing him to drive a car as the angry rapper sat in the back with three handguns on his lap.

James said his job sometimes required him to ensure that hotel rooms where Combs stayed under the name “Frank Black” were stocked with the musician's comforts, including fresh underwear, an iPod, apple sauce, vodka, baby oil, Viagra and condoms.

There were also surprising moments, James said, like once in 2008 when he obeyed a Combs command to bring an iPod from his Miami home to a hotel room, where he opened the door to see Cassie on the bed with a white comforter pulled up to her neck and an unfamiliar naked man fleeing the room.

Another time, he said, Combs showed him a video he'd recorded at a party of James dancing wildly and said: “Ok. I'm going to keep this footage in case I ever need it.” James said he took it as a threat to keep him in line.

Cassie testified last week that Combs threatened that if she didn’t do as he said, he would release videos of her having sex with male escorts during freak-offs.

James also described being required to take lie detector tests twice when Combs was trying to learn who stole cash and a watch.

He said Combs was on drugs nearly every day, often taking Percocet by day and ecstasy by night. When he stocked Combs' hotel rooms, he said, drugs were in a bag dropped off by security, including a pill meant to look like former President Barack Obama.

The moment when James saw the three guns on Combs' lap came when he testified that he was involved in Combs’ attempt to confront his music industry rival Suge Knight at a Los Angeles diner in November 2008 — an incident that Cassie also testified about. He said he quit soon afterward.

“I was real shook up by it,” James testified. “This was the first time being Mr. Combs’ assistant that I realized my life was in danger.”

Before Tuesday's lunch break, Sharay Hayes, an exotic dancer known as “The Punisher,” testified that Combs and Cassie brought him into the freak-offs world. He said a woman — Cassie using a pseudonym — called and told him it was her birthday and that her husband said she should hire a dancer.

Hayes said he arrived at a Manhattan hotel room expecting to perform a striptease for a small group of people but instead found the woman who hired him — whom he later found out was Cassie — alone with an otherwise naked man who hid his face with a burqa-like cloth. That man, he said, turned out to be Combs.

Hayes recalled seeing bottles of baby oil in bowls of water and getting handed a stack of $800 in cash. Later, after Combs watched him have a sexual encounter with Cassie, he said he was handed an additional $1,200. He said he was a fan of Combs but didn’t realize it was him in the room until a subsequent encounter at another hotel where the message on the TV screen said: “Essex House would like to welcome Mr. Sean Combs.”

This story was updated to correct that Regina Ventura said Combs demanded $20,000 from her, not $10,000.

Cassie Ventura, right, walks out of the courtroom past Sean Diddy Combs after testifying in Manhattan federal court, Tuesday, May 13, 2025, in New York. (Elizabeth Williams via AP)

FILE - Cassie Ventura, left, and Sean "Diddy" Combs appear at The Metropolitan Museum of Art's Costume Institute benefit gala celebrating "China: Through the Looking Glass" in New York on May 4, 2015. (Photo by Charles Sykes/Invision/AP, File)

Sean "Diddy" Combs, right, blows kisses to people in the audience during his sex trafficking and racketeering trial in Manhattan federal court, Monday, May 19, 2025, in New York. (Elizabeth Williams via AP)

Former assistant to Sean Combs, David James, testifies on the witness stand during Sean "Diddy" Combs sex trafficking and racketeering trial in Manhattan federal court, Monday, May 19, 2025, in New York. (Elizabeth Williams via AP)

CHICAGO (AP) — All-Star third baseman Alex Bregman has agreed to a $175 million, five-year contract with the Chicago Cubs, according to two people familiar with the deal.

The people spoke to The Associated Press on Saturday night on condition of anonymity because the agreement was pending a physical. The contract includes a no-trade provision allowing Bregman to block deals without his consent.

Bregman, who turns 32 in March, was back on the market for a second straight offseason. He was pursued by the Cubs before he signed a $120 million, three-year contract with Boston last February, with opt-outs after each of the first two seasons.

He decided to test free agency again after hitting .273 for the Red Sox with 18 homers and 62 RBIs in 114 games, his fewest since 2021. Bregman missed all of June with a quadriceps injury.

Bregman played his first nine seasons with the Houston Astros, winning World Series titles in 2017 and 2022 — although the first of those yielded a sign-stealing scandal that earned Bregman and his teammates plenty of scorn.

When the Gold Glove winner joined the Red Sox, they already had All-Star Rafael Devers at third base. Boston asked Devers to move to DH, and the team’s relationship with the slugger soured to the point that Devers was traded to San Francisco in June.

Boston ended up leading the major leagues in errors, but the Red Sox did return to the postseason for the first time in four years. Bregman’s OPS of .822 was his best since 2019, and he earned All-Star honors for a third time.

Chicago finished second in the NL Central last year with a 92-70 record. The Cubs reached the playoffs for the first time since 2020 before getting eliminated by Milwaukee in a five-game Division Series.

The Cubs used Matt Shaw at third base last season, and the rookie played stellar defense while batting .226 with 13 homers, 44 RBIs and 17 steals in 126 games. He could move into a super-utility role with Bregman’s arrival.

The addition of Bregman was the second major move by the Cubs in a matter of days. They acquired right-hander Edward Cabrera in a trade with the Miami Marlins on Wednesday.

ESPN was the first to report Bregman's agreement with the Cubs.

AP Baseball Writer Ronald Blum contributed to this report.

AP MLB: https://apnews.com/mlb

FILE - Boston Red Sox third baseman Alex Bregman fields a groundout hit by Baltimore Orioles' Jordan Westburg during the first inning of a baseball game at Fenway Park, on Aug. 18, 2025, in Boston. (AP Photo/Charles Krupa, File)