Diddy’s ex-assistant tells jury he set up hotel rooms for ‘Freak Offs’

Editor’s Note: This story contains discussions of rape or sexual assault that may be disturbing. Reader discretion is advised. If you or someone you know has been sexually assaulted, you can find help and discreet resources on the National Sexual Assault Hotline website or by calling 1-800-656-4673.

(NewsNation) —The federal trial against Sean “Diddy” Combs resumes Tuesday with his former personal assistant, David Jones, returning to the stand. 

Prosecutors continued their questioning of Jones, who worked for Combs from 2007 to 2009. 

Jones gave emotional testimony Monday, saying one of Combs’ staff members pointed to a photo of Combs on the wall and told him, “This is Mr. Combs’ kingdom. We’re all here to serve him.”

Ex-Diddy assistant testifies rapper said Cassie was ‘moldable’ and ‘young’

Combs had described Casandra “Cassie” Ventura as “moldable” and also said “she’s good. I got her right where I want her. She’s young,” to James, he testified.

He also said he told Ventura to leave Combs after seeing his treatment of her, and she told him, “I can’t. I can’t get out. You know, Mr. Combs oversees so much of my life.”

James testified that he never witnessed Combs physically assaulting Ventura, however he did observe the two have numerous arguments over the direction of the singer’s career.

Part of his role as Combs’ assistant was to set up hotel rooms ahead of time for his boss, which was referred to as “advancing” rooms.

Ex-Diddy assistant set up hotel rooms with baby oil, Viagra, and drugs

James brought Combs’ Louis Vuitton bag which contained roughly $10K in cash and a medicine bag that held 25-30 pill bottles carrying Viagra, Tylenol, and Percocet. Combs also took Ecstasy pills with President Obama’s face on them.

The former Combs assistant also purchased lubricant for the fallen music mogul, but with cash as he was told the musician did not want those items tracked back to his record company.

James recalled an incident in Miami in 2008, when he entered a hotel room when Ventura was asleep with an unidentified naked man wearing a condom and Combs was in the shower. The man left when James came into the room.

  • Courtroom sketch of Sean "Diddy" Combs
  • A courtroom sketch of Sean "Diddy" Combs
  • A courtroom rendering of Sean "Diddy" Combs, right, looking at jurors as they file into the jury box

Diddy would conduct business under the influence of drugs, ex-assistant says

The former assistant testified that Combs would do drugs daily and conduct business under the influence. When asked if Combs did drugs in the studio, James replied, “Of course.”

James said he bought drugs for Combs or his friends twice, and he himself only took drugs once one New Year’s Eve.

He said that Combs called him in and asked if he was dancing around. According to James, Combs had a videographer present at his parties.

Combs allegedly told James, “Ok. I’m going to keep this footage in case I ever need it.”

The ex-assistant said the release of that footage would be embarrassing for him.

James testified that Combs made him take lie detector tests on two occasions when the record label executive was trying to find out who stole money and a watch.

Ex-Diddy assistant recalls armed Suge Knight encounter

In November 2008, James said on the stand that he was involved in the incident Ventura recalled during her testimony that Combs took guns to confront Suge Knight.

James testified that he was in the vehicle with a Combs’ bodyguard at 4 AM to pick up food from Mel’s Drive-In when the security guard allegedly spotted someone handing a gun to Knight.

James said he and the bodyguard returned to Combs’ house roughly 10 minutes away from the restaurant.

Combs wanted to go to the diner, and Ventura was yelling at him not to go, James testified.

James said Combs told him to drive him and the security guard, D-Roc, to the diner. While driving James said he saw the rapper have three guns on his lap in the car.

When they got to the diner, Knight and his group, had already left, James recalled.

Combs, the security guard, and James returned to the Los Angeles residence.

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

Cassie’s mother testifies Diddy demanded $20K to stop release of sex tapes

Ventura’s mother, Regina Ventura, testified on Tuesday that the rapper threatened to release sex tapes of her daughter after learning the singer was dating Kid Cudi.

In 2011, Ventura received an email from her daughter claiming that Combs was going to publish sexual material of her, and threatened to hurt the singer, and Kid Cudi. She felt “physically sick” after learning this information.

In her less than thirty minutes on the stand, Ventura said, “I did not understand a lot of it. The sex tapes threw me.”

Ventura testified that Combs demanded $20,000 in order “to recoup money he had spent on her because he was unhappy she was in a relationship with Kid Cudi.” She added that the music label executive “was angry that he had spent money on her and she went with another person.”

In order to come up with the hefty sum, Ventura took out a home equity loan because she was, “scared for my daughter’s safety.”

The money was returned shortly after, and Combs and Cassie reconciled.

Photos were shown of her daughter’s thigh, lower back, and shoulder bruised. Ventura said, “She was beaten by Sean Combs.” She testified that images were taken in December 2011, and it was when her daughter told her she was abused by the hip-hop mogul.

Male exotic dancer testifies he was hired to create a “sexy scene” with baby oil

Sharay Hayes, who worked as a male exotic dancer under the name “The Punisher,” said on the stand on Tuesday that he was hired in Fall 2012 by Ventura and Combs.

He said a woman called him under the guise of a birthday party, but when Hayes arrived there was no party.

Hayes said that he did not recognize Ventura at first. She was wearing a wig and a bathrobe. She informed him that he was there to create a “sexy scene” with baby oil.

The stripped was told the woman’s husband would be entering the room and to not acknowledge him.

A naked Combs entered with a face covering and holding lubricant. The former music label executive did not engage with Hayes. Combs sat behind a table and masturbated and gave Ventura “subtle directions.”

After about 25-45 minutes, Combs exited, and Ventura followed him.

Ventura returned and asked if he wanted to “finish.” Hayes rejected the offer.

Cassie’s former friend testifies about alleged abuse

James follows the testimony of Ventura’s former friend Kerry Morgan, who corroborated that Combs engaged in violence with the singer. 

Morgan said she saw the rapper assault Ventura twice, pulling her hair, kicking her and pushing her.

Witness Kerry Morgan arrives at Federal Court for the Sean “Diddy” Combs trial, on Monday, May 19, 2025, in New York. (AP Photo/Ted Shaffrey)

She also said Ventura was at the fate of Combs and that once she heard the record label executive say he “owned” his then-girlfriend and signed artist.

Morgan said she was also at the receiving end of his violence in 2018 when Combs choked and then smashed a wooden hanger on her head when she came to Ventura’s Los Angeles home enraged because he thought Ventura was dating someone else.

The attack left her with a concussion, Morgan told jurors. 

Morgan told jurors she was going to sue Combs but that Ventura made her sign a nondisclosure agreement in return for $30,000 to keep quiet while also accusing her of “milking” and “overexaggerating” the attack. 

The episode ended their long-term friendship, and the two haven’t spoken since, she said. 

Combs is facing federal charges of racketeering conspiracy, sex trafficking by force, fraud or coercion and transportation to engage in prostitution.

The Associated Press contributed to this report. 

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What to expect when you’re expecting a budget

Gov. Kathy Hochul announced that lawmakers had overall reached an agreement over the state budget last week but details are still being fleshed out.

DAYS THE BUDGET IS LATE: 41 

SPENDING SPECIFICS: Crucial state budget details — including aid for New York City, the structure of a surcharge on high-value second homes and the contours of major pension changes — are yet to be fully ironed out.

Gov. Kathy Hochul last week announced a "general agreement" for a $268 billion spending plan — but without specifics on many items. The closed-door discussions remain underway in Albany and none of the nine remaining budget bills have been printed.

The state budget is now destined to be at least six weeks past its March 31 due date. Yet Hochul is counting on voters to appreciate her policy wins and not focus on what has been an at-times messy process.

Hammering out these final specifics won't make or break a final deal. But the fine print will matter for how much New York plans for its massive tax-and-spend plan — impacting some 19 million people.

Here's what's to still expect when you're expecting a budget.

New York City aid: More help for the Big Apple is on the way from Albany. Lawmakers and Hochul are discussing additional foundation aid, potentially changing the formula for how public education spending is determined, and more cash for homeless students. At the same time, enabling legislation for pension amortization is being considered.

Those measures are designed to help New York City Mayor Zohran Mamdani close what's left of a $5.4 billion budget gap. And they come on top of the additional $1.5 billion Hochul agreed to earlier this year.

The governor told reporters Monday morning her office has been working well with the Mamdani administration to fix the city's budget woes.

"There's quite a bit that needs to be OK'd by New York state," she said. "I spent last night talking to the mayor, Friday night talking to the mayor. It's been a great level of cooperation."

Pied-à-terre structure: Lawmakers are yet to see any detailed budget language for Hochul's proposed surcharge on non-primary second residences worth $5 million and above. How that surcharge is structured — including how much it will rely on a home's assessed value — will matter for how many residences are actually captured by the tax.

Overhauling Tier 6: Overhauling the Tier 6 pension category is a potentially costly endeavor. Hochul and lawmakers are now considering what's being called a "skinny" version of a plan originally pushed by unions, according to two people familiar with the talks.

The change would lower the retirement age for teachers to 58 after 30 years of service, but it would not alter how much they contribute from their paychecks. For the rest of the public workforce, contributions of no lower than 3 percent of a worker's take-home pay is under consideration, but no change would be made to their retirement age.

The move is expected to cost $500 million combined for the state, local governments and school districts. That's far less than the $1.5 billion proposal advanced earlier this year by the New York State AFL-CIO.

Buffer zones: As POLITICO Pro reported earlier, lawmakers and Hochul have weighed a 50-foot protest buffer zone that would allow local officials to expand it as they see fit. Having those zones around houses of worship is largely agreed to, but working through the specifics remains a sticking point. Nick Reisman

From the Capitol

Three New Yorkers linked to a cruise ship with a hantavirus outbreak are being quarantined in Nebraska.

HANTAVIRUS IN NEW YORK: Three New Yorkers were aboard a cruise ship at the center of an international hantavirus outbreak, state Health Commissioner James McDonald said in a statement this afternoon. The three passengers were sent to the Offutt Air Force Base in Nebraska, where they are expected to be subject to a 42-day monitoring period, according to McDonald.

"While the Department is working in close coordination with the Centers for Disease Control and Prevention and local health departments to gather information, at this point it is unclear how long they will stay in Nebraska and whether, or when those individuals intend to return to New York,” McDonald said.

“At this point, it is important to emphasize that there is no immediate risk to the public. We will continue to monitor the situation and provide updates as needed," he added.

When asked about the threat of the virus to New Yorkers, Hochul said the state health agency is working with the CDC, and she is monitoring the federal government to make sure officials have the capacity to handle any potential outbreak.

“I want to make sure that the CDC is capable of handling something that could be larger than they are predicting, and I say that because I know that over a year ago, there were significant cuts to the CDC,” Hochul said. “We have outstanding resources here in the state of New York…so I’ve activated them to start preparing New York for worst-case scenarios and hope they do not come.”

She noted that the state is putting together a plan to address any spread of the virus, but she does not believe it will turn into another coronavirus pandemic. She said she will begin doing briefings if it spreads beyond the three individuals flown in from the ship. — Katelyn Cordero 

GOV’S SOCIAL ACCOUNT GETS PLAUDITS: The state government’s eyebrow-raising, joke-telling, irreverent social media accounts were honored with a Webby Awards “Honoree” award last week, Hochul’s office told Playbook.

The accounts, which go under the handle @NYGov on Instagram and X, are separate from the “Governor Hochul Press Office” account, which drew the ire of Barstool Sports founder Dave Portnoy last week when it mocked him for his age.

@NYGov, also known as “State of New York” on X, most recently posted messages like “it’s hole filling season” to spread the word about the state’s pothole reporting hotline on X, or "UNALIVE THOSE FLYS" as an Instagram PSA on the invasive spotted lantern fly.

“I’ve always believed that government is for the people, and in order to reach people, we need to communicate like them,” said Milly Czerwinski, a digital content strategist who works in Hochul’s comms shop and runs the account. “NYGov’s oddity and authenticity has broken down the traditional bureaucratic barriers to reach millions of people. Being weird works — this award is proof of that.” Jason Beeferman

FROM CITY HALL

The Civilian Complaint Review Board, which investigates and prosecutes cases of police misconduct, has received Chi Ossé’s claim and is reviewing it, a spokesperson confirmed.

CCR-CHI COMPLAINT: City Councilmember Chi Ossé filed a misconduct complaint today against an NYPD officer who arrested him, advancing a case that stands to drive a further wedge between the police department and Mayor Mamdani.

The complaint, which Ossé shared with POLITICO, alleges the officer used excessive force during the April 22 arrest in Brooklyn, where the Council member and others were protesting the planned eviction of a woman who claims she’s the victim of deed theft.

The Civilian Complaint Review Board, which investigates and prosecutes cases of police misconduct, has received Ossé’s claim and is reviewing it, a spokesperson confirmed.

Ossé, a democratic socialist and ally of Mamdani, told POLITICO he believes the arresting officer violated his civil rights. “My rights were violated, but more importantly, my responsibility to my community and constituents demands a fact-finding,” said Ossé, who claims he suffered a concussion from being slammed to the ground.

The NYPD previously said Ossé and three other protesters were only arrested after refusing verbal commands to stop blocking access to the property where the eviction was set to be executed.

A spokesperson for Mamdani — who called video of Ossé’s arrest "incredibly concerning” last month — said in response to the Council member’s complaint that "the mayor respects the independence of the CCRB and will allow the disciplinary process to play out based on the evidence, established procedures, and the NYPD’s disciplinary matrix."

Mamdani, a longtime NYPD critic, faces a fraught situation in responding to Ossé’s complaint.

If he doesn’t back up his fellow democratic socialist, Mamdani is likely to anger his allies on the left. On the flipside, if he condemns the arresting officer, he risks drawing the ire of NYPD leaders, including Commissioner Jessica Tisch, as well as the department’s rank-and-file cops.

Read more about the CCRB and Ossé from Chris Sommerfeldt in POLITICO.

CASE CLOSED: Council member Vickie Paladino has reached a settlement with the City Council to resolve disciplinary charges focused on her controversial social media posts.

The takeaway? The Council has withdrawn its disciplinary charges, and Paladino is dropping her lawsuit challenging the proceedings.

The agreement, filed in Manhattan Supreme Court on Monday, effectively dismisses the charges and cancels an ethics hearing that could have led to censure, fines or expulsion. As part of the settlement, Paladino must delete three posts cited in the case. She must also remove “Council Woman” from her personal X account display name within 48 hours of court approval to communicate to the public a clearer separation between her official posts, which are subject to some of the Council’s rules and regulations, and her personal opinions, one member familiar with the parameters of the settlement told Playbook.

The case stemmed from a string of inflammatory posts starting in December where, in a deleted post, she called for the “expulsion of Muslims from western nations,” prompting the committee to look into her conduct.

In February, she posted that New York was under “foreign occupation” following Mamdani’s appointment of a top immigration official. Paladino questioned whether the administration included “one single actual American” and later described a photo of Muslim sanitation workers praying as part of an “Islamic conquest.”

The Council’s Rules and Ethics Committee had charged Paladino with disorderly conduct and violations of its anti-harassment and discrimination policy in March.

Paladino sued to block the proceedings, arguing she was being targeted for her conservative views and that the discipline violated her First Amendment rights.

As part of the settlement, Paladino must issue a statement saying she did not intend to make colleagues or staff feel “unwelcomed or unsafe.” Council member Sandra Ung, who chairs the ethics committee, issued her own statement Monday afternoon saying the resolution “strikes the balance” between protecting staff and lawmakers’ free speech rights.

Both sides agreed to issue limited public statements and refrain from further comment. — Gelila Negesse

FROM THE CAMPAIGN TRAIL

Rep.Pat Ryan is the latest member of the New York delegation to weigh in the NY-12 primary election.

EYES ON AI: Rep. Pat Ryan is backing state Assemblymember Alex Bores to succeed retiring Rep. Jerry Nadler, making him the latest member of the New York delegation to weigh in on one of the state’s most competitive primary elections.

In making his endorsement, the Hudson Valley Democrat cited the high-profile AI fight that’s become a central theme of the race as a key reason for backing Bores.

“He’s going to be the next member of Congress for the New York 12th District,” Ryan said at an event in Midtown with Bores today. “If you have any doubt, you don’t have to take my word for it — follow the money. Look at the incredible unprecedented amount … It’s because these tech billionaires are terrified, they’re terrified of Alex specifically.”

The millions of dollars in spending by a pro-artificial intelligence super PAC against Bores — an alum-turned-critic of data analytics company Palantir and a sponsor of the AI safety RAISE Act in the state Legislature — has also drawn an influx of money from regulation-friendly AI and tech-affiliated groups to boost him.

Bores’ campaign said that both he and Ryan “share a belief that the next Congress must take decisive action to regulate artificial intelligence before this transformative technology outpaces the rules meant to govern it” — a debate that continues to rage on in Washington and globally.

Bores is viewed as one of the top contenders for the 12th District, which covers a large swath of Manhattan. He’s up against Assemblymember Micah Lasher, Kennedy scion Jack Schlossberg and anti-Trump commentator George Conway, as well as a handful of lesser-known challengers. Public polling has been sparse in the race, and internal polls from earlier this year don’t show a clear front-runner. Madison Fernandez

IN OTHER NEWS

CLOCK’S TICKING: Mamdani has less than a month to fill two longstanding vacancies on the Metropolitan Transportation Authority board — and the appointments could be key for his mission to make the city’s buses “fast and free.” (THE CITY)

NECK AND NECK: Hochul made a joint campaign appearance with Rep. Dan Goldman who’s running for reelection in New York's 10th congressional district, with a primary challenge from Mamdani-backed Brad Lander. (Gothamist)

SARCONE DOGGED: The top prosecutor in the U.S. attorney’s office for the Northern District of New York is accused of misconduct, according to the watchdog organization Campaign for Accountability. (POLITICO Pro)

Missed this morning’s New York Playbook? We forgive you. Read it here.

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