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Sean "Diddy" Combs poses during the MTV Video Music Awards...

Sean "Diddy" Combs poses during the MTV Video Music Awards at the Prudential Center in Newark, New Jersey, on Sept. 12, 2023. Credit: TNS/Angela Weiss/AFP

Manhattan prosecutors produced credit card, hotel and travel records on Tuesday tying Sean "Diddy" Combs’ umbrella company, Bad Boy Worldwide Entertainment, and its subsidiaries to marathon sex binges central to their racketeering and sex trafficking case against him.

Special Agent DeLeassa Penland, an investigator for the U.S. Attorney’s Office, testified for a second day as a summary witness, tying together voluminous evidence presented so far in the sixth week of testimony in the federal case against the hip-hop entrepreneur.

Prosecutors claim he used his vast global enterprise that stretches across the music, liquor and fashion industries to financially and logistically support his sex marathons, which he called "freak-offs." His accountants paid the bills for the hotel rooms and airfare, they say. His company executives handed drugs off to girlfriends for travel and security staff went after romantic rivals and intimidated his victims to prevent them from going to authorities, according to prosecutors.

Combs has pleaded not guilty to the charges, which also include transporting men across state lines for the purpose of prostitution. His attorneys have denied he was involved in any kind of racketeering. They have argued this a case of love and hip-hop, relationships that went through a series of ups and downs, before souring from jealousy and drug use.

WHAT NEWSDAY FOUND

  • Manhattan prosecutors produced credit card, hotel and travel records on Tuesday tying Sean "Diddy" Combs’ umbrella company Bad Boy Worldwide Entertainment and its subsidiaries to marathon sex binges central to their racketeering and sex trafficking case against him.
  • They claim he used his vast global enterprise that stretches across the music, liquor and fashion industries to financially and logistically support his sex marathons, which he called "freak-offs."
  • Combs has pleaded not guilty to the racketeering and sex trafficking case against him.

The alleged women victims involved, Casandra Ventura, a pop singer who performed under the name Cassie, and "Jane," the pseudonym for a single mother who made a living as a model and influencer, were willing participants, defense attorney Teny Geragos told the jurors during opening arguments.

On Tuesday, Penland fielded questions regarding a 30-plus page spreadsheet and timeline that tied limousine trips, flights and hotel room charges to text messages from male escorts to Ventura and Combs.

An Aug. 26, 2009, car service trip to Los Angeles International Airport corresponds with a Virgin America flight for male sex worker Jules Theodore, mentioned earlier in the trial as a regular participant in the sex parties, according to the exhibits shown to the jury. Theodore checked into the London Hotel on West 34th Street in Manhattan where Combs’ assistant had also booked a suite, records show. Penland’s chart showed travel agency fees for the trip and, along with the previously mentioned expenses, charges on Combs’ American Express card. The monthly bill was paid from a Signature Bank account held by 207 Anderson LLC, care of Bad Boy Entertainment.

A Sept. 16, 2014,  stay at the Four Seasons Hotel in Los Angeles corresponded with a flight for male escort Clayton "Dave" Howard from Kennedy Airport to Los Angeles, the agent’s spreadsheet showed. The monthly credit card bill for the alleged "freak-off"  and other expenses came to $307,424 and was paid from five bank accounts, all with ties to Bad Boy.

Some of the hotel bills came with extra expenses, like the $46,786 bill from the InterContinental Hotel in New York for "Petty cash A&G loss and DA penthouse damage" on Oct. 5, 2012.

Earlier in the trial, hotel managers testified Combs often incurred extra fees for cleaning and damaged hotel rooms after his stays.

The jury saw text messages from Kristina Khorram, Combs’ chief of staff, to his personal assistant asking if he was still in the room or had checked out.

Geragos sought to undermine Penland’s testimony, getting her to admit sometimes her spreadsheet did not have complete information and some time frames were off.

Mostly, Geragos replayed text messages from Ventura showing she had an active role in organizing and, seemingly, enjoying the sex parties.

"Me too," she texted Combs ahead of a freak-off. "I just want it to be uncontrollable."

On Monday, prosecutors played a short snippet of video — for the first time in the trial — showing cellphone footage of a freak-off involving Combs and Ventura.

Just before noon on Tuesday, it was the defense team that showed samples of these sex tapes.

The courtroom fell silent as jurors donned headphones and the video feeds in the courthouse and courtroom monitors were turned off. One juror appeared to turn sideways in his chair, appearing to watch his personal TV monitor out of the corner of his eye. Others watched the recordings impassively. Briefly, part of the audio leaked out into the courtroom, muffled voices from a man and woman.

The trial continues Wednesday and prosecutors estimate they will rest their case on Friday.

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