Sean 'Diddy' Combs' ex-employee details setting up hotels for rapper's 'Freak-Offs'
Share and Follow

George Kaplan, testifying in court on Wednesday, revealed that during his employment with Sean “Diddy” Combs from 2013 to 2015, one of his recurring responsibilities was organizing the hotel accommodations for the rap mogul’s “Freak-Offs.”

Kaplan recalled that he frequently found himself arranging the hotel stays where these events curated by Combs occurred, shedding light on this aspect of his former job.

The former assistant said he was initially hired to grab Combs, 55, food, toiletries or other household items he may need, but his role changed over time because his boss “trusted [him] a bit more.”

Kaplan testified in Manhattan federal court that one day he was given a bag with Combs’ personal belongings inside of it, including clothes, a speaker, liquor, baby oil and Astroglide.

He then had to restock the same supplies using a Combs Enterprises corporate credit card.

Kaplan testified that he would call up hotels just hours in advance to book a room for Combs under the pseudonym “Frank Black” in cities like New York, Los Angeles or Miami.

He noted that some of the Bad Boy Records founder’s favorite spots to stay were the Trump Hotel in Columbus Circle, the SLS in South Beach and the InterContinental in Los Angeles. (Combs was infamously caught on camera beating up his ex-girlfriend Cassie Ventura in 2016 at the now-closed InterContinental hotel in Century City, Calif.)

Ventura, 37, testified last week that the “Last Night” rapper introduced her to “Freak-Offs” at age 22 and that Combs viewed the acts as “voyeurism,” or when person gets turned on by watching others have sex.

She also claimed the “Freak-Offs” would happen weekly and the longest one lasted up to about four days.

The drug-fueled romps consisted of Ventura and an escort engaging in sexual behavior with their bodies all “glistening” with baby oil, while Combs watched in a nearby corner and masturbated.

Ventura claimed she suffered medical issues as a result of the acts, including stomach problems, “frequent” urinary tract infections and sores on her tongue and mouth.

After the “Freak-Offs” ended, Kaplan testified that he had to help clean up the hotel rooms, removing a lot Gatorade bottles, liquor bottles and baby oil bottles, so that hotel staff’s eyebrows would not be raised.

Kaplan testified he had become aware that hotels would often sell images or videos to “embarrass” public figures and that was something he “wanted to avoid.”

“There was a single occasion where I came across some brown crystalized powder and I didn’t know what it was and I got rid of it,” he claimed.

Later in his testimony, Kaplan also claimed he would have to pick up drugs for Combs. The government has provided him with immunity so that he could fully testify without fear of criminal retribution.

“I did what he asked me to do,” the former executive assistant said on the stand.

Kaplan testified that he would often work 80 to 100 hours a week and shifts could end as late as 7 in the morning. He was paid $125,000 for the first year of his services.

The ex-assistant claimed that despite becoming a trusted worker for the “I Need a Girl” rapper over time, Combs would make “monthly threats” that he could lose his job.

Kaplan claimed his then-boss told him he only wanted to “be surrounded by the best and [that] those around him at the time were not performing at that level.”

The feds have charged Combs with racketeering, claiming he used Combs Enterprise to carry out illegal activities. He has also been charged with sex-trafficking and transportation to engage in prostitution.

The “Bad Boy for Life” rapper has denied all wrongdoing and pleaded not guilty.

If you or someone you know is affected by any of the issues raised in this story, call the National Domestic Violence Hotline at 1-800-799-SAFE (7233) or text START to 88788.

If you or someone you know is affected by any of the issues raised in this story, call the Sexual Assault Hotline at 1-800-330-0226.

Share and Follow
You May Also Like
Jesus Martinez charged with setting CTA Blue Line fire near Damen Blue Line stop in Wicker Park: Chicago Police Department

Chicago Police Department Charges Jesus Martinez in CTA Blue Line Arson Near Damen Station in Wicker Park

A man has been charged after allegedly igniting a fire on a…
US Coast Guard pursues third 'dark fleet' oil tanker as Trump targets Venezuelan sanctions evasion network

US Coast Guard Intensifies Crackdown on ‘Dark Fleet’ Oil Tankers Amid Trump’s Push Against Venezuelan Sanctions Evasion

The U.S. Coast Guard is currently tracking a sanctioned oil tanker near…
FILE - Colorado Gov. Jared Polis speaks to the National Governors Association at the Broadmoor Hotel in Colorado Springs, Colo., July 25, 2025. (AP Photo/David Zalubowski, File)

Colorado Governor Criticizes Trump for Denying Disaster Requests Amid Political Tensions

DENVER (AP) — Colorado Governor Jared Polis has criticized President Donald Trump…
Internet slow? Map reveals which provider is fastest at every Alabama address

Discover Alabama’s Fastest Internet Provider: Unveiling the Ultimate Speed Map for Your Address

(NEXSTAR) – If you’re constantly dealing with web pages failing to load…
Family speak out after doctor's body found in Dollar Store freezer

Heartbreaking Discovery: Family Breaks Silence on Doctor Found in Dollar Store Freezer

The family of Dr. Helen Massiell Garay Sanchez, an aspiring physician, is…
Israeli diaspora minister says Australia should have seen 'writing on the wall' before terror attack

Israeli Minister Criticizes Australia’s Oversight Before Terror Attack: Calls for Proactive Measures

Amidst the tragic aftermath of a terror attack that claimed 15 lives…
Former classmate says suspect in Brown, MIT killings was ‘socially awkward’ and ‘angry’ during college years

Former Classmate Describes Brown and MIT Murder Suspect as ‘Socially Awkward’ and ‘Angry’ During College Years

A former schoolmate of the alleged shooter involved in the tragic Brown…
Chicago holiday travelers: Thousands of travelers going through O'Hare, Midway airports, roads as Christmas travel rush begins

Chicago’s O’Hare and Midway Brace for Massive Holiday Travel Surge as Christmas Rush Kicks Off

CHICAGO (WLS) — As the festive season approaches, throngs of travelers hit…