Diddy making millions on side hustle while in jail

The 3rd week of the trial will resume on Tuesday, May 27, after Memorial Day
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Photo credit: Shutterstock.com / Kathy Hutchins

Even though Sean “Diddy” Combs has been locked up for the past eight months, he still manages to make millions from behind bars.

Diddy, the owner of a $60 million luxury private jet, has been reportedly renting the plane out to unsuspecting customers who don’t know he is the owner. The jet and the high-end service are under Diddy’s company, LoveAir LLC.


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Diddy changed his name again to “Brother Love” in 2017

Most casual observers of music and pop culture are blissfully unaware that Diddy changed his nickname again to “Love.”  Actually, Diddy began calling himself “Love, a.k.a. Brother Love” in November 2017. While the Bad Boy boss initially joked about it, he later legally changed his middle name to “Love” in 2021, becoming Sean Love Combs.

Diddy’s Gulfstream G500 has flown over 100 flyers

More than 126 wealthy clients have rented Diddy’s Gulfstream G550 since he was indicted and arrested in September 2024 and have logged nearly 150,000 miles in the air, bringing about $4 million into his coffers.


Luxury operator Silver Air has been renting out the plane, and customers spend an average $32,597 per 1,186-mile journey, according to the US Sun. 

The revenue stream generated from these luxury flights has replaced some of the expenditures for Diddy’s legal defense, which has cost approximately $10 million so far.

The newspaper describes the Gulfstream jet as a jet-black long-range aircraft that can carry up to 14 passengers in opulent 7’3″ by 43’11” cabins, with a maximum range of 6,500 nautical miles. The website reveals the jet’s upscale oak-colored interior with large padded couches and chairs that boast ample leg space. 

Diddy needs the income generated from the flights

Diddy, 55, can use the income since he was once worth nearly a billion dollars before it shriveled almost overnight. This, of course, was before this sex scandal detonated in November 2023 after Casandra “Cassie” Ventura Fine filed a civil lawsuit against Diddy.

In the immediate aftermath, a nonstop parade of civil lawsuits was filed that made similar claims that Cassie had accused Diddy of committing. The mushrooming scandal caught the attention of the U.S. Department of Justice, particularly on the suspicion of interstate travel for the purpose of prostitution as well as alleged sex trafficking.

Diddy’s devastating downfall was accelerated when CNN aired an old video showing Diddy beating, kicking and dragging Cassie in a ritzy hotel exactly one year ago. Four months later, Diddy was apprehended by federal agents and housed at the infamous Metropolitan Detention Center in Brooklyn, New York.

Prosecutors accuse Diddy of committing a myriad of felonies

During the Department of Justice’s opening statement at the sex trafficking trial, U.S. Attorney Emily Johnson told jurors to brace themselves because they would hear from victims who “will tell you about some of the most painful experiences of their lives.”

Continuing, Johnson said “During this trial, you are going to hear about 20 years of the defendant’s crimes… But he didn’t do it alone; he had an inner circle of bodyguards and high-ranking employees who helped him commit crimes and helped him cover them up.

“Kidnapping, arson, drugs, sex crimes, bribery and obstruction. These are just some of the crimes the defendant and his inner circle committed again and again.”

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Terry Shropshire
A veteran of the U.S. Air Force and Buckeye State native, Terry has also written for the Atlanta Journal-Constitution, the Atlanta Business Chronicle and the Detroit Free Press. He is a lover of words, photography, sports, books, travel, and THEE Ohio State Buckeyes. #GoBucks
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