Diddy Keeps Earning Millions, Even While He Serves Prison Time

Sean “Diddy” Combs may be behind bars, but one of his most prized assets is still clocking impressive revenue. Earlier this year, the music mogul was convicted and sentenced to 50 months in prison, along with a $500,000 fine. Despite that setback, Diddy luxurious Gulfstream G550, aptly named LoveAir, is still flying high.

According to reporting from The U.S. Sun, the jet has earned roughly $4 million in just eight months while under the management of a high-end charter company. It’s a lucrative reminder that in private aviation, assets continue to work even when their owners can’t.

How Private Jets Make Money

Industry insiders told Jettly that aircraft owners don’t need a $60 million plane to generate passive income. The key requirement is ensuring the aircraft is operated under a licensed air carrier, known in the U.S. as a Part 135 operator. Once vetted, jets are listed on charter platforms where brokers match them with clients. Passengers often never know who the real owner is.

That appears to be the case with Diddy Combs G550, one of the most sought-after models for long-haul luxury travel. With powerful engines, intercontinental range, plush seating, and a full-size galley, the aircraft offers a seamless long-distance experience. Its performance and comfort make it a favorite among charter clients.

Who Books Private Jets?

Private jet travel isn’t limited to billionaires. Corporations, business executives, wealthy individuals, and even vacation groups regularly charter aircraft for flexibility, privacy, and convenience. For many, bypassing security lines, flying on their own schedule, and accessing smaller airports are worth the premium price.

Major brokers allow travelers to choose aircraft based on distance, budget, group size, and comfort needs—meaning anyone with the means can book anything from a small turboprop to a Gulfstream G550.

Private aviation continues to expand, with an estimated 23,000 to 23,500 private jets worldwide. Between 60% and 70% of them fly out of North America, and the global fleet grows by several hundred aircraft each year.

For Combs, the earnings from LoveAir offer a rare bright spot during a difficult chapter. Though the mogul can’t enjoy his jet personally, its continued demand underscores a broader reality: in private aviation, the right investment can keep paying dividends—no matter where the owner is.