Diddy Paid Off $18 Million Star Island Mortgage To Prepare For $50 Million Get-Out-Of-Jail Bail Proposal

On July 2, a jury found Sean "Diddy" Combs guilty of transporting women across state lines. Crucially, though, the jury acquitted him of the more serious charges of sex trafficking and racketeering conspiracy that could have sent him to prison for life. He now faces up to 20 years in prison. He is scheduled to be sentenced in October.

Diddy, who has been in jail since September 2024, feels he should be allowed to spend the next few months until his sentencing free on bond. And he's putting $50 million on the line to try to make it happen.

According to newly filed court documents, Combs is offering a $50 million bond backed by his sprawling mansion on Miami's ultra-exclusive Star Island. His lawyers argue that he poses no risk to the community, is not a flight risk, and should be allowed to return home under strict conditions, including home detention, private security, and court-approved travel for legal meetings in New York. Oh, and in case his Star Island isn't good enough, he ALSO offered his mom's nearby condo as collateral.

(Photo by David LEFRANC/Gamma-Rapho via Getty Images)

$50 Million Bond

According to his defense team, Diddy's $50 million bail proposal will be:

1. Co-signed by Diddy, his mother, his sister, the mother of his oldest daughter, and his three adult sons.
2. Secured by the equity of his mansion on Star Island.
3. Secured by the equity of his mother's nearby luxury high-rise condo.
4. Diddy's travel will be restricted to the Southern District of Florida, but he would also be allowed to travel to the Southern District of New York for court meetings and doctor visits.

On point #3, Diddy's proposal indicates that the Star Island home was appraised at $48 million and no longer carries a mortgage. According to his bail proposal, at some point in the last year, Diddy paid off the $18 million remaining balance of his mortgage so the home could be used to secure a bond for his release. FYI, there isn't a law that requires a property to be mortgage-free to be used as collateral in a bail bond, but having it fully paid off (legally speaking, "unencumbered") certainly makes it more attractive to the court.

The Star Island Mansion

For those who are not aware, Star Island is an exclusive island in the middle of Miami that has been home to some of the richest and most famous people in the world. With 24/7 security and unobstructed views of the Miami skyline, the island is one of the most coveted — and private — residential enclaves in South Florida.

Located in Biscayne Bay between downtown Miami and South Beach, the man-made island is only accessible by a single gated bridge and features roughly 30 homes. A teardown on Star Island would cost you tens of millions of dollars.

Over the years, Star Island has attracted celebrities like Shaquille O'Neal, Rosie O'Donnell, Gloria and Emilio Estefan, Jennifer Lopez, and billionaire hedge fund manager Ken Griffin.

Diddy owns TWO side-by-side homes on Star Island. He bought his first mansion, a 1.34-acre property with a newly constructed 14,000 square foot home, in 2003. The seller was music mogul Tommy Mottola. In August 2021, Diddy bought the property next door for $35 million. The sellers were Gloria and Emilio Estefan, who continue to own the next home over. Here's a video tour of the home Diddy bought in 2021 for $35 million:

A John, Not a Kingpin

Combs's legal team is arguing that his case is unique. He was technically convicted for violating a law from 1910 called the Mann Act, which his lawyers argue was a vast overreach. The Mann Act (also known as the White-Slave Traffic Act) was originally intended to prosecute those who transported women across state lines for prostitution. His attorneys claim the statute is outdated and has never before been used in circumstances like these.

They describe the sexual encounters at the heart of the case as part of a consensual "swingers lifestyle," and assert that Combs's role, at worst, was akin to that of a "john," not a trafficker or criminal mastermind. They also point to the statute's "racist origins" and its historical misuse to target Black men, most famously heavyweight boxing champion Jack Johnson.

Why the Judge Said No

So far, the court isn't convinced. Judge Arun Subramanian has already denied Combs's release once, citing a pattern of domestic violence and concerns that he poses a danger to others.

During the trial, jurors saw security footage of Combs assaulting former girlfriend Cassie Ventura, and prosecutors presented testimony from another ex, referred to only as "Jane," who alleged a violent altercation even while Combs was under federal investigation. Prosecutors also accused Combs of attempting to tamper with witnesses from inside jail.

In the trial, prosecutors alleged that Diddy ran what amounted to a private criminal enterprise — a secretive, mob-like operation that involved threats, coercion, and abuse. Among the claims aired during the trial were stories of "Freak Offs," ritualized sex acts involving escorts, baby oil, and directed performances while Combs watched and masturbated. The jury was shown video footage of several encounters, which reportedly shocked even seasoned observers in the courtroom.

Combs has remained in the Metropolitan Detention Center in Brooklyn since his arrest last year. His lawyers describe the conditions as "dreadful," and say he faces ongoing threats of violence inside the facility. With sentencing months away, they're hoping the court will reconsider and allow him to spend a few months soaking up some sun on Star Island before whatever happens next…