Jonathan Oddi

Jonathan Oddi is a former adult-film performer and male escort who, in a recorded police interview on May 20, 2018 — two days after he opened fire on officers inside the lobby of the Trump National Doral golf resort in Miami — told investigators he had a years-long sexual relationship with Sean "Diddy" Combs and Combs's then-girlfriend Cassandra "Cassie" Ventura, describing himself as their "sex slave." He said the arrangement included roughly fifteen paid encounters, that Combs directed and watched the sessions, and that he had separately been paid a multimillion-dollar settlement to stay silent about it. At the time, his account was treated as the incoherent claims of a man in the middle of a mental-health crisis and was not investigated. It resurfaced seven years later during Combs's 2025 federal sex-trafficking trial, when Ventura — without knowing Oddi had already made these claims on video in 2018 — independently identified him by name and photograph in her own testimony and confirmed several of the specific details he had described to police.

Background

Oddi was 42 years old at the time of his 2018 arrest (reported as 49 in 2025 coverage) and worked in adult entertainment and, later, as a self-employed fitness trainer. Court filings from his 2014 divorce, cited by NBC 6 South Florida, show he reported a net worth of negative $1,800 in August 2014 and monthly income of about $2,000. Less than a month later — between September 5 and October 30, 2014 — he paid cash (no mortgages) for five distressed properties totaling $765,300, three Homestead, Florida condos and a Bayshore Drive unit in Miami, through an entity called Oddi Investments LLC; he resold them within two years for a combined $934,000. NBC 6's contemporaneous 2018 reporting could not identify where the cash came from and posed the question directly: "So where did a fitness trainer who was worse than flat-broke in August 2014 acquire enough cash in September 2014 to start buying properties?" That reporting predates any public connection between Oddi and Combs by six years, and the timing lines up with the July 2014 settlement date discussed below.

The May 2018 Trump National Doral Shooting

Shortly after 1:30 a.m. on Friday, May 18, 2018, Oddi jumped a fence onto the golf course at the Trump National Doral Miami resort, spent roughly two hours on the property, then entered the main clubhouse lobby carrying an American flag and a Glock 17 handgun. He fired shots into the ceiling and chandelier, broke electronics at the front desk, and, according to the Miami-Dade State Attorney's closeout report, pointed his weapon toward arriving officers before an exchange of gunfire. Five officers discharged their weapons — Sgt. Luis Celis, Officer Albert Tellez, Officer Scott Demby and Officer Rafael Cuan of the Doral Police Department, and Officer Joseph Azrak of the Miami-Dade Police Department. Oddi was shot in both legs and was found hiding near a third-floor elevator. He was hospitalized for three days at Kendall Regional Medical Center before being booked into the Miami-Dade County jail.

The Miami-Dade State Attorney's Office (Katherine Fernandez Rundle) filed formal charges on June 8, 2018 covering roughly a dozen felony counts, including five counts of attempted second-degree murder of a law enforcement officer, armed burglary, aggravated assault with a firearm, and grand theft. A judge set bond at $4 million on the attempted-murder counts and ordered him held without bond on two of the remaining charges. Separately, in an April 8, 2019 closeout memorandum (SAO Case #62/18/05/18/005, based on FDLE Case #MI-27-0085), the State Attorney's office concluded the responding officers were legally justified in using deadly force and that no charges would be filed against them. That closeout report does not resolve Oddi's own prosecution; as of mid-2025, he remained in Miami-Dade County custody awaiting trial on the 2018 charges. No docket/case number could be independently located for that pending Florida criminal case — Miami-Dade's online case search was not accessible for automated lookup — so no case record has been added to this site's case database for it.

The Police Interview and the Interrogation Video

The State Attorney's closeout report is itself a primary source that Combs came up almost immediately. It records that on the night of the shooting, at the hospital, MDPD Homicide Detective Christopher Perez told an FDLE agent that Oddi "stated that he had a settlement with the former President of the United States, current President of the United States, and P. Diddy" — a detail preserved in an official law-enforcement report years before any media outlet connected Oddi to Combs.

Two days later, on May 20, 2018, FDLE Special Agent Alberto Borges formally interviewed Oddi — Mirandized, without an attorney present — at the MDPD Homicide Office; Detective Oscar Andino was also present, and the interview was video recorded. The portion of that recorded interaction that later circulated publicly (uploaded to YouTube in October 2020 as "Interrogation of Trump Doral Shooter Jonathan Oddi") shows Oddi telling officers, on camera, "I was like a sex slave, OK? For them, that's what I was," and describing roughly fifteen sexual encounters with Combs and Ventura in which Combs allegedly directed and watched. According to later reporting (TMZ, NewsNation), investigators and the officers on the video did not pursue or credit the claims at the time, treating them as consistent with the same erratic, "premeditated" political rant that had led to the shooting rather than as a real allegation — Combs was not a public figure in any sex-trafficking investigation in 2018, and Oddi's account had no corroboration. The video embedded below is that footage.

The Alleged $5 Million Settlement and NDA

Oddi has said the sexual relationship ended around 2014 with a payout in exchange for his silence. A document reported by the Daily Mail to be a non-disclosure agreement between Oddi and Combs, dated July 9, 2014 and bearing a signature attributed to Combs, surfaced in 2025 reporting; multiple outlets that reviewed the coverage (Distractify, HotNewHipHop, AOL, Cinemablend, among others) describe the figure as $5 million. Oddi's ex-wife, attorney Tonia Troutwine — married to Oddi for six years, into the 2014 period — has publicly confirmed the NDA's existence and said its timing lines up with their divorce. She has also said Combs was "scared" of Oddi and that the relationship with Combs and Ventura marked the start of a personal decline for Oddi, who she says had no history of drugs or alcohol before it. The authenticity of the signature on the document has not been independently established in any reporting.

In the interrogation video itself, Oddi names two attorneys in connection with the alleged payoff: Mark Geragos and "Kenny" -- referring to Kenneth Meiselas, Combs's longtime entertainment attorney of over 20 years (name partner, Grubman Shire Meiselas & Sacks, which dropped Combs as a client in June 2024). Some secondary coverage of Oddi's claims has misattributed the second name to Meiselas's son, Ben Meiselas -- a former Bad Boy Entertainment intern turned attorney, now far better known as a co-founder and host of the progressive media network MeidasTouch -- but Oddi refers to the father, not the son, on the recording.

The NBC 6 financial reporting described above — an unexplained cash-property-buying spree that began in September 2014, two months after the NDA's stated date, reported in 2018 with no knowledge of any Combs connection — is independent, contemporaneous circumstantial corroboration that a real payment of some kind occurred around that time, even though it does not by itself establish the amount, source, or full nature of Oddi's account.

Vindication at the 2025 Federal Trial

Cassie Ventura testified in Combs's federal trial (United States v. Combs, No. 1:24-cr-00542, S.D.N.Y.) beginning May 13, 2025. During that testimony she identified "Jonathan," a male escort "frequently used in Miami," and was shown a photograph of Oddi, whom she confirmed by name. She testified the couple stopped using Oddi after she discovered he had secretly recorded one of their encounters — which matches what Oddi had told police in 2018, years before Ventura's account became public. On cross-examination, the defense played an audio recording, which Ventura confirmed was authentic, of her threatening Oddi over the recording: "If you have it pull it up or I will kill you, and he will kill you again," and "If you don't show me, I will cut you. Cut you up!" Defense counsel also noted that Combs had "spent a great deal of time [and] money to make sure that that video went away" — consistent with Oddi's own account of a settlement. Coverage of the trial (Rolling Stone, TMZ) described the moment as effectively vindicating claims about Oddi that had been dismissed as implausible in 2018.

Current Status

As of 2025, Oddi remained incarcerated in Miami-Dade County on the 2018 Trump National Doral charges, separate from and predating any involvement in the Combs matter. He has not filed, and has not been reported to have filed, any lawsuit against Combs; his connection to the Combs litigation is as a person named in Ventura's testimony and in his own earlier statements to police, not as a party to any case. No new case record has therefore been added to this site's case database for him — see the note above regarding his own pending Florida criminal matter, for which a docket number could not be independently located.

Sources

  • Office of the Miami-Dade State Attorney (Katherine Fernandez Rundle), Police Shooting Closeout Memorandum, SAO Case #62/18/05/18/005 (Apr. 8, 2019) — miamisao.com
  • ShockYa, coverage naming Mark Geragos and a Meiselas in connection with Oddi's payoff account (2025) — tabloid-tier sourcing, some of which misattributes the Meiselas reference to Ben rather than Kenny — shockya.com
  • Variety, "Attorney Ben Meiselas on Repping Colin Kaepernick, Interning for Diddy and Hillary Clinton" (2019) — variety.com
  • NPR, "Police Subdue Man After He Fires Shots In Lobby Of Trump Club In Florida" (May 18, 2018) — npr.org
  • NBC 6 South Florida, "Florida Man Who Stormed Trump's Doral Resort is Formally Charged" (June 8, 2018) — nbcmiami.com
  • NBC 6 South Florida, "Alleged Trump Doral Gunman Jonathan Oddi Went From Dead Broke to Property Buying Spree in One Month" (2018) — nbcmiami.com
  • CBS12 / WPEC, "Suspect in shooting at Trump National held without bond" (2018) — cbs12.com
  • WPTV, "Man shot by cops after Trump Doral confrontation, out of hospital, booked into jail" (2018) — wptv.com
  • Union Leader, "Who is Jonathan Oddi, the man shot after ranting and firing shots at Trump National Doral?" — unionleader.com
  • NewsNation (Ashleigh Banfield), "Diddy paid me for sex: Trump hotel shooter" (2025) — newsnationnow.com
  • Yahoo News, "The ex porn star who shot up Trump's hotel and made wild Diddy claims breaks silence" (2025) — yahoo.com
  • Rolling Stone, "Sean Combs Trial: Cassie Testifies, Baby Oil, Imprisoned Male Escorts" (May 2025) — rollingstone.com
  • TMZ, "Diddy 'Sex Slave' Vindicated by Cassie Testimony" (May 16, 2025) — tmz.com
  • Distractify, "Ex-Porn Star Jonathan Oddi Claims Diddy Kept Him as a Sex Slave and He Signed a $5 Million NDA" (2025) — distractify.com
  • HotNewHipHop, "Man Who Claimed To Be Diddy's Sex Slave After Donald Trump Golf Course Shooting Has An Alleged NDA With The Rapper" (2025) — hotnewhiphop.com
  • AOL (crediting Daily Mail), "Ex-porn star who shot up Trump resort — and claimed to be Diddy sex slave — signed NDA with rapper in exchange for $5M: bombshell report" (2025) — aol.com
  • Yahoo News, "Ex-Wife Of Diddy's 'Sex Slave' Speaks Out, Accuses Rapper Of 'Destroying' His Life Amid Sex-Crimes Trial" (2025) — yahoo.com
  • Yahoo News, "Federal Prosecutors Shock Court In Diddy's Trial With Revelation About A Missing Key Witness" (2025, includes Oddi/NDA section) — yahoo.com
  • YouTube, "Interrogation of Trump Doral Shooter Jonathan Oddi" (uploaded Oct. 29, 2020) — the interrogation video embedded above — youtube.com
  • United States v. Combs, No. 1:24-cr-00542 (S.D.N.Y.), Cassie Ventura testimony, May 13-16, 2025 (via case docket already on file in this database)