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Rep. Matt Gaetz’s ‘Wingman’ Joel Greenberg Secures Sentencing Delay After Judge Said He’d Only Postpone for ‘Compelling Circumstances’

Left: Rep. Matt Gaetz (R-Fla.); right: Gaetz's friend Joel Greenberg, via the Seminole County (Fla.) Sheriff's Office.

Rep. Matt Gaetz (R-Fla.) and Gaetz’s friend Joel Greenberg.

The man whom Rep. Matt Gaetz (R-Fla) once described as his “wingman” will be sentenced in his sex trafficking case on Dec. 1, 2022, a federal judge ruled on Friday.

In May 2021, Joel Greenberg pleaded guilty to six of the 33 federal charges of his indictment, including sex trafficking of a child, identity theft, wire fraud and conspiracy. He faces a mandatory 12-year minimum sentence, according to his lawyer. Greenberg has sought multiple adjournments of his sentencing date since that time, citing his ongoing cooperation with the government.

Roughly a year after he reached his plea agreement, Senior U.S. District Judge Gregory A. Presnell indicated that he would not be inclined to postpone his sentencing again beyond this summer.

“Please note that absent compelling circumstances, it is the Court’s intention to set sentencing to be held in August 2022,” Presnell, a Bill Clinton appointee, warned earlier this year on May 16.

That was before Greenberg’s attorney Fritz Scheller sought to file papers under seal touting the extent of his client’s cooperation with federal prosecutors.

“Pursuant to his plea agreement with the Government and to mitigate the significant penalties he faces, Mr. Greenberg has been cooperating with federal prosecutors in active investigations currently being conducted by the United States Attorney’s Office in the Middle District of Florida and the Department of Justice in Washington D.C., as well as in other jurisdictions,” Scheller wrote in a three-page motion on Tuesday. “The unopposed motion to set the date of the sentencing hearing provides confidential information concerning these investigations, as well as information regarding the nature and extent of Mr. Greenberg’s ongoing cooperation.”

That Greenberg’s filing persuaded the judge to grant another adjournment — one that he had been disinclined to provide “absent compelling circumstances” — has intrigued court watchers.

Former federal prosecutor Renato Mariotti noted that the additional four months would not afford enough time for Greenberg to testify in any hypothetical prosecution of Gaetz, who has not been charged with any crime.

“Typically, sentencing dates are not sent until are not set until the cooperation of a defendant is fully complete,” Mariotti noted in a phone interview with Law&Crime. “By that I mean, not just that they’ve provided information to the government, but that they’ve testified that any trials or hearings that the government would require.”

Mariotti pointed to pro-Trump Gen. Michael Flynn’s about-face as an example how it isn’t uncommon for defendants to reverse themselves on a cooperation deal.

The prospect of a future sentencing, Mariotti noted, gives the government “leverage” to compel a defendant to fulfill obligations to cooperate.

Since Gaetz has not faced any charges to date, Mariotti noted that it is “inconceivable” to imagine that prosecutors anticipate that Greenberg will hypothetically testify against the congressman before December.

“It suggests to me either that Matt Gaetz will not be charged, or that Mr. Greenberg will not be needed as to testify at trial of Mr. Gaetz,” Mariotti said. “It doesn’t mean he hasn’t cooperated against Gaetz, but it may be that his cooperation was limited to the production of texts, emails — things like that — or perhaps giving information that authenticated some of that.”

Gaetz reportedly has been under investigation in connection with a 17-year-old girl whom Greenberg paid for sex and provided with narcotics such as ecstasy. Court documents providing the factual basis for Greenberg’s plea state that he paid the minor to “engage in commercial sex acts with him and others.”

The New York Times reported that the Justice Department is scrutinizing whether Gaetz was one of those men.

Gaetz’s lawyer Marc Mukasey, a former law partner of Rudy Giuliani, did not immediately respond to Law&Crime’s email requesting comment on whether he has been apprised of the status of his client’s investigation.

Greenberg’s cooperation reportedly has sparked other activity on the Middle District of Florida’s docket.

Last November, prosecutors indicted Greenberg’s associates Keith Ingersoll and James P. Adamczyk in connection with a multimillion-dollar real estate conspiracy to defraud an unnamed victim out of more than $12 million.

Read the order setting Greenberg’s sentencing here:

[image of Gaetz via Graeme Jennings/Pool/Getty Images; image of Greenberg via the Seminole Co., Fla. Sheriff’s Office]

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Law&Crime's managing editor Adam Klasfeld has spent more than a decade on the legal beat. Previously a reporter for Courthouse News, he has appeared as a guest on NewsNation, NBC, MSNBC, CBS's "Inside Edition," BBC, NPR, PBS, Sky News, and other networks. His reporting on the trial of Ghislaine Maxwell was featured on the Starz and Channel 4 documentary "Who Is Ghislaine Maxwell?" He is the host of Law&Crime podcast "Objections: with Adam Klasfeld."