Former Florida tax collector Joel Greenberg is expected to strike plea deal with prosecutors, attorneys say

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Then- Seminole County tax collector Joel Greenberg talks to the Orlando Sentinel in September 2019, during an interview at his office in Lake Mary, Fla.. - Joe Burbank/Orlando Sentinel/Orlando Sentinel/TNS

ORLANDO, Fla. — Joel Greenberg, the former Seminole County tax collector and associate of U.S. Rep. Matt Gaetz, is expected to plead guilty to criminal charges by the middle of next month, his attorney and prosecutors with the U.S. attorney’s office confirmed during a court hearing Thursday.

The lawyers were given until May 15 to work out the plea deal, otherwise the case will proceed to trial in July. Greenberg had previously been slated to stand trial in June.

“We expect this case to be resolved in a guilty plea,” Assistant U.S. Attorney Roger B. Handberg said during the hearing.

It was not immediately clear to which charges Greenberg would plead guilty to or whether he would agree to testify against anyone as part of the deal. But news that Greenberg is striking a deal with prosecutors is already fueling speculation that he could cooperate in an ongoing probe of Gaetz.

“I am sure Matt Gaetz is not feeling very comfortable today,” Greenberg’s attorney, Fritz Scheller, told reporters after the hearing.

Scheller, however, stopped short of saying whether Greenberg intended to cooperate with federal authorities investigating Gaetz, adding that he had not yet seen a proposed plea agreement from prosecutors and negotiations were in their early stages.

“He’s uniquely situated,” Scheller added, referring to his client. “It’s a complicated case, and there’s a lot of different aspects to it.”

Fritz would not answer questions as to whether Greenberg had any incriminating evidence against Gaetz.

“That goes back to attorney-client privilege,” he said. “I think that if Mr. Greenberg accepts a plea or plea agreement ... It will show a sense of remorse, which he does have, and an acceptance of responsibility.”

Greenberg’s case has drawn national attention in recent weeks after The New York Times reported last week that it had spawned a federal probe into potential sex trafficking offenses by Greenberg’s close friend Gaetz, focused on whether he had a sexual relationship with a 17-year-old girl and paid for her to travel with him.

Later reports indicated that the investigation of Gaetz was also examining whether he and Greenberg had recruited women online and paid them for sex. Gaetz has denied ever having paid anyone for sex.

Federal investigators are also probing an alleged trip to the Bahamas that Gaetz took with former Orlando International Airport board appointee Jason Pirozzolo for potential sex trafficking violations, CBS News reported Wednesday evening.

Gaetz has not been charged with any crime and has denied any wrongdoing.

Greenberg resigned as Seminole tax collector June 24, a day after he was first arrested and charged. He now faces 33 federal charges — including stalking a political opponent, identity theft, wire fraud, bribery, theft of government property, conspiracy to bribe a public official, creating fake IDs using equipment from his public office and sex trafficking of a minor.

He is currently in the Orange County Jail. And Scheller said that Greenberg is in contact with family members.

“He’s safe,” Scheller said. “But it is jail. ... It’s not like he’s listening to Chopin and watching Netflix. ... But his family is a fantastic family. They had no part in this, and they continue to love their son.”

On Friday, Scheller, is scheduled to appear again in federal court for an arraignment on Greenberg’s latest charges in a fourth indictment filed March 30 by federal prosecutors.

Those new charges allege that just days after Greenberg was first arrested and charged in June, he returned home and resurrected a pair of private companies he formed years ago and used those businesses to obtain more than $432,000 in fraudulent loans through a federal program designed to help small companies struggling during the COVID-19 pandemic shutdown.

In the latest indictment, prosecutors also allege that Greenberg obtained those loans by bribing a federal employee with the Small Business Administration.

Charges also allege that Greenberg as Seminole’s tax collector diverted more than $400,000 in public money to private accounts to purchase digital currencies and buy himself personal items, including autographed memorabilia of basketball players Michael Jordan and Kobe Bryant.