Joel Greenberg enters not guilty plea on latest charges

SEMINOLE COUNTY, Fla. - Former Seminole County Tax Collector Joel Greenberg pleaded not guilty to the latest charges brought against him during an arraigned hearing on Friday.

Greenberg waived his appearance in court on Friday amid speculation that federal prosecutors and Greenberg’s attorney could be hamming out a plea agreement.  The judge ruled he has until May 15 to agree to such a deal. 

Greenberg's attorney says he's not sure if that time frame will work.

"If I get a plea agreement in this case, it’s not something I'm going to sign right away. I have to go over it with my client, and then there’s always some push back in negotiations"

If a plea deal is not met, the case could go to trial.

Greenberg is a political ally and associate of Rep. Matt Gaetz.  Federal prosecutors are examining whether Gaetz and Greenberg paid underage girls or offered them gifts in exchange for sex, the Associated Press reports. Gaetz has denied the allegations and insists he will not resign his seat in Congress.

A plea deal with federal prosecutors could potentially escalate the legal and political jeopardy facing the Florida congressman, signaling that Greenberg could potentially serve as a witness in the Justice Department’s investigation into Gaetz.

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When asked if the recent sex trafficking allegations against Congressman Gaetz could sway his decision on a plea, Greenberg's attorney said of his client, "I think he is uniquely situated."   

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Greenberg’s legal problems began last summer when he was arrested on charges of stalking a political opponent. Greenberg mailed fake letters to his opponent’s school signed by a nonexistent "very concerned student" who alleged the opponent had engaged in sexual misconduct with another student, according to an indictment from last June.

Last August, Greenberg was charged with sex trafficking a girl between ages 14 and 17 and using a state database to look up information about the girl and other people with whom he was engaged in "sugar daddy" relationships, according to an indictment.

He has pleaded not guilty to the charges. Additional charges accusing Greenberg of embezzling $400,000 from the Seminole County Tax Collector’s office were added last month, according to the indictment.

Authorities said he was also caught violating his nightly curfew last month after bonding out because he left Central Florida to see his wife in Jupiter, an incident report revealed.

Greenberg had been scheduled to go to trial in Orlando in June.

U.S. District Judge Gregory Presnell said Thursday that the trial would be pushed back to July if Greenberg is unable to reach a deal with prosecutors by the middle of next month.

Even before his arrest, Greenberg, 36, was a lightning rod for controversy.

He was elected Seminole County’s tax collector in 2016, promising to be a breath of fresh air against an incumbent who had been in office for almost three decades.

Months after taking office in 2017, he started allowing employees to carry guns. In late 2017, he pulled over a driver for speeding while wearing a tax collector badge that resembled a police shield. Local prosecutors declined to file charges of impersonating an officer. Not long after that, Greenberg was pulled over for speeding and asked not to be issued a ticket out of "professional courtesy." The officer declined.

In 2018, Greenberg was widely criticized for posting an anti-Muslim tweet. A year later, the Orlando Sentinel revealed that Greenberg had spent $3.5 million in consultant contracts and salaries to friends and associates, including giving a combined $644,000 to three of his groomsmen and another $677,000 to a campaign adviser.

The Associated Press contributed to this report.