Joel Greenberg to plead guilty, cooperate with investigators in plea agreement

U.S. Rep. Matt Gaetz has been linked to the Greenberg investigation but denies any wrongdoing.
Former Seminole County Tax Collector Joel Greenberg talks to the Orlando Sentinel in a September 2019 interview at his office in Lake Mary.
Former Seminole County Tax Collector Joel Greenberg talks to the Orlando Sentinel in a September 2019 interview at his office in Lake Mary. [ JOE BURBANK/ORLANDO SENTINEL | Orlando Sentinel ]
Published May 14, 2021|Updated May 14, 2021

ORLANDO — Joel Greenberg, Seminole County’s disgraced former tax collector, has agreed to plead guilty to six federal crimes — including sex trafficking of a child — in a deal that calls for him to cooperate with federal investigators, according to a plea agreement released Friday.

The deal, which will be made official during a Monday morning court hearing that Greenberg is required to attend, marks a turning point in the sprawling federal investigation that has roiled Florida politics and reportedly taken aim at Greenberg’s friend and ally U.S. Rep. Matt Gaetz.

Gaetz, R-Fla., has vehemently denied any wrongdoing.

In addition to trafficking, Greenberg will plead to charges of identity theft, stalking, wire fraud and conspiracy to bribe a public official. Prior to striking a deal, he was facing 33 federal charges. Prosecutors will drop the other 27 counts filed against him.

The charges to which Greenberg will admit guilt trace the trajectory of the case, from his initial June 23 arrest for stalking and identity theft, through three subsequent indictments that followed. The agreement revealed Friday sheds new light on some of Greenberg’s alleged misdeeds.

Greenberg admitted to paying more than $70,000 over two years to women for sex, many of whom he met through a website connecting young women, known as “sugar babies,” with older men, called “sugar daddies.”

According to the plea agreement:

Greenberg used at least four accounts to pay the women for sex — including a Tax Collector’s Office American Express card — with the payments typically ranging between $200 and $1,000 and disguised as payments for expenses such as “school,” “food” and “ice cream.”

One of the women Greenberg paid for sex was 17 years old, though Greenberg said she’d claimed to be 18 years old when he first found her through the “sugar babies” website. Greenberg said he initially contacted the minor through a Snapchat account. He paid her $400 for an initial meeting on his boat, in which no sex occurred, and then another $400 to meet at an area hotel where they did have sex.

After that, Greenberg admitted that he would invite the minor — often with others — to meet and have sex at hotels around Central Florida. What’s more, Greenberg said he would often supply ecstasy to attendees — including the minor — and would sometimes pay extra to those who would take the drug.

Greenberg had sex at least seven times with the minor while she was still underage — and also introduced her to adult men who had sex with her, too, though the men aren’t identified in the plea agreement.

Greenberg admitted to frequently — and illegally — using his access to the state’s driver’s license system to “investigate” his sexual partners. And on the afternoon of Sept. 4, 2017, Greenberg ran a search on the minor “because he had reason to believe that the minor was under the age of 18.”

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According to witnesses, Greenberg would also offer women he paid for commercial sex acts the use of driver’s licenses that he obtained from the Tax Collector’s Office.

In addition, after he was first indicted in June 2020 and Greenberg learned that authorities were investigating him for having sex with a minor, Greenberg reached out to her, directly and through a friend, to ask her to lie to investigators about why he’d initially looked up her information in the driver’s license database.

“Greenberg also asked the minor for help in making sure that their stories would line up, because he knew that his commercial sex acts with her were illegal,” according to the plea agreement.

The agreement sheds new light on massive expenditures Greenberg made on Bitcoin, the digital currency, using funds from his office. Prosecutors say he used his public office as a piggy bank, sometimes writing checks for cash that he kept, while other times using office funds as personal loans.

According to the agreement:

On Sept. 20, 2017, Greenberg opened an account in the name of “Seminole County Tax Collector” at Fifth Third Bank, and hid its existence from the chief financial officer for the Tax Collector’s Office. Greenberg “was the sole signatory on the account.”

He then began making small deposits of office resources into the account. For instance, he sold a vehicle owned by the office for $27,000, then deposited the check from that sale at Fifth Third.

That December, he grew bolder, asking the CFO in an email “(H)ow much do we have that can be used for a 60-90 day investment fund (for the Tax Collector’s Office)? What’s the most you can do?” The CFO told him $100,000 was the maximum; Greenberg deposited the check at Fifth Third.

Three days later, on Dec. 29, Greenberg got a cashier’s check from the account payable to himself and deposited it into his personal bank account. From there, he transferred it into an account in his name with a cryptocurrency trading service.

He spent almost all of the $100,000 within five hours on more than 15 cryptocurrency trades. Then, on Jan. 3, he pulled “almost all” of the cryptocurrency he’d bought out of the account.

The money missing from the tax office was causing issues.

“I am sure you saw the email I sent yesterday regarding bills and not much money coming in,” the CFO said in an email to Greenberg during this period. “We are going to need additional funds before the end of the month to get all expenses paid.”

In order to refund the tax office, Greenberg borrowed $90,000 from a family member, deposited it into his personal account, then got a cashier’s check for $100,000, which he marked as “Returned Investment funds.” That was put into an office-owned account.

About a year later, authorities say he pulled a similar scam involving twice as much money.

“(T)here is a fund that I would like to invest in,” Greenberg emailed the CFO on Dec. 12. “How much do we have available that I can allocate to this fund? I was wanting to do between $100k and $200k. It would be a 90 day investment, aiming to yield about 20%.”

A cryptocurrency splurge ensued, followed by yet another entreaty for help from family. Greenberg told a relative in January 2019 that he needed $200,000, explaining he was in “big trouble” for mixing public money with his own. The relative obliged.

But Greenberg didn’t refund his office — he bought more cryptocurrency for himself.

Then, on April 23, 2019, federal agents served a subpoena on the Tax Collector’s Office and Greenberg learned he was under investigation. He went back to the same family member who had given him $200,000 months earlier — asking for the same amount, again.

“When asked what had happened with the other money, Greenberg explained that he had used it to purchase cryptocurrency for himself,” the agreement adds. “Greenberg stated that he would go to jail if he did not pay the $200,000 back to the Tax Collector’s Office.”

As tax collector, Greenberg would take old driver’s licenses turned in by residents and create fake new ones for himself by illegally accessing the DAVID system or the Florida Driver and Vehicle Information Database, according to the plea agreement.

Because the Tax Collector’s Office issues Florida driver’s licenses and identification cards, the state provides certain employees with a DAVID account. However, Greenberg used his access to the DAVID system “to conduct hundreds of unauthorized searches that had nothing to do with any legitimate activities of the Tax Collector’s Office,” according to the plea agreement.

One of the people Greenberg looked up information on was someone named in the plea agreement as R.Z., who Greenberg purchased a boat from in 2015.

Then, in November 2015, Greenberg used R.Z’s personal information that he obtained from the boat purchase to order a replacement driver’s license from the state with R.Z.’s personal information without R.Z.’s knowledge. That fake license with R.Z’s name was mailed to a post office box in Longwood that Greenberg had set up, the agreement states.

Then, on Jan. 3, 2017 — the day he took office as tax collector — Greenberg changed the mailing address for R.Z. from the Longwood post office address back to R.Z’s actual residence.

“R.Z. never authorized Greenberg to obtain a replacement driver’s license using his identity, and R.Z. never knew what Greenberg had done,” according to the plea agreement.

As tax collector in November 2017, Greenberg would then use R.Z.’s personal information from the DAVID system to create a new driver’s license with R.Z.’s name but with Greenberg’s photograph.

Greenberg also used public money from the Tax Collector’s Office to purchase a badge-making machine online. He had the machine shipped to the public office and then used it to create fake driver’s licenses.

When federal agents raided Greenberg’s Heathrow home on June 23, they found the fake driver’s license with R.Z’s personal information and Greenberg’s photograph in his wallet, according to the plea agreement.

But it wasn’t the only time Greenberg used his office to create fake IDs for himself, according to the plea agreement.

In September 2018, a man identified as E.J.C.C. walked into a Tax Collector’s Office to turn in his old driver’s license from Puerto Rico and obtain a new Florida driver’s license.

As part of the office’s procedure, the clerk placed E.J.C.C.’s old license into a basket at the counter. And at the end of the workday, the clerks take their individual baskets and pour out all the old licenses into a main basket behind the counter. Those licenses are then shredded and destroyed about every 45 days.

However, Greenberg grabbed E.J.C.C.’s old Puerto Rico license from the basket before it could be shredded.

Then some time between Sept. 21, 2018, and June 23, 2020, Greenberg used the badge making machine he had purchased, along with card stock and a computer, to produce a fake Puerto Rico driver’s license with E.J.C.C.’s personal information but with Greenberg’s photo, according to the plea agreement.

Federal agents also found that fake license with E.J.C.C.’s information during their raid at Greenberg’s home last June.

Gaetz’s name does not appear in Greenberg’s plea deal, though it’s been widely reported that the former tax collector’s cooperation was sought in order for federal authorities to advance their probe of the Florida congressman.

According to reports, investigators are seeking to determine whether Gaetz had sex with the same 17-year-old Greenberg was accused of trafficking, paid for sex and travel with escorts or traded political favors in medical marijuana legislation for paid sex and other gifts.

Gaetz has said he has never paid for sex or had sex as an adult with someone underage.

If he is found to have had solicited sex with a minor, Gaetz could be prosecuted under the same trafficking law as Greenberg. He also could be charged under the Mann Act, which bans bringing anyone across state or international lines for prostitution, legal experts said.

By the time it was revealed in court last month that Greenberg planned to take a plea deal, he had already met with federal investigators several times and told them about having given women cash and gifts in exchange for sex with himself and Gaetz, according to The New York Times.

According to the report, he decided to talk once he realized the case against him was “overwhelming.”

Greenberg will cooperate fully with the government in the “investigation and prosecution of other persons,” and if his cooperation is of “substantial assistance” to prosecutors, they will recommend lower prison sentence, the agreement says.

Greenberg must register as a sex offender and faces a number of years in prison for each count. He must also pay restitution to several people, including the minor girl and entities like the Seminole County Tax Collector’s Office and the Small Business Administration.

Prosecutors agreed to not charge Greenberg with committing any other federal criminal offense.

But if he knowingly provides incomplete or untruthful testimony, falsely implicates or incriminates someone else or fails to cooperate, Greenberg can be prosecuted for perjury or obstruction of justice, according to the agreement. Prosecutors can also refile the dismissed charges against him.

The agreement said Greenberg will also forfeit at least $654,780 in assets obtained through his offenses.

The plea agreement still must be approved by the judge.