It’s Even Weirder Than You Thought: How a Roger Stone Acolyte and a ‘Tiger King Tax Collector’ Spawned the Matt Gaetz Scandal

This is what happens when you give Florida Man internet access.

Rep. Matt Gaetz (R-FL) has long had a special skill for getting his name in headlines, but he must be wishing he could have been left out of recent stories about his friend, former Seminole County tax collector Joel Greenberg, being indicted for a laundry list of federal charges, including underage sex trafficking.

In the perennially weird state of Florida, there’s often more to a story, and this one is no exception. Mediaite has obtained new information explaining how this scandal originally unfolded — and how it ties in to a Central Florida blogger and several other notable Sunshine State politicos.

Greenberg is currently in jail, facing 33 counts in a federal indictment that’s been amended four times so far. The charges against him have potential sentences that would keep him behind bars until he is a very old man. He is reportedly cooperating with prosecutors in exchange for a lighter sentence — a move which many observers are interpreting as highly dangerous for Gaetz and others in Greenberg’s inner circle. Multiple media outlets have reported that Greenberg has been talking with federal investigators since last year, and the U.S. Marshals moved him out of the Seminole County jail and into their custody in March shortly after he was re-arrested for violating the curfew rules of his pre-trial release, lending further credence to the theory he is working with the feds.

From reform candidate to rule-breaking elected official 

Here’s how this mess all started: Joel Greenberg made his first foray into elected office in 2016 as a self-funded candidate, defeating the incumbent tax collector in Seminole County, located northeast of Orlando. His father, Andrew Greenberg, founded the Greenberg Dental chain in the 1980s; the company now has nearly 100 locations across Florida and has made the family independently wealthy.

On the financial disclosure forms Florida law mandates for elected officials, Greenberg listed his personal net worth as nearly $5.9 million at the end of 2019, including $5.5 million of stock in the family business AWG Inc., $276,000 in bank accounts, and $85,500 in jewelry.

Greenberg’s first and only term was marred by controversies beginning shortly after he was sworn in. He had campaigned as a reformer and some of his initiatives, like an updated website and significant reductions in wait times for services like driver’s license renewals, were welcomed as long overdue. Other reforms ruffled feathers and triggered reporters and investigators to start sniffing around. Many of these items were revealed in an October 2020 audit of the tax collector’s office during Greenberg’s tenure, that was conducted after he was arrested:

• He allegedly spent tens of thousands of dollars to set up the tax collector’s office to be able to accept Bitcoin payments, a reform he touted as the way of the future but was used by very few Seminole County residents, and criticized as hardly worth the cost.
• Another $90,000 was allegedly spent to build and install server equipment that was apparently to be used for bitcoin mining. The equipment wasn’t properly installed or operated, however, and overheated, causing nearly $7,000 in damage that wasn’t covered by insurance.
• He allegedly hired a contractor for $15,000 to install sprinkler heads on office property that could be operated remotely and pointed at petitioner groups gathering signatures for ballot issues he opposed (Florida law has a broad list of opportunities for citizen petitions to affect local and state law, and even amend the state constitution).
• He allegedly purchased firearms, body armor, and badges for himself and his senior office staff, essentially creating a security force for the tax collector’s office. Former Florida Attorney General Pam Bondi, a Republican and fellow Trump supporter, criticized this as improper. Greenberg was accused of impersonating a police officer after he flashed his self-issued badge to pull over a woman for speeding.
• There were nearly $400,000 in questionable credit card charges, many of which were made on weekends or after hours. Some of these credit card charges are reportedly connected to $900 in Venmo payments that Greenberg made to young women, allegedly for sex, shortly after Gaetz sent Greenberg that exact amount, also over Venmo. (Late breaking reporting by The Daily Beast has more details on those Venmo payments, totaling thousands of dollars, including at least one made to a woman who was only 17 years old at the time.)

Greenberg was also accused of soliciting the son of one of his employees to hack the county computer system and hold it for a ransom worth half a million dollars in Bitcoin. There’s a creepy voicemail he and Gaetz left for State Rep. Anna Eskamani in 2019. He’s also accused of using government funds to buy autographed Kobe Bryant and Michael Jordan memorabilia, submitting fraudulent paperwork to obtain Paycheck Protection Program funds from the Small Business Administration, and so on and so on…

Bottom line, there was an absolute deluge of news stories criticizing Greenberg for coloring far, far outside the lines regarding what his office’s purposes and powers legally were, for allegedly spending taxpayer funds to benefit himself and to grant lucrative consulting contracts to his friends, and for just in general acting “like the Tiger King got elected tax collector,” as a recent New York Times headline described him.

But it was Greenberg’s alleged scheme to smear the reputation of Brian Beute, one of his 2020 Republican primary opponents, that dropped a metaphorical nuclear bomb on all his ambitions, and turned what was initially a local political corruption story into one that may very well implicate Gaetz and other powerful Florida Republicans.

A scurrilous — and pointless — attack against a primary opponent 

Beute is a music teacher at Trinity Preparatory School, an exclusive private school in Orlando where tuition for the upcoming 2021-2022 school year for students grades 6 through 12 is nearly $25,000. He’s also a Seminole County resident, a lifelong Republican, and was a vocal opponent of the River Cross development project backed by Chris Dorworth, a real estate developer, lobbyist, and former legislator — and friend of both Gaetz and Greenberg. (Dorworth abruptly resigned from his lobbying firm last week, saying that he didn’t want recent press reports to be a distraction for their work.)

The River Cross project — a proposed shopping and residential complex to be constructed in a rural section of eastern Seminole County — was defeated, and Beute was inspired by his experience helping lead that effort to run for office himself, filing to challenge Greenberg for the Republican primary in 2020.

Beute, according to numerous well-connected observers of Central Florida politics, never stood a chance of defeating Greenberg, who despite his controversies, had high name recognition and personal wealth he could pour into a campaign to drown out any opponents. Even after Greenberg was arrested, resigned from office, and dropped his re-election bid, Beute still lost the primary by nearly 12 points to J.R. Kroll, who would go on to win the general election and is the current Seminole County Tax Collector.

A source with knowledge of Greenberg’s campaign operations who spoke to Mediaite on the condition of anonymity confirmed that Greenberg’s internal polling showed him easily trouncing Beute, but Greenberg was still “fixated” on defeating him, presumably at least in part due to Beute’s successful opposition to Dorworth’s project. Another source familiar with Greenberg’s campaign said that he was advised to just ignore Beute and keep his head down until after the primary, advice which he unwisely ignored.

According to the federal indictment against Greenberg, he created fake social media profiles impersonating Beute and others in an attempt to attack Beute’s reputation. A Twitter account pretending to be Beute made posts supporting segregation and white supremacy. A Facebook account was created, pretending to be another teacher at Trinity Prep, falsely accusing Beute of  sexual misconduct with an underage male student. Letters were sent to the headmaster at Trinity Prep, pretending to be from a student and also making the same false accusations of sexual misconduct.

Greenberg’s fingerprints and DNA were found on the letters and investigators also traced some of the online attacks back to an IP address at Greenberg’s residence.

But Greenberg didn’t act alone in his alleged attempt to smear Beute. He had help from a local Central Florida blogger.

Following in the footsteps of Roger Stone

Jacob Engels is a Republican activist who runs a right-wing blog called “Central Florida Post.” He’s long been associated with self-proclaimed “dirty trickster” Roger Stone, an adviser to former President Donald Trump who was convicted of seven counts of lying to Congress and the FBI and witness tampering, and sentenced to forty months in prison. Stone was due to report to prison last July, but Trump commuted his sentence and later issued Stone a pardon during the final weeks of his presidency.

Engels has called Stone his mentor, and at a federal hearing on February 23, 2019, Stone testified that Engels was one of a handful of associates he had entrusted to assist with his social media posts, granting Engels access to his Instagram and other accounts. Engels has appeared on Stone’s program on conspiracy theorist Alex Jones’ InfoWars network, and has written multiple articles defending Stone on the pro-Trump website The Gateway Pundit.

He denies having official membership in the Proud Boys, but Engels also has numerous connections to the extremist group that Stone has habitually hired as bodyguards and who have been implicated in the Jan. 6 riot at the U.S. Capitol. Engels has repeatedly been photographed at Proud Boy events and wearing their distinctive black-and-gold polo shirt uniform. A February 2019 Daily Beast article, “Meet Jacob Engels, Roger Stone’s Mini-Me,” details Engels’ background, connections to Stone, and appearance at protests at the Broward County Supervisor of Elections office after the 2018 elections — along with members of the Proud Boys and Gaetz himself.

Engels’ modus operandi for his Central Florida Post site has followed a Roger Stone-like pattern of attacking his political foes and promoting his allies. He’s frequently been accused of not letting pesky things like truth and facts get in the way of his political narrative; a November 27, 2018 Orlando Weekly article on Engels’ activities noted that their reporter “did not reach out to Engels for this story because he lies every single time we attempt to have a correspondence with him.”

During the past few years, Engels published multiple fawning articles about Greenberg, as well as at least two Facebook Live videos attacking Beute — with highly suspicious timing.

A source with knowledge of the investigations into Greenberg told Mediaite that it is believed that Engels is the unindicted co-conspirator mentioned in the federal charges for stalking and harassing Beute. Besides the articles promoting Greenberg and his allies, Engels was also captured in the background of a video clip that’s been circulating again as this scandal has attracted national media attention. At approximately the one minute mark in the below clip from The Situation Room with Wolf Blitzer, Engels is wearing a pink polo shirt, standing behind Greenberg at the Seminole County Tax Collector’s Office while he was being interviewed by FloridaPolitics.com reporter Scott Powers (the man to the right of Engels).

Greenberg never declared any expenditures paid to Engels for his promotional work on his campaign finance reports, but considering all the other financial shenanigans in this sordid tale, that doesn’t mean that Greenberg or someone else weren’t compensating Engels in some way.

When Facebook and Instagram permanently banned Stone’s accounts and those of many of his associates last July for “coordinated inauthentic behavior,” Engels and the Central Florida Post were caught up in the purge, which encompassed 54 Facebook accounts, 50 Facebook pages, and four Instagram accounts. Among the coordinated posts cited by Facebook’s director of security policy were ones regarding “a Florida land and water resources bill,” possibly meaning Dorworth’s River Cross development, which Engels had supported. Engels was also banned from Twitter around the same time.

Before he was excommunicated from most of his social media, Engels posted Facebook Live videos attacking Beute on June 15 and June 20, 2020. These videos were removed when Facebook banned Engels’ accounts, but not before they were downloaded; these video files were provided to Mediaite and are posted below.

At the time these videos were posted, no one had knowledge of the content of the letters Greenberg allegedly sent to Trinity Prep except the school, the Seminole County Sheriff’s Office, federal agents investigating the case, Beute, and his attorney. Well, no one except the sender of the letters.

And yet here was Engels, openly accusing “Creepy Brian Beute” of being “mentally ill” and committing sexual improprieties with underage students. In both videos, Engels makes multiple references to Beute, a music teacher, “trom-boning” his students.

“Creepy Brian Beute who was involved in some tromboning incident over at Trinity Prep as a teacher, tromboning, you know we don’t know what he was tromboning, but we heard there was a tromboning incident,” said Engels in the June 20, 2020 video.

June 15, 2020 Central Florida Post Facebook video:

June 20, 2020 Central Florida Post Facebook video:

Engels also repeatedly threatened Beute in the videos and in comments on the original Facebook posts that Beute shouldn’t criticize Engels or his site ever again, Beute “needs to drop out” of the race, and vowing that Central Florida Post would “publish the results of our work” before the Republican primary.

There is another even earlier tie between Engels and the defamatory letters attacking Beute that were sent to Trinity Prep. On October 29, 2019 — mere days after the letters were first sent — Engels emailed Trinity Prep’s headmaster to request Beute’s personnel file. Mediate was provided a copy of this email to verify and review for content. A screenshot of the email is below, unredacted with the exception of Engels’ email signature with his contact information, and Engels’ and the recipients’ email addresses. Both the cell phone number and email address used for Engels are ones he has had for years.

In the email, Engels acknowledged that as a private educational institution, Trinity Prep was not legally required to disclose any information, but nonetheless urged the school to be “extremely transparent” in order to show Seminole County voters that Beute and Trinity Prep had “nothing to hide.”

“By deciding to run for elected office, Mr. Beute has brought the microscope on himself and Trinity Prep,” wrote Engels, specifically requesting Beute’s personnel file, including records of “any disciplinary action he has faced during his time at Trinity Prep, complaints from parents or teachers,” and “his performance reviews and any student complaints as well.”

Again, at the time Engels sent that email, only the sender of the letters would have been able to inform him of their content and the false accusations they made against Beute.

How the dominoes fell, and fell, and fell…

Sources told Mediaite that it was Greenberg’s obsessive need to destroy Beute’s personal and political reputation that opened the door for all the troubles now swirling around him and his friends, leading to a still-growing number of dominoes falling, one by one, all the way to Gaetz’s doorstep…and perhaps soon others as well.

Greenberg, an independently wealthy man who was interested in cryptocurrency, decided to run for tax collector and allegedly use the resources of the office for that purpose, instead of using his own resources to launch a cryptocurrency business. He is accused of creating a viciously false smear campaign against a primary opponent, Beute, who he most certainly would have beaten if he had just stayed quiet until after the primary.

That alleged smear campaign, supported and promoted by Roger Stone acolyte Engels, attracted enough attention from local press and law enforcement authorities that a sprawling investigation began, warrants were issued, and Greenberg was arrested. Until Greenberg made his easily-traced attacks against Beute, federal and state law enforcement authorities had their suspicions about Greenberg, but do not appear to have had enough evidence to show probable cause to move forward investigating him or to issue the warrants that first gave them access to his computer activities.

Once the door was open, however, Greenberg’s poorly-concealed trail of financial improprieties — again, for allegedly stealing taxpayer funds to purchase items that he could have easily afforded to buy himself — gave investigators ample additional evidentiary paths to follow.

Among the duties of county tax collectors is issuing driver’s licenses, including collecting fees for licenses for new residents, who surrender their old IDs in order to get a Florida driver’s license for their new residential address.

When Greenberg was arrested at his home on June 23, 2020, federal agents found several stolen driver’s licenses in his work vehicle, two fake driver’s licenses in his wallet, and evidence related to creating additional fake licenses at his office. The fake IDs were allegedly created with the photos of Greenberg and some of the young women reported to have been involved in the sex trafficking escapades, but with the names and information from the people who had originally been issued the licenses.

In January 2020, months before Greenberg’s arrest, U.S. Secret Service agents got a tip from an employee of the Seminole County Tax Collector’s Lake Mary office about Greenberg allegedly making fake IDs, including a late night weekend trip to the office in April 2018.

Reportedly accompanying Greenberg on that nighttime escapade: his Congressional buddy, Gaetz.

Text messages the following Monday between the employee and Greenberg mention her seeing him and Gaetz on the office security footage, and Greenberg replying with confirmation that they had been there because he was “showing congressman Gaetz what our operation looked like.” That morning, the employee also discovered multiple driver’s licenses that should have been shredded after being surrendered had instead been removed from the disposal basket and left scattered on a desk.

The Occam’s Razor explanation, as alleged in the indictment against Greenberg, is that Greenberg was showing the congressman how he was able to create fake IDs that could be used to facilitate travel and partying with the young women.

If, hypothetically, someone wanted to travel with a 17-year-old girl for purposes of having sex with her, it would be a lot easier if she had an ID saying that she was a legal adult. And even for the girls who were 18 or 19, it’s a lot easier to get the party going if they have IDs saying they’re 21 and can drink alcohol.

Dr. Jason Pirozzolo, an Orlando hand surgeon, medical marijuana investor, and licensed pilot with his own plane, is friends with Gaetz, Greenberg, and several other Florida Republicans allegedly involved in the sex trafficking schemes. Social media posts have shown the men traveling with Pirozzolo on his plane, and local journalists have dug up several reports of them traveling with young women.

Halsey Beshears, the former Chair of the Florida Department of Business and Professional Regulation, suddenly resigned his position in January of this year, citing personal health troubles. But media reports also have Beshears and several young women traveling on Pirozzolo’s plane to the Bahamas on a September 2018 trip where Gaetz took a commercial flight to join them.

Gaetz changed his personal cell phone number in late December 2020, after federal agents obtained a search warrant and seized his iPhone. Beshears’ resignation came just a few weeks later. Was it really due to medical issues or was Beshears hoping to lay low as investigators swarmed around Greenberg and Gaetz?

It should be noted that so far, Greenberg is the only one who has been charged with any crimes, he has pled not guilty, and despite the growing number of media reports he is entering into a plea bargain with prosecutors, that has yet to be officially confirmed. Gaetz and the long list of his allies and associates who have been accused of being involved have denied any wrongdoing.

The next few weeks will be instrumental in determining how the final chapter of this saga will play out. The next relevant date in the criminal case against Greenberg is May 15, and his defense attorney Fritz Scheller has indicated he believes his client will be able to finalize a plea bargain by then.

“I’m sure Matt Gaetz is not feeling very comfortable today,” Scheller told reporters earlier this month. It seems likely that the congressman is far from alone in that feeling.

UPDATE: Several hours after this article was published, The Washington Post published an article by Matt Zapotosky and Michael Scherer, “How the Justice Department came to investigate Rep. Matt Gaetz,” which independently confirmed much of Mediaite’s reporting on this story, as well as some additional information.