March 10, 2021

Over the years, we’ve written a fair number of stories about frustrated taxpayers choosing to cut their bill the old-fashioned way: by cheating. In today’s America, which seems more divided than at any time since the Civil War, tax cheats truly cut across all lines — political, racial, religious, and socioeconomic. (Last year, the Justice Department indicted two Forbes-certified billionaires for tax fraud). Some of their schemes are so clever you really wonder why they didn’t just go legit.

We’ve also written about tax professionals breaking the rules for clients. You probably don’t think of tax nerds as a bunch of bad hombres. But accountants have stolen more money with their pens than bank robbers like Willie Sutton or Bonnie and Clyde ever “liberated” with a gun. Remember Enron? They never would have conned so many people for so long without the Arthur Andersen seal of approval. (Oh, and when we say “bad hombres,” we don’t mean to exclude women who cheat for their clients. None of them seem happy with stealing 79 cents for every dollar a man steals.)

So, taxpayers cheat. Tax pros cheat. I know, film at 11. But it’s rare that we get to take aim at tax collectors doing it. Which brings us to this week’s story, featuring “Florida Man” Joel Greenberg.

In 2016, Greenberg won the race for tax collector in Seminole County, just outside of Orlando. The office came with a $70,000 salary and 100 employees spread over six offices. The job included a full boat of responsibility over property taxes, local business and tourist development taxes, hunting and fishing licenses, drivers licenses and license plates, and sales taxes on cars, boats, and mobile homes.

But somehow Greenberg found time to test new ways of collecting revenue, like encouraging employees to pack heat and buying equipment to take payment with Bitcoin. Auditors eventually found he “wasted more than a million dollars on vendor contracts, hired unnecessary staff for around $1.65 million and had questionable credit card charges of $384,000, including for weapons, ammo, body armor and a drone.” (A drone? Really?!?) And he saddled the county with $1.4 million in legal costs, including $215,000 to settle harassment charges from seven subordinates.

Then things got weird. And creepy. Last June, federal prosecutors indicted Greenberg on charges of stalking. Apparently, he set up fake social media accounts to accuse a political opponent, who works at a school, of sexual misconduct with a student. Two months later, another grand jury filed a superseding indictment (i.e., piled on even more charges) for sex trafficking a child (projection much?) and illegally accessing Florida’s drivers license database for information on “sugar babies” he was paying for sex.

Greenberg had been free on bail since his arrest, with the usual stipulations that he stay in the Middle District of Florida and not leave his house between 8 p.m. and 6 a.m. But it seems his arrest was an invitation to humility that he declined. Last Sunday, he broke curfew to chase down his wife at her mother’s condominium in Jupiter, near Palm Beach. She called police, and now Greenberg is cooling his heels in jail.

Greenberg probably didn’t set out to become the poster child for misusing his office, but here we are. The good news is, Seminole County has a new tax collector dedicated to restoring the office’s integrity. And you have a powerful resource in the form of us to help you pay less without risking an electronic ankle monitor!

Don’t hestitate to contact us.

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