Florida education chairman’s dirty dredging case represents a failure to communicate
Tom Grady. Image via the Florida House

Tom Grady
Tom Grady didn’t realize hurting the Keys’ environment hurts everyone

One of the dumbest things I ever did was skip the chance to learn Spanish. While most of my high school classmates were busy habla-ing their Espanol — which turns out to be pretty handy here in Florida — I was bungling my way through German like a dummkopf.

I took German because I was a teenage boy and the German teacher was a former Miss South Carolina. Turns out that’s a really bad reason to sign up for a language class. I don’t remember much of what we studied, other than how to count to 23 (“drei und zwanzig”) and sing the first verse of “Silent Night” (aka “Stille Nacht”).

But, as a result, I do know how to pronounce schadenfreude. I know the definition, too. It doesn’t mean “giving your friend some shade on a sunny day.” Instead, it’s a German psychological term for when you feel a tremendous surge of glee at hearing about some misfortune befalling a person who reeeeeeally deserves it.

Someone like Tom Grady.

No, not Tom Brady, the Buccaneers’ star quarterback. I mean Tom Grady, a Florida political insider who’s spent years being one letter away from a Super Bowl ring.

Grady is chairman of the Florida Board of Education. He was appointed to the board, despite having little prior experience in the educational field, by former Gov. Rick Scott, who also happens to be one of Grady’s neighbors in Naples. He was subsequently reappointed by Gov. Ron DeSantis, who may be sorry he did that now.

Grady, a wealthy securities lawyer, has been a faithful foot soldier in Gov. DeSantis’ war on locally elected school boards. He helped lead the charge against those scofflaw school officials who required students to wear masks to stop the spread of coronavirus in the schools, threatening to yank their funding or have them removed from office. How dare they put the health of the students ahead of the governor’s ideologically driven wishes!

(If the Governor were as vehement about stopping the virus as he is about stopping locally elected officials taking actions he doesn’t like, Florida would have a much lower death rate. But I digress.)

Chairman Grady made the news for a different reason last week, and you could pick up more than a whiff of schadenfreude in the coverage of his case in, say, the Palm Beach Post, which referred to him as “your basic fox-in-the-henhouse guy.”

Grady was charged by the feds with illegal dredging at a property he owned in the Keys. He turned himself in on Oct. 8 and was released on $50,000 bond, according to the Miami Herald.

It’s easy to understand why some people might get a fit of the giggles about Grady being charged with a crime. It’s not just that he’s the one who’s been telling local school boards things like, “Every school board member and every school superintendent has a duty to comply with the law, whether they agree with it or not.”

It’s that Grady falls into a category of people I call “Earwigs,” which is short for “Environmentally-Destructive Rich White Insensitive Galoots.” (Yes, I know it’s not a pure acronym. I’m enough of a galoot that I don’t care.)

Grady’s career in public service is littered with examples of him doing clueless but expensive things, which is what you’d expect from an Earwig.

As the Tampa Bay Times noted when he was appointed to the education board, “During his brief tenure in the House, Grady was notable for billing taxpayers for flying on private planes owned by a campaign donor. He also pushed for tax breaks for some of Florida’s richest residents. As interim president of Citizens Property Insurance, he also racked up large hotel and travel expenses on the state’s dime. During his short time there, he also created a new job for his former legislative aide.”

My favorite detail from the Times’ reporting about his time running the Office of Financial Regulation (yes, that’s a real agency name) is that he and his wife went to a Tallahassee store and bought more than $11,000 in furniture for his office, including “a $2,658 console, a $2,660 bookcase, a $2,482 black leather sofa, a $925 mirror, and a $563 floor lamp.” Yes, when you’re regulating financial companies, you need the finest furniture for your office! Especially a mirror!

But when he submitted the entire furniture bill to the state for reimbursement, state officials said they could not legally pay him any more than $3,864. Fine, he said, he’d just take all that furniture with him when he left.

A savvy Florida politician would have looked at Grady’s track record and said, “Nope, not gonna reappoint that guy.” Alas, our current Governor is really bad at appointing people, and now here we are.

There’s been the expected tut-tutting over DeSantis not suspending the accused from his office, the way he has some local officials accused of a crime. I suspect he’s following the rule that everyone is presumed innocent until proven guilty, as long as they are members of the DeSantis administration.

But what I want to talk about here is not how deserving Grady is of a comeuppance. I want to talk about what he’s accused of doing — illegal dredging in the Keys.

No permit for you!

The Florida Keys — long known as a haven for wreckers, smugglers, and pirates — has always had a tolerant, if not bemused, attitude when it comes to crime. One bail bondsman there carries business cards that say, “Come on vacation, leave on probation,” which I think would make a nifty state motto.

The scene of this particular crime was Islamorada, which consists of four islands: Plantation Key, Windley Key, Upper Matecumbe, and Lower Matecumbe Key. Canals snake through the Keys, and Islamorada is no exception. There are 64 canals, totaling approximately 24 miles — longer than the total length of the four-island chain.

According to the charging document filed by the U.S. Attorney’s Office, Grady “did knowingly excavate and cause to be excavated” a boat channel without authorization from the U.S. Army Corps of Engineers, the agency that since 1899 has issued federal permits for such work. Grady allegedly did his dirty work in April 2017 at 87429 Old Highway on Windley Key in Islamorada.

Monroe County property records show that address is a million-dollar waterfront home that Grady appears to have bought for $1.4 million in 2013. He renovated it, then sold it to a Rhode Island man five years later for $4.1 million, making a tidy profit indeed.

The renovation process had its bumps. The town’s code enforcement officials slapped a stop-work order on the project at one point. They did that because of what they judged to be an illegal excavation. But that’s not what has the feds ready to haul Grady into court. No, the problem here is the boat channel giving the property access to the Atlantic Ocean.

Federal prosecutors declined to answer any questions about the case, as did Grady’s attorney, David Markus. Markus did send me a statement that his client “obtained numerous approvals for this project from the local, state, and federal government. Unfortunately, the federal government’s position is that any existing federal permits were insufficient.”

But when I talked to folks in and around Islamorada, they told me Grady couldn’t have gotten a permit that allowed dredging a boat channel.

Nobody can.

“In my lifetime, I have never known of a dredging permit being issued in Islamorada,” former Mayor Chris Sante told me, making it sound like there’s a cousin of the Soup Nazi telling everyone, “No permit for you!”

There are no dredging permits because the whole area is part of the Florida Keys National Marine Sanctuary. A law passed by Congress in 1990 set up the sanctuary to protect the marine equivalent of the Amazonian rain forest, explained attorney Julie Dick, who’s represented several Keys environmental groups.

“You don’t want people dredging coral reefs or sea grass beds,” Dick told me. “You could impact marine mammals, or a nursery or a place where fish congregate. Dredging has environmental consequences on the ecosystems that drive the economy of the Keys.”

Only occasionally do the feds issue permits for “maintenance dredging” — in other words, cleaning out debris and silt from old canals, particularly after a hurricane.

The Corps didn’t want to comment about anything even remotely related to the Grady case, but the Keys sanctuary staff told me they get an average of 25 requests for maintenance dredging permits a year for the whole Keys region.

That’s the kind of permit that Grady got from the Army Corps in 2016. He was approved “to dredge 1,066 cubic yards of submerged bottom … within the existing dredge channel and boat basin.”

That’s not the kind of dredging work he did, according to records I reviewed.

Water, water everywhere, but how to get there?

If you’ve ever visited the Florida Keys, you may have noticed there’s lots of water all around you. It’s the main thing attracting people to the area — unless you’ve put on an outlandish costume and you’re headed for Fantasy Fest.

But getting access to all that water is tricky because of that ban on dredging. Water access, say the Keys folks I talked to, can make the difference of a couple of million dollars on the value of a parcel.

Next door to Grady’s property is a home with the perfect access to deep water — its own boat channel, straight as an I, dug out decades before we knew what damage it might do. What Grady wanted, it appears, was to dig his own channel to connect to that one, making a Y out of an I.

An aerial photo included in the town’s paperwork for Grady’s property shows no channel connecting Grady’s property with the boat channel. In fact, according to one former town official I interviewed, a city employee donned snorkel gear (not for Fantasy Fest, either) to check it out. He swam through that area to document that there was no channel, just untouched hard bottom. (Come to think of it, the Corps should have done something similar before rubber-stamping Grady’s permit request.)

There sure is a channel there now. You can see it on Google Maps. I haven’t got the greatest eyesight in the world, but I found it as easy to spot as it would be for Tom Brady (the quarterback) to spot an open receiver in the end zone.

Wait a sec, I thought to myself. Maybe that channel isn’t Grady’s fault. Maybe it’s the fault of the contractors he hired.

But then I saw an email that Grady sent to an Islamorada official in which he wrote, “As you know, I have personally been involved in the permitting process because it is important to me to comply with the letter of the law, despite the fact that it is frequently gray and appears subject to much discretion.”

Gee, sort of like the whole masks-for-kids thing, eh?

Grady’s trial is slated to begin on Nov. 22 in Key West. I can’t predict how it will turn out because Florida juries do wacky stuff sometimes. I once saw a bigamy trial in which the defendant swore he’d just forgotten he was married. The jury bought it.

But if I were the prosecutor, I would put those two pictures up in front of the jury box and turn to Grady and say, “Explain this.” If I were his defense attorney, I’d be pushing the “who you gonna believe, me or your lying eyes?” strategy.

If he’s convicted of dirty digging, Grady could face criminal penalties that include up to a year behind bars. But I have a different, somewhat unconventional proposal. To paraphrase the warden in “Cool Hand Luke,” I think what we have here is a failure to communicate.

Clearly, Grady doesn’t understand that this isn’t some meaningless rules infraction. What he’s done damages everyone in the Keys. After all, if you hurt the environment there, then you’re hurting the economy.

I propose the defendant be put to work creating an English-to-Earwig dictionary for the benefit of other wealthy galoots like him.

This English-to-Earwig dictionary, written out while Grady sits on his fancy office furniture, would spell out in both languages exactly why what he did was wrong. It would also explain what’s wrong with other acts of environmental destruction, such as dumping pollution into the waterways or digging a trench in seagrass with your propeller or slicing up a manatee with your speeding boat.

I think this language-related solution would be one that Grady himself would welcome. After all, it’s rooted in a desire to improve someone’s education — his.


Craig Pittman reporting for Florida Phoenix.

Florida Phoenix is part of States Newsroom, a network of news bureaus supported by grants and a coalition of donors as a 501c(3) public charity. Florida Phoenix maintains editorial independence. Contact Editor Diane Rado for questions: [email protected]. Follow Florida Phoenix on Facebook and Twitter.

Craig Pittman

Craig Pittman is a native Floridian and environmental correspondent for Florida Phoenix. During his three decades at the Tampa Bay Times, he won numerous state and national awards for his environmental reporting. He is the author of the New York Times bestseller "Oh, Florida! How America's Weirdest State Influences the Rest of the Country," which won a gold medal from the Florida Book Awards. His fifth book, published in 2020, is "Cat Tale: The Wild, Weird Battle to Save the Florida Panther." The Florida Heritage Book Festival recently named him a Florida Literary Legend. Craig is co-host of the "Welcome to Florida" podcast. He lives in St. Petersburg with his wife and children.


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