A Fist Full of Dollars — Not a Nickel More or a Dime Less
From C-notes to 1099s — Off-duty policing finally slinks out of the shade and into the sunshine of the Florida Keys.
For years, hiring off-duty law enforcement in Key West and the rest of Monroe County was kind of like falling victim to the Gravity Chronicles under the jewfish at Capt. Tony’s.
Disorienting. Inevitable. Somehow shame-inducing.
Do not ask me how I know.
But enough about me. Back to how do you hire off duty law enforcement for an event?
Used to be with a wink-wink, a nudge-nudge.
A call to “that guy.”
A handshake.
Usually stuffed with $20 bills, sometimes more.
No paper trail.
No IRS.
Just a badge, a horse, a motorcycle, guns, possibly a helicopter or a random drone. Maybe even a paddywagon if you upgrade your subscription
Then there is a smile.
Some would say drug deals were easier.
And all in a community that trusts their law enforcement, hoping for the best, as mandated by state law.
All signs of authority.
Well, now that we know what they are, we’re just negotiating price.
Then, invariably, it comes.
“Cuzzy, bubba… I know a guy.”
That’s how things worked.
On the old days, the sun is setting.
And the times, they are a changing.
“You paid some way for everything that was any good. I paid my way into enough things that I liked, so that I had a good time.
“Either you paid by learning about them, or by experience, or by taking chances, or by money.
“Enjoying living was learning to get your money’s worth. The world was a good place to buy in. It seemed like a fine philosophy.
“In five years, I thought, it will seem just as silly as all the other fine philosophies I’ve had.” — Ernest Hemingway, The Sun Also Rises
Agencies Take the Lead
Following Gov. Ron DeSantis’ call for more accountability, the Monroe County Sheriff’s Office (MCSO), Key West Police Department (KWPD), Florida Highway Patrol (FHP), Florida Fish and Wildlife Conservation Commission (FWC), and Department of Homeland Security (DHS) are bringing their off-duty programs in line with state and federal mandates.
Informal side deals are giving way to formal contracts — and going the way of the proverbial Dodo bird.
Under Florida Statute § 30.2905, sheriffs and police chiefs are authorized to contract deputies or officers for private or public security during off-duty hours.
Employers who hire officers under this statute are responsible for their acts or omissions while on duty, including workers’ compensation coverage.
Officers working extra-duty assignments with FHP, FWC, or DHS retain full law enforcement powers — they can cite, arrest, and detain — but only within the scope of the assignment.
The rules on uniforms, vehicles, and gear are clear.
Serve the benefit of the public trust, or don’t bring it out at all.
How Off-Duty Details Work
All off-duty assignments must now flow through the respective agencies — local, state or federal.
Organizers submit requests — agencies set the rates and issue invoices — and officers are paid as 1099 independent contractors.
According to KWPD public information officer Alyson Crean via email, checks and 1099s are issued by event organizers and then distributed to officers by the lieutenant in charge.
Rates can exceed $75 an hour, depending on rank, event type, and timing.
From 5Ks to Fantasy Fest, the officers still rake it in.
Only now it’s clean money, not a bucci-stained roll of cash that could’ve doubled as chicken-feed.
Off-Duty Work at a Glance
Payment & Tax
Officers paid as 1099 independent contractors.
Checks and 1099s issued by event organizers and distributed by the agency.
Rates can exceed $75/hour depending on rank, event, and timing.
Uniforms & Assets
• Use of department uniforms, vehicles, horses, motorcycles allowed only when part of a plan that serves the public trust.
Private cash arrangements are strictly prohibited.
Liability & Insurance
Organizers must verify workers’ compensation coverage through the agency.
Agreements should be documented in writing to ensure transparency and legal compliance.
Best Practice
Contract all off-duty work through the sheriff or police chief (MCSO, KWPD, DHS, FWC, or FHP).
Avoid informal deals — ensures fairness, accountability, and protection for organizers, officers, and the public.
Lingering Challenges
Some organizers say resistance persists.
“Certain officers still demand cash, wanting to bypass 1099 paperwork while showing up in uniform and with agency vehicles — presenting the authority of the badge without following the formal system. It is almost akin to a shakedown.” — Local event organizer
The practice undercuts transparency, exposes organizers to liability, and reduces the public trust.
As one Conch organizer put it, “Cuzzy, bubba… some folks still want to keep it the way it was.”
But today ain’t like it used to be.
And tomorrow — more than likely — will be different.
There is a reason Conchs earned their namesake moniker.
They have very thick shells and very narrow blue eyes — not exactly an evolutionary recipe for quick adaptation.
Fantasy Fest Leads the Way
Fantasy Fest was founded in 1979 to attract tourists during the off-season.
The 10-day October bash has since grown into a global spectacle — the world’s largest adult homecoming — with everything from body paint to parades.
And now, it’s setting the standard for off-duty employment reform.
Organizers require that all officers — regardless of agency — are contracted, paid, and issued a 1099.
Clear.
Simple.
Accountable.
The system protects the event and ensures officers get the benefits they’re legally entitled to.
It also reduces the grift by rogue officers who’d rather pocket envelopes than file paperwork.
Accountability and Professionalism
Officials from all agencies stress that the updated policies are about fairness and accountability. By requiring off-duty details to flow through official channels, the system protects officers, organizers, and the public — moving the Keys away from handshakes, Cuzzy bubba deals and envelopes — and towards a professional standard.
Who could possibly argue with that? (Wink, wink, nudge, nudge.)
“Enjoying living was learning to get your money’s worth. In Key West, that often meant paying your dues the hard way — through cash, chaos, and questionable judgment.” — Ernest Hemingway
In comparison, LEOs in the Happiest Place on Earth make far less.
Off-Duty Policies and Compensation at Major Florida Attractions
SeaWorld Orlando
Compensation: $27–$44/hour depending on experience and role. Enough to pay for parking and a couple of overpriced churros.
Policy: Must follow park rules; no explicit firearms policy. Translation: don’t spook Shamu. Contact security for guidance.
Walt Disney World Resort
Compensation: Paid for overtime assignments; firearms prohibited. Mickey doesn’t do Glocks.
Policy: Mandatory bag checks and metal detectors; off-duty officers must remove firearms before saying hi to the Mouse.
Universal Orlando Resort
Compensation: Security officers average $19.41/hour in Florida — barely enough to buy a butterbeer.
Policy: No firearms; mandatory metal detection and bag checks. Translation: you’re here to guard Harry Potter merch, not play cop.
Accountability and Professionalism
Officials from all agencies stress that the updated policies are about fairness and accountability.
By requiring off-duty details to flow through official channels, the system protects officers, organizers, and the public — moving the Keys away from handshakes and envelopes toward a professional standard.
A win-win for all involved.
Sometimes, the good old days weren’t all that good.
Especially if your “good old days” involved a bucci-stained roll of cash, a sweaty handshake, and a smile from a thick-shelled, narrow blue-eyed guy with a chronic sinus condition wearing a Key West Conch baseball hat.
Picture it: a Hemingway-esque barroom, neon signs flickering, a half-empty rum bottle, and Cuzzy doing the rooster walk off into the sunset with your wad of crisp $20 bills.
Meanwhile, you’re left in the Gravity Vortex with nothing but a broken coffee mug, a barstool wobbling like a ghost horse, and the faint memory of your dignity trailing behind like the tail of a runaway rooster.
As Hemingway might have said, “Enjoying living was learning to get your money’s worth.”
Hopefully, unlike single-shelled gastropods, the Keys have evolved.