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10 craziest Florida criminals of all time

By / 04.06.14

craziest florida criminals

What’s going on in the Sunshine State? I don’t know, but it certainly seems to drive people insane. It seems like every week there’s a news report from Florida that’s totally bananas. Today we’ll spotlight the ten most mentally deranged crooks to ever get booked in Florida.

10. Naked Pooping Masturbating Burglar

It takes a certain amount of chutzpah to break into a house naked, but Fort Myers burglar Gregory Matthew Bruni has plenty to spare. After he forced his way into a home in early 2013, Bruni wrestled a 72 inch flat screen TV off of a wall, breaking it in the process, before the lady of the house pulled a revolver and fired three warning shots. With his life near an end, Bruni did the only sensible thing: he dropped to his knees and started masturbating. He then pooped in a hallway and when cops arrived they found him sucking up spilled water from a wet/dry vacuum into his mouth. All part of his cunning plan, I’m sure.

9. Donkey-Humping Constitution Challenger

It’s not just the crime that makes a Florida criminal crazy – sometimes it’s the court case too. Carlos Romero was picked up in 2012 for having sex with a miniature donkey named Doodle. The state offered him a plea deal involving a cash fine and psychological evaluation, but he decided to take this one all the way to the top. He actually found a lawyer willing to challenge the animal sex laws on a constitutional basis, claiming that bestiality laws were an infringement of his right to privacy and personal liberty. He eventually pled guilty and then was arrested again for stealing train batteries. Hopefully he wasn’t having sex with those too.

8. Machete-Wielding Toilet Vandal

In April of 2013, Luis Guillermo Alicea was awaiting trial in Jacksonville for a bevy of crimes when he decided that he could do better. So he grabbed a machete and set off down Heidi Road on foot yelling “Kill me, I want to die.” The knife-waving maniac tried to break into two houses before getting into a third, where he embarked on an orgy of destruction that climaxed with him ripping a toilet out of a second floor bathroom with his bare hands. He then jumped out of a second story window and was taken into custody by the cops, who reported that he was foaming at the mouth.

7. Two-Day Senior Citizen Exorcist

David Edward Benes

Pasco County Sherrif



Religion is a big part of life in Florida, so it’s unsurprising that some crimes get committed for Jesus. When David Edward Benes got into a fight with his eighty year old girlfriend (Benes was a relatively spry 54 at the time), things escalated in a very Florida way – he decided she was possessed by Satan. The demented boyfriend trapped his octogenarian lover in their house for two days as he tried to exorcise the evil spirits from her, only for the cops to come and haul him off.

6. Naked Sword Dueling Lawyer

The myriad criminals of Florida probably need a pretty good lawyer. Terry Lee Locy… is not that lawyer. The Broward County attorney was arrested in 2011 after a drunken argument with his girlfriend went wildly out of control. The lady wounded the soused lawyer by throwing a hook at his head, and in response he took a shower, walked back in the room in the nude, handed his lady a samurai sword and challenged her to a duel to the death. Like a coward, she called 911 and had them come pick up her naked lawyer samurai lover.

5. Old-School Corpse Lover

Crazy crime in Florida isn’t a recent invention – people have been doing all kinds of weird stuff there since before it was a state. On the outside, Carl Tanzler was a pillar of his community – a radiologic technician at Key West’s United States Marine Hospital who was devoted to his job. When a Cuban-American girl named Elena Milagro de Hoyos checked in for tuberculosis treatment, he fell instantly in love and attempted to win her affections with extravagant gifts. After she died in 1931, Tanzler broke into her mausoleum and stole her body. He took it home and kept the decaying corpse in his bed for seven years before being discovered and arrested.

4. Bush Doctrine Double Murderer

William Woodward

Titusville Sheriff



One common thread among Florida criminals – especially the insane ones – is that they come up with some pretty amazing motives for their dirty deeds. When William T. Woodward snuck up on three of his neighbors during a Labor Day barbecue and shot them all dead, his defense was invoking the “Bush Doctrine” that was used to justify the war in Iraq. Woodward claimed that the men had called him names and threatened to “get him,” and he thought that was good enough reason to pre-emptively murder them, just like W. would do.

3. Moronic MacGyver Squirrel Killer

Living with varmints is just part of getting by in Florida, but when a Gainesville man decided to employ lethal force against a delicious squirrel, things got a little crazy. William Daniel Lloyd was trying to shoot a squirrel for dinner and rigged up an idiotic improvised weapon by taping a .22 cartridge to the barrel of a BB gun and tried to use that to cap the rodent. Of course, when he fired it the bullet fragmented and drove shrapnel into his own leg. He was rushed to the hospital and cited for discharging a firearm in public.

2. Naked Masturbating Driver With A Toy Gun In His Butt

Florida has more arrests for public masturbation every year than the rest of the continental United States combined. Think about that for a minute. A particularly demented case came in 2012 when a truck driver on I-95 outside of Fort Pierce called in a report of a man in a Jeep Cherokee cranking his hog while he was driving. When cops caught up to him, the man – identified as Robert Leo Casey – was still trying to put his clothes back on. The police pulled him out of his car and discovered that he also had a toy pistol half-crammed up his butthole with a cord from the handgrip tied around his ballsack.

1. Chihuahua Fingerblaster

Tomas Bautista

Broward County Sheriff



Here’s another grotesque animal story that’ll have you wondering just how horny Florida is. Tomas Bautista is an Oakland County man who will readily admit that he “gets crazy” when he drinks. One February night when he came home from a particularly wild bender, he saw his elderly roommate’s Chihuahua dog in the yard and something… happened. Bautista dropped his pants, whipped out his ding-dong and stuck his finger in the dog’s vagina. It yelped and ran away and the sick perp passed out on the lawn with his pants around his ankles.



Dumb criminal image by Shutterstock
(Previously published on October 10, 2013.)


TAGSAnimalsArbitrary RankingsbeastialityCrazyCrimecriminalsdonkeydumb criminalsdumbest Florida criminalsfeaturedFloridaFlorida CrimeFlorida manfunny Florida crimesListsMasturbationnaked manpoopweird criminalsWeird Floridaworlds dumbest criminalsworst Florida criminalsWTFwtf florida
About K. Thor Jensen... K. Thor Jensen is an award-winning writer and graphic novelist who lives on a tiny island in the middle of nowhere. His website is Shortandhappy.com. He fought six Draculas and won.

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