If you have ever lived or worked in Key West, Fantasy Fest is a rite of passage. It is like the six-week period of Spring Break – I called that the ritual trashing of the city, concentrated into a week-long orgy of craziness, culminating in a final evening of absolute madness – the parade. Come to the Keys, and do as you please. Shit goes on there that would be otherwise proscribed elsewhere in the world – public sex, drunkenness, and recreational drug abuse were de rigueur. Surprisingly enough, there was never any real violence attached to it – sort of weird, but I guess reflective of the mellow vibe of late autumn at the end of the longest dead-end street in America. I got four doses of this potent potion while stationed down there at JIATF-South, and it never failed to amaze.

Fantasy Fest culminates in one grand Mardi Gras-style parade, with a global audience. If you wanted to be a nobody who suddenly became a character in Andy Warhol’s grand prediction, the notion that everyone will get their 15 minutes of fame, and all you had to do to gain this was hand over a personal check for $5 grand to one of the parade float organizers for a ride in the big show. I used to get asked “Does the J-2 have their own float?” Well, officially we didn’t – what we had was the Truman Annex Social Club.

Upon reporting aboard JIATF-South, I found myself sitting on the crater of an almost unimaginable volcano of human brainpower and energy. It was similar to being at FOSIF Rota where I was just a mid-level manager, and part and parcel of that super-heated pyroclastic magma flow that exuded from the Bullring. In Key West, now large and in charge, I had to figure out ways to harness and then unleash their unbridled intellects on the bad guys – we could do anything. Over the next four years, we beat the fucking shit out of those assholes. So it’s no surprise what evolved when we turned our collective attentions to the crafting and execution of a concept for a Fantasy Fest Parade float. The ribald ingenuity and absolute drop-dead cynical, comic and ironic genius of my people was stunning. They would come up with things that were laugh-out-loud funny, and was personified in their interpretation of the various annual Fantasy Fest themes during the float-building process. In retrospect, that we won it all in that craps shoot one year shouldn’t have come as a surprise.

From concept to construction, a lot of thought and skill went into the floats, and not a small amount of “donations.” Led by our principal IC rep, the annual float was started as an idea, and then became reality through his sturdy guiding hand on the tiller. Of course we had to be off-the-wall but relevant – poking fun at society and current events. We also had to have a porta-potty, a keg, and a teetotaler helming our trailered-creation through the byzantine side and main streets of Cayo Hueso.

Anyone in my then mini-empire was invited to participate, as long as they would put some effort or donated money into the float construction. For that small wager, you could either walk alongside and/or ride on the float on the two-mile parade route. I had several of my contractors who flew in just for the event, and who may even be reading this now – you know who you are. It was a tax write-off for you, and a heulluva lot cheaper than paying some local bozo group five grand which what was for us basically a free ride.

The parade itself had several parts – the pre-amble cocktail party in the staging area just outside of the secure perimeter of our compound on Truman Annex, the trek out past the old security gate on Southard Street to Whitehead, a left at the Green Parrot (still one of the greatest bars in the world), a short cruise down to Caroline Street for a right turn over to Duval, and then another right turn at Rick’s across from Sloppy Joe’s – this is where the game really began. There was judgement at the reviewing stand, and then the long march through the raucous crowds down to the foot of Duval, another right back on to Truman Annex, and the post-parade party in the staging area. All told, it took about three hours and then some.

I was invited every year to ride on the float and/or walk in the precession into the bright lights, flinging beads and candy to the rowdy crowds. Since I was the third-ranking Naval Officer at NAS Key West with my picture in every security checkpoint in the base complex (I know because I checked), I didn’t think that was such a great idea, so I deferred. Instead, I would assume a perch on the balcony of a second-story apartment rented by a couple of my guys about a block south and across Duval from Sloppy’s, just down from where the judging of the floats was administered. On the same level of the apartment and across the shared wooden deck of access stairs was Teaser’s – a famous Duval Street strip joint, with its pounding music, rhythmic performers, and colorful clientele. The first time I was there, I asked my guys how hard it was for them to not be over in Teaser’s every night. Their response was pretty classic – “It’s real hard.” For added entertainment, there was also an air brush body-paint booth at street level just below us on the left that at times became an artistic spectacle.

While I wished to remain otherwise incognito, my troops knew where to find me. I would hit the staging area’s pre-parade party, and then walk alongside our float to the Green Parrot, which is where the parade congestion started. Then I would cut through a couple of back alleys over to Duval and my reserved spot on the apartment balcony; more on that at the end.

Once the parade made the right onto Duval off Caroline Street, the craziness really kicked in. The parade started to back up, as the reviewing stand was a couple of blocks further south from us in the direction of Havana. Every float got about a 3-5 minute opportunity to offer a rendition of their schtick for the judges -the central part of that 15-minute Warhol thing. There were the bright lights, a lazy alcoholic haze in the air, and a steady roar of voices and music. It was hypnotic.

During the four years that I was there, our first two float iterations weren’t that much to write a Socotra piece about – we built a float, towed it in the parade, and got drunk – fleet average. Then, it got more interesting. The third year offering was an inspired rip-off of NASA, to include modifying their logo, and featured a penis-shaped rocket dildo mounted on the roof of the tow truck which could be erected on command – our interpretation of the theme was “Rocket to Uranus.” We adopted an LGBTQ mien – a propos for Key West and long before it became fashionable, took a shot at the North Koreans by dressing up one of our more height-challenged team mates in a Kim Jong Il black coolie suit, and had him stationed on the float and waving to the crowd as the personification of that tiny dictator. The unexpected best part of the evening came afterwards, as we had a Brit RAF Nimrod air crew in theater working for us at the time, and they flew up for the party. After the parade was over, they dis-mounted the rocket from the tow truck, and paraded it in and out of Duval Street bars the rest of the night, way into the wee hours of the morning. I don’t think the rocket was ever found. We got third place for originality. That set the stage for next year.

In what had now become a familiar ritual every September, my senior IC rep would come into my office to brief me on the concept for that year’s variation of the Fantasy Fest float theme. Once he told me about his latest inspiration, I intuited that we may have had a winner – we were going to parody our mission, take shots at Fidel Castro, obtain inspiration from the movie Caddy Shack, and riff a little bit on our friends in the Coast Guard. It was ambitious; a little risky – and actually pretty audacious – toujours l’audace.
Cuban Refugees – on a Floating Truck.

The interpretation of the parade theme transformed into “Honest Fidel’s Raft Rentals.” We approached it from front to back in a very holistic manner. Fantasy Fest floats could only have three components – a tow vehicle, a trailer, and the cast of characters. That year, we constructed a cage on the top of the tow truck, and the trailer became a Coast Guard-themed boat, as if it were chasing the tow truck from behind. On the top of the truck, we dressed up one of our beefier and heavily-bearded friends duffed out in original green Cuban combat fatigues featuring an iconic Fidel revolutionary hat – I didn’t ask were that garb came from. Of course, he was smoking a big fat #5 Cohiba. Accompanying him as his nurse while he was portraying Fidel to the crowd was our buxom and darkly exotic protocol officer, Betty Boop, adorned in a white short-skirted nurse’s outfit, completed with a candy-striper-style white hat with its signature red stripe. The kicker was an IV tower which we had borrowed from the local medical clinic – it had a bottle of Cuban rum as the drip to complete the sight picture.

The Coast Guard at that time had recently taken a lot of shit for sinking vintage cars modified by Cuban refugees as their escape vessels by surrounding them with inner tubes and other flotation devices – part of the wet-foot, dry-foot policy. We festooned our tow pick-up truck with inflated inner tubes and old kapok-filled life preservers. People in our entourage who were not part of the design motif and just walking in the parade were required to sport blow-up life rings and rubber duckies. It was a Raft Rental business, after all.

For the trailer, we created a boat out of Styrofoam, and painted it to look like one the Coast Guard would have used for harbor security. It had the signature orange stripe on the bow, and we had the porta-potty and requisite keg of beer on board, of course. The members of the formal marching crew were fitted out with look-alike USCG livery, except we called it the US Conch Guard. We had custom made dark blue tee-shirts and embroidered ball caps – it looked real at first glance, and fooled a lot of drunks. I actually got a call a few days before the parade from my neighbor, the sector commander who had gotten wind of what we were plotting, to ask me to not allow it. I told him first that it was a free country, and I was not in any way in charge of this operation – it was the Truman Annex Social Club. He changed his tune later on, after it was all over.

So, our parade marchers were a collection of faux US Conch Guard members, and people who would wear whatever nautical themed thing they wanted as long as they were carrying a life ring of sorts. We had a volunteer group of women who weren’t shy about wearing bathing suits in front of a crowd, and this is how we won it – Caddy Shack played a key role.

Our act that year was constructed like a high school band parade – you had a banner out front, a drum major, the majorette corps (in our case, the bathing suit crowd), and then the band itself – the float. Every tow-float had to have its own, self-contained music system, but for this one, we had to have two. The first one was just loud Cuban salsa-rhumba music for the marchers to gyrate to, and the second was for the show. On cue, our trusty tow truck driver Mike would switch systems to the deuce – which was Pytor Ilyich Tchaikovsky’s Waltz of the Flowers movement from the Nutcracker as performed in Caddy Shack by a synchronized water ballet – ours was staged on Duval Street. On cue, Mike would hit the music, and our troop would gather in front of the tow truck to perform their version of the waltz. It was a big hit, and the reason we nailed that year’s competition. That’s the good part, but wait, there’s more fun to be had – and a tradition that started long before.

I said up front that my troops knew where I was during the parade, hanging off the balcony of the Duval Street apartment, beer in hand. The parade had a sort of hold short, which was right in front of us. We had been collecting thrown beads, and odd bits of candy and other crap during the evening. We also had a stash of ammo. Our float was normally in the middle of the parade. After about an hour or so, they would make the turn to come up Duval, and pause just below us awaiting their turn in the bright lights on the big stage down the street – it was then that all hell would break loose.

Our float pulled up and stopped below us. “Incoming!” was the first call, and strings of beads began to be hurled back and forth with great gusto. It was fucking awesome to nail one of your troops on the street with a well-tossed throw, only to get two back in return. We would go at it as long as our float was stopped and in range. I still can’t recall any other time that I have laughed my ass off so hard that my sides hurt. It was like that for four years. After my folks had gone through the judges, I would haul ass over to Truman Annex to meet back up with them for the post-parade bacchanal. We would howl with laughter counting coup on the bead fight, and hearing their parade experiences – lots of crazy shit was to be found along the gauntlet down Duval. Waking up that Sunday morning, I checked the Internet and we were world famous on AP for daring to skewer Castro as the face of Fantasy Fest, and winning.

I loved and still cherish my friends down there. We had each other’s backs – worked, played, and partied hard. We survived a direct hit from Hurricane Wilma, rebuilt the command, and even faced with that continued to set interdiction records every year. For me as a leader it was a fantasy come true. It couldn’t get any better – what a place.

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