Captain Tony’s Saloon

428 Greene Street – 305-294-1838 - www.capttonyssaloon.com/

And you thought Sloppy Joe’s was on Duval!

I knew right away this place was a little different. When we walked up to the front, there were a group of drunk coeds standing under the sign on the sidewalk, (fake breasts threatening to slip out of seriously strained bikini tops), facing the street and trying to chuck pennies up over their heads into the mouth of the big fish on top of the sign. I don’t know the history behind this, but I can only assume it’s a good luck thing. I certainly felt as if my luck was changing!

I’d been here once before for a couple of beers, but had to come back to grab some photos for this post (oh darn). Captain Tony’s is a place like no other, the ceilings and walls (every single available scrap of space) are covered with thousands upon thousands of business cards, panties, license plates, old junk, and bras.. bras, bras, bras.. everywhere you look bras. It’s literally impossible to make out what it all is, there’s so much of it.

Then there’s the tree. A huge old Oak, growing right up through the middle of the floor and out the roof! It’s dark, dingy, and utterly key west through and through.

A rich and infamous history

This is the original location of Sloppy Joe’s Bar, the actual place Hemingway hung out in in the early 1930′s. Sloppy Joe’s was owned by Joe “Josie” Russell. Hemingway immortalized his friendship with Joe in his book To have and have not by using him as the basis for Freddy, the captain of the Queen Conch, and owner of Freddy’s bar.

The building had been many things before Joe Russell bought it in 1933. It was a telegraph station in 1898, after that it was a cigar factory, a bordello, several speakeasies, the county morgue, and an icehouse.

Joe Russell moved his bar out of the building in the middle of the night over a dispute with the landlord, and the building housed a gay bar through the 40′s and early 50′s

Captain Tony bought the bar in 1958 after hitchhiking to Key West from New Jersey on the back of a milk truck.  He’d left NJ to avoid being chased down by mob bookies to whom he’d managed to annoy quite seriously.

During his fantastic life of 92 years, Captain Tony fathered thirteen children by three wives, had been a Charter Boat Captain, a Gun Runner for Cuban mercenaries during the Bay of Pigs, and was elected mayor of Key West in 1989, his campaign slogan being; “All you need in this life is a tremendous sex drive and a great ego. Brains don’t mean shit.”

His goal while mayor was to limit growth and to have Key West maintain its reputation as a refuge for eccentrics and renegades. He was quoted by the Chicago Tribune as saying “Key West is an insane asylum. We’re just too lazy to put up walls or fences, I want to retain that mystique.”

Captain Tony passed away in 2008; he’d sold the business almost 20 years earlier, but was still a constant fixture at the bar, and he spent his time signing autographs and visiting with the patrons.

Now HERE was a guy I would have absolutely loved to meet, I’m really sorry I got here a year too late to make that happen. Captain Tony, you sound like my kinda folk!

The Lady in the Blue Dress

I’m still digging for this story, and when I get it figured out, I’ll post it up in the ghosts of Key West section, but for now here’s a quick rundown. Apparently during the time when the building was used as a morgue, that big old tree that now grows through the roof, was the town hanging tree.

A woman who had killed her husband and son was hung from that tree, along with a few other miscreants over the years. When a huge storm hit Key West and demolished the morgue, they found bodies all over the place in the aftermath.

I’ve heard a couple of versions of this, one is that they cremated the bodies and filled glass bottles with the ashes, which they then embedded into the concrete foundations of the rebuilt structure. Another version states the bottles were filled with holy water to keep the restless spirits at bay. It’s hard to find reputable stuff about this online, but sure enough, the bottles are there in the foundation. I’ll keep digging.

The ladies restroom is supposed to be haunted by the ghost of the lady in the blue dress. Christina didn’t see anything in there during her visit, so the Jury is still out!

A good place to hang out

I like Captain Tony’s, it rates right up there with Schooner Wharf for down and dirty local character. There’s usually some sort of live music, and always a lot of interesting folk. It’s a block off Duval so it’s not totally overrun by sweaty sunburnt tourists. And you can hardly pass up the opportunity to run into a ghost in the ladies room!

Check it out!