Matthew Sheehan: The man, the myth, the laugh

Bartender Matt Sheehan gives two thumbs up. COURTESY PHOTO

Bartender Matt Sheehan gives two thumbs up. COURTESY PHOTO

Let’s forget the formalities and call Matthew Sheehan “Matt” from the get go, because he really is your quintessential friendly neighborhood bartender. Meet Matt. Matt is always happy. Matt is always smiling. He rarely ever looks angry or upset and he has one of the most contagious, engaging and lovable laughs on the island. When he lets one loose it sounds like he never let go of his childhood innocence. He’ll laugh longer and louder than anyone else, which in turn, makes everyone laugh twice at the same thing and next thing you know you’ve been laughing for five minutes straight. Because of this, it is almost impossible to sit at Matt’s bar and not have a jolly good time, literally.

“Matt is one of the nicest bartenders I’ve ever met,” regular Bradley Garrison says, “He’s always smiling and laughing. He’s also a great bartender for his love of fake wrestling.”

“Fake wrestling is more real than most things. It’s scripted, not fake,” Matt jokes in response, “And sometimes it’s an escape from the monotony of all other sports I’m always surrounded by.”

Matt works at Jack Flats, 509 Duval St., five days a week, Thursday through Monday, from 5 p.m. until close, which can be as late as 2 a.m. Around the large dining room and behind the long stretch of bar that takes up almost an entire length of wall, are 19 big-screen TVs that broadcast everything from soccer to hockey to basketball and, of course “real, not fake, scripted” wrestling. And let’s not forget football. The place hosts a yearly Super Bowl party with a VIP list of well knowns within 100 miles.

The food here is American comfort. Think salads and sandwiches, pot roast and meatloaf. Matt’s favorite is the blackened mahi sliders served with homemade key lime mayo.

There is no specialty drink menu, but they pour a lot of beers and shots and can make whatever you want.

The atmosphere is almost always buzzing if there is a game on. It’s not fancy by any means. It is just the right amount of casual to be easygoing, but doesn’t even come close to being a hole in the wall. This is a place where you can take your whole family, meet for a very first date or just have a quiet night out with friends. Everyone is welcome.

“It’s a good mix of locals and tourists,” Matt explains. “It’s basically people who like sports and good food. It can be wild and crazy at times or a perfect place for those looking to escape.”

Jack Flats is somewhat of a rarity in Key West when it comes to staffing. Whereas a lot of other places experience a high turnover, Jack Flats is well known for its long-term bartenders who provide a sense of normalcy for returning patrons. Matt has been a familiar face since 2003, after he first moved to Key West following an eventful summer the year before when the RV that he and three of his best buddies drove down from his hometown in New Hampshire broke down. Matt and his friends got a little taste of Fantasy Fest and decided they would make a pact to come back for “more.” The next year that “more” turned into 14 years in Key West and now Matt has a wife, a daughter named Maddie, and two dogs named Penny and Foxie.

Although Matt has been at Jack Flats for almost all of his bartending career, it isn’t the place that introduced him to the service industry. He recalls helping at his uncle’s restaurant when he was just 10 years old and how his first real job on the island was actually at Shorty’s Market in the 200 block of Duval across the street from Rick’s. His first bartending job was at Caroline’s Café at 310 Duval, which is one of Jack Flats’ sister restaurants, along with Fogarty’s, Red Fish, Blue Fish and the Waterfront Brewery.

“It just doesn’t feel like work to me. It’s fun,” he says of his devotion to the industry.

Matt’s laugh might be contagious, but he genuinely wants people to leave smiling and thinking about the next time they’ll come back to the bar. I know this, because he told me so. He genuinely loves his job. From the day he started with the company, he felt as though it trusted and respected him and he proved it wasn’t wrong. His commitment to the job is something worth seeing for yourself.

Yet, as much as he loves bartending, it is only second to his love of spending time with his family. His favorite things to do are to go paddle-boarding with Maddie sitting at the front of the board and relaxing, which is exactly how he describes his bartending style. Just “relaxed.”

“I used to want to be an astronaut,” Matt says when he mistakes my question, “What do you think people should know about you?” for “What did you want to be when you grew up.?”

“I used to want to send people to the moon. Now I send people to space in a different way,” he laughs.

That is Matt.

The man, the myth, the laugh. ¦

2 responses to “BARTENDER OF THE WEEK”

  1. Cori says:

    Great guy!
    A former neighbor

  2. Patricija Hambrook says:

    The nicest guy in the world. ♡☆♡☆♡☆♡☆♡☆♡

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