John Sheppard plans to preserve ‘upscale dive bar’

New owner John Sheppard shows off the freshly-repainted facade of the Brass Monkey with arguably Marathon’s most well-known stuffed animal. ALEX RICKERT/Keys Weekly

John Sheppard wants to set a few things straight. No, he’s not closing the Brass Monkey, the bar he purchased on Jan. 18 after 43 years of ownership by community legend Judy Sorenson. No, he didn’t buy the bar just to ship the liquor license somewhere else. And yes, Christmas in July is here to stay.

Originally from New Jersey, Sheppard’s foray into the business came at 10 years old, when he started sweeping the backs of his parents’ bars in Philadelphia and Wildwood, New Jersey. By 13, he said, he was bartending.

“My first trick was I was so small that the register would come over my head, and then I’d make change by putting my hands into the drawer over my head,” he told the Weekly.

Starting with trips to Florida in his late teen years, including visits to the Keys that “get into your soul” he eventually opened or assisted in the opening of six eateries and nightclubs in Pennsylvania, New Jersey and the Sunshine State. He still owns Cattle ’n’ Clover, a “steakhouse with an Irish soul,” in Wildwood and plans to eventually split his time between the two states, but for now, the Monkey is his priority as he lives in Marathon full-time.

“Judy has me set up on third base,” he told the Weekly. “Now, I’m just trying to follow in her footsteps and turn it into a home run. Just trying to update everything and make it cleaner and more welcoming.”

Sheppard’s upgrades as he works towards his vision of an “upscale dive bar” include a new kegerator for ice-cold drafts, repainting the front of the building, repairing broken lights and installing a new register system for greater efficiency in running tabs. He’s got several ideas for promotions and themed parties borrowed from his prior establishments in the works for the coming months.

But apart from indulging his self-described obsessive tendencies as he cleans and reorganizes every space in the building from top to bottom, he said he understands the need to preserve the iconic watering hole’s core essence. 

That includes keeping the staff, from the bartenders to kitchen staff and Freddy Bye’s tunes – and yes, the smash burgers. 

“If you didn’t have Freddy, if you didn’t have Sammy, Dirk, Rodney … you’d be ripping the soul out of Brass Monkey,” he said.

He’s even committed to replacing the bar’s iconic Velvet Elvis in the next few weeks, a custom piece that was one of the only items Sorenson took with her as she closed the sale.

“I think people are starting to calm down now that they see I’m working the door most Thursdays, Fridays and Saturdays,” he added. “This is home to a lot of people, and I understand the nervousness. … But people are confusing me with some billionaire.”

True to her humble nature, Sorenson declined an interview to honor her status as a pillar in the Marathon community for more than four decades. In a heartfelt Facebook post, she shared the news of the Brass Monkey’s sale while thanking the town.

“I am truly blessed to have had such a long run,” she wrote. “I will be forever grateful that because of Brass Monkey, my parents were able to enjoy the last years of their lives traveling and just living. Brass Monkey enabled me to be able to take care of them both when they became sick and needed care, and those are precious moments I will forever cherish and be thankful for.

“Also, how do I even begin to thank this whole town when years ago we were almost shut down. I knew I couldn’t fight big corporate America by myself, but hundreds of people … from literally all over the world stood up for Brass Monkey to fight. And we won! That was something I never saw coming and am once again forever grateful, thankful for and humbled by.

“Please keep going in and show (the staff) some love. … Please show (John) the same love I’ve been blessed to have.

“Thank you for everything. Thank you for the stories and the lifetime of memories that I will carry with me forever … I am truly, truly, forever grateful.”

Alex Rickert made the perfectly natural career progression from dolphin trainer to newspaper editor in 2021 after freelancing for Keys Weekly while working full time at Dolphin Research Center. A resident of Marathon since 2015, he fell in love with the Florida Keys community by helping multiple organizations and friends rebuild in the wake of Hurricane Irma. An avid runner, actor, and spearfisherman, he spends as much of his time outside of work on or under the sea having civil disagreements with sharks.