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COVER STORY

Artist on the outside

How the work of one of the famed Florida Highwaymen ended up behind bars in an Orlando jail

Photo: Barry Kirsch, License: N/A

Barry Kirsch


“Both prisoners and staff, by and large, realize the worth of the murals,” Monroe says. “Images of idyllic Florida transform the institution, and prisoners speak reverentially under their influence.”

When asked whether he thinks the current administration at the jail or at the Department of Corrections in Tallahassee realizes the historic and cultural significance of the paintings on the jailhouse walls, Monroe is philosophical.

“Nothing with form is permanent, and the murals are where they belong,” he says. “They’ll age, though vandalism hasn’t been a problem. Maybe they will be whitewashed over at the call of a warden, or maybe Tallahassee will have the buildings razed and replaced with new buildings. The paintings will have served their purpose.”

While Black was doing his time, the paintings of the Highwaymen boomed in popularity. Paintings that had been selling for just a few bucks at a thrift shop in the late 1980s and early 1990s were rediscovered by collectors and were suddenly fetching hundreds and even thousands of dollars. In 2004, all 26 of the Highwaymen were inducted into the Florida Artists Hall of Fame.

Black was released from the Central Florida Reception Center in 2006, in time to cash in on the renewed popularity of the long-forgotten artistic movement. By spring of 2007, he was back at it: painting and selling, wheeling and dealing in art.

“As soon as I got out, I moved back to Fort Pierce,” he says. “I contacted all the Highwaymen and started doing business again.”

These days, he’s making a living as an artist, and he can often be found traveling the coast again, from Cocoa to Orlando to Fort Pierce to Winter Park. He’s a regular at art festivals and fairs, selling his landscapes for prices ranging from $350 to $1,500, and for those who can’t afford those prices, he also sells T-shirts, buttons and postcards adorned with his works on his website.

He’s a giant of a man who has to duck his head as he enters his vendor tent at a festival in Hannibal Square in Winter Park. His Southern drawl, booming voice and charming demeanor always get the attention of passersby. When they stop to admire his work, he smiles widely and hands them his card – just like he used to do back in the day when he was driving his big old Cadillac with a trunk full of paintings up and down the eastern seaboard.

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