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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

Without their leader and visionary, the Highwaymen lost focus. According to The Highwaymen: Florida’s African-American Landscape Painters, written by Gary Monroe, the painters continued to work through the 1970s and ’80s, but the organization disintegrated. “There was nothing to shoot for after Alfred died,” Monroe quotes one of the Highwaymen, Hezekiah Baker, as saying.

Demand for the paintings dropped as well. Fewer people were traveling Florida’s meandering state roads, where the Highwaymen often hawked their wares, opting instead to take newer highways to their vacation destinations. Laws forbidding solicitation in public places made it harder to find places to peddle. By the 1980s, the highly stylized paintings were beginning to look dated and generic to people.

As the Highwaymen’s tight-knit group was falling apart, so was Black’s life. He got involved in drugs, and by the mid-1990s, he wound up in jail on a string of drug charges. In 1995, the St. Petersburg Times (now called the Tampa Bay Times) profiled a Kissimmee art collector who had rediscovered the Highwaymen and was trying to reach out to Black, who had been in and out of jail and was living in a dilapidated boarding house in Fort Pierce. He had stopped painting, according to the story, because he had no money for paint or supplies. Two years after that story was published, he landed in jail again, this time for allegedly conning money of an elderly widow who had tried to help the struggling artist. Prosecutors said Black used the money he got from the old lady to buy cocaine, and he was sentenced to 12 years, which he served at the Central Florida Reception Center.

Part of the jail specializes in housing inmates with special medical needs. Black was HIV positive. One of the guards at the jail (who is unnamed in this story, for his security) often allowed Black to paint in his office near the jail’s laundry room. During a recent tour of the facility, the guard’s face lit up as he showed off the work Black did during his imprisonment. Most of the landscapes were painted right on the cold, concrete walls of the jail, with permission from the warden.

During his time at Reception Center, Black developed a new trademark for his paintings. He had always liked to include a trio of birds, flying in formation, in his works. He said they represented the Holy Trinity. In jail, he decided to add a fourth bird.

“The fourth was out of formation,” Black says, “symbolizing my fall from grace.”

The prison murals create an ambivalent scene in the halls of the Reception Center. Everglades grasses and flowering royal poincianas are juxtaposed with fire extinguishers and “no smoking” signs. According to Monroe, who also authored a book about Black’s prison works called The Highwaymen Murals: Al Black’s Concrete Dreams, the population at the jail knows that some of the artist’s best works are embedded in that place.

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