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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


Black befriended Alfred Hair, one of the first Highwaymen and the leader of the group, who recognized Black’s potential as a salesman for the group. Hair drew Black into the business, and he quickly became a prolific salesman.

“I would sell to anybody, from motels to doctors and lawyers,” Black says. “Whoever I came across, I would try to get them to buy. Nobody was as good as me at selling. I could sell ice in Alaska.”

Black took the Highwaymen’s business to new heights. He expanded their market, selling paintings throughout Florida and beyond, though the law would sometimes get in the way of business.

“I traveled up the Atlantic seaboard, from Key West and all the way up to Portland, Maine,” he recalls. “Sometimes I would get thrown in jail for a few days, since a license is required in each state to sell. It was hard times.”

Black’s painting career got started more as a necessity than an artistic urge. As he traveled, the paintings got bumped around and sometimes they needed a bit of touch-up.

“When I would be traveling with all the paintings in the back of my Cadillac, they would get smudged,” he says. “So, I would have to fill it in – a little of the sky, a little of the tree.”

When he would return to the Highwaymen’s home base in Fort Pierce, Black learned techniques from the other artists, too. The group, known for mass-producing many of its paintings, would often have backyard barbecues where the artists would work on the next batch of landscapes together. Sometimes they even painted in assembly-line order: painters would specialize in creating parts of a painting – one might paint water, another would do clouds, yet another would do trees. At times, the group could complete 35 to 40 paintings in one evening.

Black and the Highwaymen were economic in their artistic approach, carefully minimizing the number of brush strokes and amount of paint needed to create a piece. To keep expenses in check, they would use cheap materials, like house paint and Upson boards used by roofers, whenever they could. They would build frames out of door trim.

The paintings didn’t sell for much – the prices ranged from $15 to $25 per piece – but with Black’s help, the artists could sometimes bring in as much as $5,000 a week in sales.

By 1970, Black and the Highwaymen had earned a pretty good living selling paintings. Black says he was driving a nice car (at one point, he says, he owned three Cadillacs) and in the spring of that year he married and started a family.

In the summer of 1970, he and Alfred Hair had planned a meeting to discuss a trip to sell some new paintings. The night they were supposed to meet, though, Hair was shot and killed in a brawl at a Fort Pierce bar called Eddie’s Drive-In.

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