Art, Race And Murder: Meet Florida's 'Highwaymen'

The story of The Highwaymen is one of biracial friendships and lingering racism, of painting and a murder — culminating in a contemporary clash over an artistic legacy.

Only loosely allied, they are credited with churning out some 200,000 landscape paintings in the area of Fort Pierce, Fla., since the 1960s. The strategy behind their enterprise: Paint a lot, and paint fast. Often, the oil paintings were sold before they had even dried. And a teenager named Alfred Hair was the mastermind behind the whole operation.

Jim Crow was effectively lingering in 1960s Fort Pierce, which was literally segregated by train tracks and was the site of Ku Klux Klan marches. Job opportunities open to young men like Hair were limited. But after a field trip to the successful studio of artist A.E. Backus, Hair knew just what to do.

Backus, to give some background, was "the dean" of the Florida landscape school, or Indian River school. His romantic paintings, in the tradition of John Constable and compared to John Singer Sargent, give the viewer all the lushness of Florida's promise. Backus sold thousands of paintings to collectors.

And Backus was exceptional in other ways, too. He kept his studio doors open to everyone, including people of color, and all kinds of people came. He loved jazz. He was friendly with Harlem Renaissance author Zora Neale Hurston, who spent her last years in Fort Pierce. And he gave the young Alfred Hair a job stretching canvases.

Soon enough, Hair himself was painting.

Hair, James Gibson and a handful of others soon hit on an irresistible marketing strategy: They would paint all day, and hire friends to sell the paintings along Route 1 — since, after all, they weren't allowed in galleries. The paintings were dreamy, Eisenhower-era landscapes of what everyone hoped Florida would be.

These painters were young, in their 20s. They worked hard and played hard. There was the dog track, there was car racing, and there were women. No one lived like The Highwaymen, the envy of their peers. And there was rivalry.

"He was very easy on the eyes," says Doretha Hair Truesdell, who married Hair in the 1960s.

Alfred Hair, one of the original Highwaymen painters.

And it was Hair's success and good looks that would lead to his demise. As is often the case, the legend varies depending on the storyteller. But in short:

On a fateful summer day in 1970, Hair asked Doretha if she would object to him grabbing a beer with another Highwayman. At the local bar, a jealous patron believed Hair was seeing his girlfriend and shot him in the chest; he died at 29.

That episode had the rest of The Highwaymen reeling. Their enterprise nearly died with Hair, and the market for their paintings all but dried up as tastes changed.

Recently, the publication of a few books has led to a renaissance. Paintings by The Highwaymen can command thousands today, and owners include Michelle Obama and Steven Spielberg.

Zanobia Jefferson, now 83, is the teacher who, back in the 1960s, took Alfred Hair to the Backus studio on a field trip. "I never knew, or had any idea, the far-reaching effects of that trip," she says.

It was a trip that inspired a movement, a business, an aesthetic. To this day, tensions are high between the A.E. Backus estate and The Highwaymen: Whose vision of Florida is it, really? Who should get the credit — and the money?

The truth is, the Florida of these paintings, be they by Backus or The Highwaymen, is a fast-disappearing Florida. The paintings preserve a memory of what was. And the landscape has inspired an amazing American legacy.

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