My favorite Highwaymen paintings are wind-swept beach scenes. I’m in the minority. Most other people’s favorites are Florida Highwaymen poinciana paintings.
“The poinciana is the biggest seller, and what we say in the world of Highwaymen, when it’s just a group of us and we’re talking amongst ourselves, ‘if you don’t have a poinciana painting, you don’t want any money,’” Kelvin Hair told me when he appeared as a guest on my “Welcome to Florida” podcast. “The Highwaymen have gotten known for painting the poinciana. I don’t know of any collector, or anyone who has Highwaymen paintings… that has two or more and none of them is a poinciana. Almost everybody, their first one, they want a poinciana.”
Native to Madagascar, royal poinciana trees are known for their showy flowers. Because the poinciana tree doesn’t take well to frost, it’s primarily found in South Florida, not much further north than the Highwaymen’s historic home base of Ft. Pierce in St. Lucie County about midway between Daytona Beach and Ft. Lauderdale.

While Florida Highwaymen poinciana paintings were produced in great number by all members of the group, perhaps the greatest singular example comes from Harold Newton. Roger Lightle, owner of Highwaymen Art Specialists, Inc., proudly displays the 1958 painting with original green frame in his home. The crown jewel of his Highwaymen art collection greets visitors upon entering the front door.
What makes it so good?
“It’s in the right era, it’s by the right artist, it’s on canvas which is extremely rare,” Lightle said. Most Highwaymen paintings were produced on Upson board, a cheap construction material used to keep their costs down. “Why did (Newton) paint (this painting) on canvas, because it’s a special painting.”
Perhaps the best painting ever produced of the Highwaymen’s most iconic subject from the group’s most heralded practitioner at the height of his powers. All the attributes of the most valuable Highwaymen paintings. Lightle has turned down six-figure offers for it.
“I’ve seen a lot of these paintings,” Lightle, whose collection exceeds 500 Highwaymen artworks, said. “I’m very aware of the important paintings and the skill level that Harold Newton had in that era to paint that well.”
Newton began painting in 1954 and by 1958, the year Lightle’s picture was completed, Newton had mastered his technique. Four years may not seem like a long time, but remember, the Highwaymen were volume painters, sometimes completing more than 20 a day. Of those, many would have been Florida Highwaymen poinciana paintings.
“It is a poinciana, it is a scene that was painted frequently. Why? Because it sold,” Lightle says. “That was a painting they could count on painting and selling. They were working artists, they painted to survive.”
In addition to housing his best-in-class collection of Highwaymen art heavy on top practitioners among the group’s “original” members – Harold Newton, Alfred Hair, Willie Daniels and R.A. “Roy” McLendon – Lightle’s Vero Beach home also doubles as headquarters for his business, Highwaymen Art Specialists, Inc. Lightle buys and sells Highwaymen artwork from around the nation, but his greatest passion is as a collector and storyteller of the group.
Lightle welcomes visitors to see his collection upon making an appointment through the business website.

Life lessons from the Florida Highwaymen
The Florida Highwaymen teach lessons about business through their sales practices. They teach lessons about innovation through their painting methods. They teach lessons about American history through the obstacles they overcame.
Perhaps more even than their magnificent paintings, however, the Florida Highwaymen should be admired for their perseverance.
“One of the legacies and lessons you can learn from (them), me being a Black man, is no matter what obstacles you face, find the way around it,” Kelvin Hair said. “They were facing a lot of obstacles: you couldn’t get in the art gallery, you can’t get a museum, you can’t sell your painting for much. They found a way around all of those. OK, I can’t sell a painting for much? I’ll paint faster and sell it cheaper. Can’t sell in an art gallery? I’ll go sell door-to-door. They just kept finding a way around the obstacles.”
And the Florida Highwaymen just kept painting poincianas.
Alfred HairFlorida HighwaymenHarold NewtonKelvin HairRoy McLendon
Anita Mclaughlin
August 30, 2022Very interesting I had some for sale a couple of weeks ago prices to though I didn’t take it… Should you buy from that living last highwaymen alive now ????
Chadd Scott
August 30, 2022If you love the work and can afford it, sure. Only buy art you truly enjoy, not because you think it may appreciate in value.