Assessing the most valuable Highwaymen paintings

The most valuable Highwaymen paintings have this in common: Harold Newton and Alfred Hair Jr. While the original Florida Highwayman group consisted of 26 members, one of whom was a woman, Mary Ann Carroll, Newton and Hair were the best. They had the most talent and their paintings bear that out. Among the few Highwayman paintings that sell in excess of six figures, those that do are usually by Newton or Hair.

Another attribute of the most valuable Highwaymen paintings is subject matter. The Highwaymen were landscape painters. They depicted rural Florida beach scenes and interior areas of the state contemporary audiences would associate with looking like the Everglades. They painted nocturnes – nighttime pictures – sunsets, and crashing waves. Most valued among collectors, however, are images of Poinciana trees.

If you don’t have a poinciana painting, you don’t want any money,” Alfred Hair’s son Kelvin told me, repeating a common saying among the Highwaymen painters and their descendants.

The most valuable Highwaymen paintings are going to feature Poinciana trees more than likely.

One especially rare category of Highwayman paintings exists, however, even more valuable than the Poinciana trees and that is paintings with figures. Highwayman artists didn’t regularly put people in their pictures. Those that have them are particularly sought after.

Roger Lightle holds a Highwaymen painting in a storage closet in his house.
Roger Lightle holds a Highwaymen painting in a storage closet in his house.

As with any other type of painting, condition is critical. The most valuable Highwaymen paintings are in great shape with no paint loss, no fading from overexposure to the sun or frayed edges. They’ll have signatures, which many Highwayman paintings don’t have, even original authentic examples.

The most valuable Highwaymen paintings are large. Large being relative. Anything over 40-inches vertically or horizontally is large for a Highwayman painting. That is nothing when compared to the Abstract Expressionist artists – Jackson Pollock and his contemporaries – whose canvases regularly reached six, seven, eight, 10-feet or more on one side. Remember, though, the Highwaymen were also businessmen. They were painting to make a living. No one was looking for an 8-foot painting to hang over the couch or behind the receptionist desk. The Highwaymen painted to eat and needed to sell a lot of paintings to do so. Their prices were cheap – $20 – so they painted fast to produce in large quantities and they painted at a scale for which there was consumer demand. That demand was in the 30-to-36-inch range; anything markedly larger than that will be prized.

Because the Highwaymen painted in such extraordinary volume – there are likely over 200,000 Highwaymen paintings just from the original group – individual paintings are not that expensive, even good ones. Still today, a large, authentic, Florida Highwayman painting from an original member in good condition can be purchased for less than $5,000. You can’t say that about many genres in art.

Of course, the best of the best Highwayman artworks can sell in excess of $10,00, $50,000 or even $100,000, I’ve heard of people offering, and being turned down, $200,000 for Highwayman paintings, but again, those will almost exclusively be by Harold Newton or Alfred Hair and generally come from the 1950s or very early ‘60s.

The retail market for original Highwaymen paintings from the group’s golden era, the mid-50s through about 1980, has definitely picked up since they were inducted into the Florida artists Hall of Fame in 2004, but when compared to other prices for exceptional, modern and contemporary art, Florida Highwaymen paintings are still inexpensive. That’s one of the aspects which makes collecting them so enticing and why many of the Highwaymen super collectors have hundreds of paintings. No one, no matter how rich, could pull that off with, say, the Impressionists, or the Abstract Expressionists, or the famous names in Pop art, individual examples of which can sell for over $50 million and regularly do.

If you’re looking for the most valuable Highwayman paintings, look for Newton, look for Hair, look for figures, look for signatures, look for size, look for condition and look for the 1950s. Good luck.

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  • Jason rickner
    April 28, 2023

    Have a 36/24 0il by M.A.Carrol looking for the value of it been on my wall since 1990

    • Chadd Scott
      April 28, 2023

      Highwaymen Art Specialists in Vero Beach and online are the leading experts at valuation of original Highwaymen art. Contact them here and ask for Roger: