The Day I Chased Away The Highwaymen

by Mike Miller
(Mount Dora, Florida)

Highwaymen Shack

Highwaymen Shack

I went to school to become a civil engineer. There were no art appreciation courses for engineers back in the days I attended the University of Florida. What little art education I have was learned the hard way: by making dumb mistakes.

One of the dumbest mistakes was back in the 1970s.

I owned a small engineering firm in Indialantic, Florida. Our office was on State Road A1A in a salty old motel directly on the ocean.

My drafting and design staff were all surfers, and their favorite lunchtime pastime was grabbing their boards and surfing in the ocean right in front of our office.

Sometimes it would take a little extra encouragement to induce them back to work and a bunch of extra coffee to keep them from taking a nap.

The drafting room looked like a miniature version of Ron Jon's Surf Shop with brightly painted surf boards and wet suits hanging all over the walls. In spite of the festive environment, we got a lot of work done. But I certainly didn't need any more distractions.

One afternoon I came back to the office and saw my staff gathered around a big old rusty car in the parking lot. The trunk was open and two black men were holding up objects and showing them around. When I got closer I could see the men were trying to sell paintings to my staff.

On my time.

The paintings were on cheap particle board - Masonite or Upson board - and portrayed Florida scenes of palm trees waving in the wind, roiling surf crashing on the beach, various beach side shacks and tropical trees with blossoms of red and every other primary color.

I did not recognize it as art, but as just another distraction keeping my always fun loving staff from their labors. I chased my people back into the office and strongly advised the black men to pack up and move on.

They offered no argument, quickly packed up and drove off to their next destination. I had the feeling they were accustomed to being chased off properties.

It was some years later when I realized that I had chased a couple of the now famous Highwaymen off my parking lot. Some of those paintings I didn't appreciate back then are worth thousands of dollars today.

I cry every time I go to one of Florida's Highwaymen art shows and see what I failed to recognize as art back in the day.

Comments for The Day I Chased Away The Highwaymen

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May 18, 2020
Purchased in Ocala
by: Anonymous

James Gibson took his art into my father’s office bldg in the ‘60s. He bought one with the paint still wet. I still have it in my living room.

May 18, 2020
Lake Okeechobee, Lakeport
by: Anonymous

When I was a lot younger in the early 1970’s, one of the Highwaymen came by several times sell his paintings out of the back of his Dad still loves those paintings to this day.

May 18, 2020
Highwaymen Art
by: Anonymous

Working in beauty shop was able to get some of the most beautiful ones. Still have them hanging. Still have wonderful memories of the Highway men who never gave up. Have a dream see where it can lead you.

Apr 20, 2019
I think a lot of us have a story
by: Anonymous

I worked for a company in Merritt Island that opened a office and bought some of this art from a truck.

Had no idea where they got them, but when we closed the office they were going to throw away those paintings. I did take them (after asking) as I love palm trees, it was 20 years later when someone came to my home that I was told who painted them, their value etc.

My husband actually wanted me to throw them away many times. . He thought they were cheap looking.

They still hang in my living room till this day.

Apr 20, 2019
Kelvin Hair, Alfred’s son
by: Teresa

I’ve been fortunate enough to purchase one. I recently attended a Highwaymen show and Alfred Hair’s son, Kelvin. He is an incredible painter.

He painted with his dad growing up. His paintings look like photographs. I found one I felt I had to have...until I saw the price.

It was $40,000!

Apr 19, 2019
Me too!
by: Anonymous

I worked at the Agricultural Center and they made regular stops there to sell paintings. Some bought them.

I could only think how ridiculous.

What artist would try to sell a painting with the paint still wet?

Apr 19, 2019
i bet the survey crew were huffing the herb
by: Anonymous

Sad, but hey ..... art is so subjective.

Show the unenlightened a Picasso and they'd not understand.

I mean, who knew?

Apr 19, 2019
My Late Father Bought one I still have
by: flacorps

My late father, neither an art afficionado nor pioneer of civil rights appreciation, bought one one the streets of Tampa in the 1970s.

A Sylvester Wells seascape.

I still have it.

Feb 16, 2019
Glad I Stopped
by: Anonymous

I acquired my first 3 Highwaymen paintings from a car trunk alongside US1 in Ft Pierce many years ago.

Two were black and white James Gibsons (he did very few of these) and a Sam Newton.

I've been fortunate to acquire 3 other Highwaymen paintings through the years.


You were smart. I was not! Congratulations.

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