Picture a wet oil painting drying across the back seat of a car while parked somewhere along Florida’s Atlantic coast. The canvas glows with an electric orange sky as palm trees bend with a wind born from the artist’s imagination. And his fingers, well, they still carry the colorful evidence of the previous days’ work.
This is just one depiction of the life of a Florida Highwayman, part of a group of Black men and one Black woman who built an independent art economy from the 1950s through the 1980s, under the shadow of racial segregation.
Excluded from established galleries amid the racial mores of the day, the Highwaymen refused to wait for recognition or permission. They loaded their Florida landscapes into their cars and sold them directly to businesses, tourists, and homeowners along the state’s highways, sometimes while the oils were still wet.
I have spent much of my life thinking about freedom as something practiced through the body, the mind, and the daily choices we make about our labor. The Florida Highwaymen understood what has taken me decades to learn: freedom often begins before the world agrees that you are free.
Who Were the Florida Highwaymen?
The Florida Highwaymen were largely self-taught landscape painters, who began capturing Florida’s wild beauty in the mid-1950s. Their work featured beaches, marshes, moonlit water, and the fiery blooms of the royal poinciana tree. Between the mid-1950s and 1970, they produced an estimated 200,000 paintings, sometimes dozens in a single day.
I have long found myself moved by their story because it exemplifies what people can build through voluntary cooperation when established institutions and societal practices refuse them entry.
The Smithsonian’s own account puts it plainly: the Highwaymen “leveraged their entrepreneurial spirit to create an independent artistic tradition during the era of segregation,” turning painting into “an alternative livelihood” to the region’s exhausting, poorly paid labor.
A.E. Backus, Alfred Hair, and the Door That Opened
The origin of the Florida Highwaymen is closely tied to A.E. “Bean” Backus, a respected white landscape painter from Florida’s Fort Pierce area. Backus met with two aspiring Black artists, teenager Alfred Hair and Harold Newton. According to the Backus Museum, the encounter “kindled” in Hair the possibility of an artistic path “beyond the prevailing racial barriers of the times and toward a brighter, self-made future.”
Hair absorbed his mentor’s lessons without becoming an imitation of him. He adapted what he learned into a model of his own, then built a network of painters, framers, and salespeople who recognized their collective power to create, sell, and prosper on their own terms.
How the Florida Highwaymen Built a Roadside Art Economy
In Taoism, pu, the uncarved block, symbolizes our original potential before the world shapes us into something approved and recognizable. I have long been struck by how the Highwaymen entered an art world obsessed with credentials, gatekeepers, and permission. Yet they preserved enough of that uncarved spirit to imagine another way.
For the Highwaymen, limited funds became an invitation to improvise. Because traditional canvas was too expensive, they painted on inexpensive, often discarded Upson board. When professional framing remained beyond their reach, they fashioned frames from scrap crown molding, painted them gold or silver, and made them deep enough to stack paintings while the oils were still wet.
I recognize something of my own life in that uncarved block. By my mid-twenties, I had held executive positions at three hospitals and a community health center. Then, in 1993, I walked away without a polished plan for what would come next.
Years later, I found myself unhoused for a brief period in California and Nevada. During that stretch, it became apparent to me that my résumé or how important I had once appeared inside an organization weren’t what truly mattered. What remained were my curiosity, adaptability, books, relationships, and refusal to believe my story was finished. That season taught me that sovereignty often begins when we stop mourning the tools we lack long enough to recognize the ones still in our hands.
Selling Art Outside the Galleries of Jim Crow
Jim Crow was never just prejudice held by a group of disagreeable individuals. It was, as the Library of Congress documents, “a system of laws and practices” that for more than a century after the Civil War “denied full freedom and citizenship to African Americans, segregating nearly all aspects of public life.”
The Highwaymen’s success does not prove that commerce floats above racism. It reveals something more honest: voluntary exchange could still create breathing room within a system whose official rules were designed to deny them economic freedom.
Selling a painting from the trunk of a car did not dismantle Jim Crow, but it gave an artist income, mobility, and another day beyond the economic boundaries segregation had drawn. Shut out of white-owned galleries, the Highwaymen sold their work along roadsides, door to door, and directly to businesses.
Writing amid the French Revolution upheavals of 1848, Frédéric Bastiat captured the underlying instinct simply: “Let us therefore demand the freedom to trade.” The Highwaymen lived out that sentence in their own time and place. When the front door of the approved economy was bolted shut, they built side doors from whatever they had available.
What Taoism Reveals About Their Adaptability
Adaptability is where the Highwaymen’s story becomes Taoist for me. Lao Tzu returns again and again to the symbolic nature of water because it is soft without being powerless, adaptive without being submissive. “The soft overcomes the hard, the gentle overcomes the rigid,” he writes in Chapter 78 of the Tao Te Ching (Stephen Mitchell translation).
The Highwaymen were not passive, and wu wei has never meant sitting quietly while someone else draws your boundaries. It means acting without wasting your life on methods that cannot serve the moment. The galleries were closed to them, but the highway was open; canvas was expensive, but Upson board was affordable. Established collectors remained beyond their reach, but offices, motels, tourists, and homeowners still wanted the radiance of Florida sunlight on their walls.
Friedrich Hayek gave economic language to this kind of emergence when he described “orderly structures which are the product of the action of many men but are not the result of human design.” In other words, no central authority planned the Highwaymen’s roadside economy. They grew their free enterprise painting by painting, sale by sale, through repeated acts of voluntary exchange rather than a master blueprint.
Economic Independence and the Freedom to Work
I believe economic freedom is inseparable from personal sovereignty. Directing your own labor and keeping the fruits of what you create are essential to human flourishing.
Murray Rothbard grounded this freedom in self-ownership. A person’s right to control his life, he noted, “must also” include the right to sustain it “by grappling with and transforming resources,” thereby claiming ownership of the ground beneath his feet.
A painting made on scrap board and sold from the trunk of a car embodies that principle: a person transforming whatever lies within reach into something valuable, without waiting for gatekeepers to grant him better materials or access to an established market.
My own credo has long been simple: never have a boss, and never be a boss. I seek relationships rooted in voluntary exchange and mutual benefit rather than domination in either direction. The Highwaymen shared techniques, collaborated, competed, and built networks without allowing those networks to harden into another suffocating institution.
What the Florida Highwaymen Can Teach Us About Self-Government
The Florida Highwaymen are a source of continual reflection for me because their story offers such a compelling example of self-government and lived freedom. It does so by rejecting two seductive errors: the belief that personal grit alone can cure structural injustice, and the equally dangerous belief that oppressed people possess no meaningful agency until the government hands it to them. Both underestimate the human spirit and overestimate the formal system.
As Lysander Spooner insisted, “a man’s natural rights are his own, against the whole world,” whether the infringement comes from “one man, calling himself a robber, or by millions calling themselves a government.”
Rights written on paper and those exercised in daily life are not the same. The Highwaymen practiced theirs first and allowed official recognition to catch up decades later.
Self-government involves the disciplined practice of identifying where choice remains in one’s life and expanding upon it. It means governing our attention, fear, time, and creative energy before attempting to govern anyone else.
It’s knowing when to confront a wall, when to flow around it like water around stone, and when to build a door where the architect insisted none could exist. Freedom is not merely a legal status. It’s a capacity strengthened through use.
In the end, our task is not to stand at the roadside demanding certainty or waiting for government to parent us. It is to notice the boards, brushes, books, and open roads already available to us.
The Florida Highwaymen answered that challenge with their lives, carrying liberty in their hands alongside canvases whose oils were still wet. Painting by painting and sale by sale, they demonstrated that freedom can be practiced long before permission ever arrives.
