Along the way we visited a few antique stores that carried his paintings on consignment. In one of them, his work had already been sold out. The proprietors spoke of him with genuine affection — a local legend, a living tradition, complete with its own myth and lore.

But the place he most wanted to show us was the water. It was one of his favorite places to paint.

Eventually, we stood on the banks of the Indian River Lagoon, where the larger story began to take shape.

Standing along the river, Mr. Sears explained how artists from Gifford and nearby Fort Pierce began painting Florida’s landscapes in the 1950s and selling them along highways and door-to-door because segregation kept them out of traditional galleries.

They loaded their paintings into their cars and traveled from town to town selling scenes of Florida’s skies, palms, rivers, and coastlines.

What began as survival became one of Florida’s most important art movements.

Mr. Sears spoke about Harold Newton, one of the artists who helped define the movement. According to him, Newton’s work revealed something powerful — a style of landscape painting emerging from Florida’s Black community that the art world had never really seen before. Those luminous sunsets, winding waterways, and leaning palms would eventually define the Highwaymen style.

And as Mr. Sears made certain to clarify that afternoon, the roots of that style trace back to Gifford.

Standing along the river, you could see the light in his eyes when he talked about it. He didn’t describe the Highwaymen like distant figures in a history book.

He spoke about them like family.

At one point in our conversation he shared that he had been battling a serious illness.

Even then his spirit remained light. His laugh was easy, and the story he cared most about — the legacy of the Highwaymen and the role Gifford played in shaping it — remained at the center of everything he talked about.

After that visit we stayed in touch. From time to time he would send updates about his paintings, the art world, and the documentary he continued to champion. Somewhere along the way our conversations became familiar enough that I started calling him Unc — short for uncle — and he seemed to accept the title with a smile.

The last time I reached out to him was to ask his opinion about a painting a friend had posted online. The piece wasn’t signed, but the style looked unmistakably familiar — the kind of landscape that carried the visual language the Highwaymen made famous.

This time, Mr. Sears didn’t answer.

Instead, his niece replied.

That’s how I learned he had passed.

Only later did I realize how rare that encounter had been. History doesn’t always arrive in grand moments. Sometimes, it makes itself known in simple conversations, with people who carry it quietly.

In the short time I knew him, Michael Sears showed me more than paintings. He opened a window into a piece of Florida history — one rooted in resilience, entrepreneurship, and the determination of artists who created their own path when the traditional art world shut them out.

The original Highwaymen painted Florida’s landscapes and sold them along highways because the gallery doors were closed to them.

Standing along the banks of the Indian River in Gifford, Michael Sears told that story with the calm certainty of someone who understood exactly where he stood inside it.

Others called him a legacy artist.

He shunned that title.

In his mind, he was exactly what those painters had always been.

A Highwayman.

Editor’s Note:
During our visit to Gifford, Pulp City Magazine recorded an extended interview with Michael Sears about the history of Gifford and the Florida Highwaymen. We hope to share that full conversation in the future, with the family’s permission, so Mr. Sears can tell that story in his own words.