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Born in Jacksonville, Florida, Sylvester always liked to draw. Although no one in his family was artistic, he spent his time drawing, beginning at the age of six. On his own, he developed skills in portraiture and sign painting. After finishing high school in Jacksonville, he joined the army and was stationed in France. Once his service was completed, he returned to Jacksonville and ended up in Cocoa Beach, Florida where he became friends with another local artist named Robert Lewis.

One day when he was 25, Sylvester was walking on the main street in Cocoa and met Alfred Hair. Alfred was carrying a stack of landscape paintings into a bank to sell. Sylvester admired the artwork and struck up a conversation with the artist. Sylvester asked Alfred if painting was the only thing he did for a living. Alfred replied affirmatively and added, “That’s why I’m driving a pink Cadillac” (The car was parked on the street.) As Sylvester studied the paintings, it came to him that painting landscapes would be his job. Sylvester was already painting portraits and signs for a long time. Now he would learn to paint landscapes.

Sylvester went home and told his wife Consuelo, “I’m going to paint for a living.” She looked at him strangely. This revelation didn’t make sense to her, but she trusted her husband and wanted to support him.

He knew he needed to find someone to teach him. He had heard that there was an artist named Harold Newton painting landscapes in Cocoa. So he “put out the word” that he wanted to talk to him. They finally met and Harold told him he could watch him paint. He learned the tips and tricks when it came to painting, such as the Upson board and crown molding frames to cut costs. He returned to Cocoa with a new business proposition for his friend, Robert Lewis.

His best critics were his customers. They would offer helpful suggestions, which Sylvester took to heart. They made him a better painter. He also learned from Robert Lewis (fellow Highwaymen) who was also painting and living in Cocoa at the time. Like the other Highwaymen, he took his paintings on the road, selling up and down the highways on the east coast of Florida. He painted and sold his works on the roadways for forty years.

Painting isn’t the most important part of his life; preaching the gospel was his primary mission. He didn’t study in a Bible school until he was 72. He mostly learned by listening and reading the Bible. Although he never had a church, he was a Seventh Day Adventist. But, he believed that it doesn’t really matter what religion you are; what’s most important is how you live your life.

Wells passed in August of 2023. He stopped painting many years ago as he began to blind from glaucoma. He never saw Alfred Hair again after that first meeting at the bank in Cocoa. And he said, he had never been to Fort Pierce. Trusting in God’s message that he had a talent that should be developed, he made his living through art.

Biographies are adapted from those on, one of the earliest informative websites on the Florida Highwaymen. Since the site is no longer active, we have provided them here.

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