Born in Lake Park, Fla. in 1939, Willie “Bill” Reagan’s parents moved their family of 11 children to Vero Beach, Fla., around 1944. It was while growing up in Gifford, the historic African American community in Vero Beach, that Reagan encountered his first Florida Highwaymen painter, Harold Newton. Always interested in art, The Highwaymen Trail, a heritage trail organization run by the city of Fort Pierce and the Florida Humanities Council, describes Reagan’s brush with Newton as having inspired the young painter to pursue his art. Working as a paperboy to help support his family, Reagan would pedal by Newton’s house every day and see him working. “He had his paintings leaned up against the outside wall of his house and he’d be working away at them,” Reagan told the TC Palm in an interview in 2014. “All sorts of beautiful colors. Beautiful paintings. He’d be using a palette knife, just moving that paint around. I never saw him use a brush.”
But despite his talent and ambition, it was years before Willie Reagan would join the group selling their works door-to-door on the road. After high school he attended Florida A&M on a football scholarship, graduating with a degree in art education in 1963. After stints as a teacher in Georgia and some time in the army, Reagan married and settled down to life as a painter among the Highwaymen in Gifford.
More independent than the other painters in the group, Reagan typically went out on the road to sell his own work, seeking out areas of newly built housing where he knew people would be in the market for décor to fill their homes. He was also a trained artist who took his time developing his work. “He knew Alfred Hair painted fast and had fancy cars, but Willie was more practical,” The Highwaymen Trail recounts Reagan explaining. “He drove a Volvo station wagon, a make of car he continued to drive throughout his life. He notes that a Volvo is a good, solid car and it isn’t fancy like a Cadillac. This comparison suggests the difference between the personalities of the two painters.”
Following Hair’s death in 1970, Reagan continued to paint and was making a decent living supporting himself as an artist when an opportunity to start teaching again came his way. He left his career as an artist and taught art to middle and high schoolers in Vero Beach for more than twenty years, returning to painting only after his retirement in 1995.
Inducted into the Florida Artists Hall of Fame in 2004, Willie Reagan continues to live and work in the house in Vero Beach he and his wife have called home for nearly 50 years. As a formally trained artist his work is technically astute and much sought after, but he still credits Harold Newton as his greatest teacher. “He was able to just pull these scenes out of his head,” he told The Highwaymen Trail. “I learned more from him than I learned in college. This was simply from watching him work. He painted what people buy.” Known for his trademark “panoramic views” – extending his paintings onto their frames – Reagan’s work does reach subjects far beyond the traditional Highwaymen Floridian tableaux, including scenes he paints from photographs and places he’s visited including Alaska, Jamaica, and Paris.