He received his bachelor’s degree in art education in 1963 and was hired to teach in Savannah, Georgia. He taught there for one year before being drafted into the army. In 1965 he married Don DeLora; they have now been together for almost 50 years.
Willie started painting Florida landscapes in 1966 after he left the army. Harold Newton, who was a little older, had inspired him years ago when he was a paperboy and used to bike past him as he was painting. Willie explains, “Harold put a board up on the side of his house and would paint with a palette knife. I never saw him use a brush. Then he’d sell them for $20-$25, which was a lot of money at that time.”
Like the other painters he knew, Willie discovered they would sell. He knew Alfred Hair painted fast and had fancy cars, but Willie was more practical. 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.
Willie Reagan mostly painted alone and sold alone, although he occasionally worked with his friends George and Ellis Buckner. When selling, he’d knock on doors in new housing areas. He knew that people who had just purchased a house would probably need paintings for their walls. He’d have a small painting in his hands when someone opened the door and would ask if they were interested in buying art. They would usually inquire if he had more and Willie would take his paintings out of the car and lean them up for viewing. He’d usually sell a few after holding them up on walls for his prospective customers to see how they looked. He did really well selling this way.
He was making $300 to $400 a week when he got a call asking if he wanted to teach in Gifford. He wasn’t sure he wanted to give up his life as a painter so he asked his mother for advice. She thought he should teach since his college education prepared him for this line of work, but she emphasized that the decision was his. He gave up painting and started teaching once again. He taught at Gifford High School for two years, Vero Beach High School for three years, the Learning Center with 8th and 9th graders for sixteen years, and then he worked 6th graders in middle school for seven years. As a teacher, he was a strong disciplinarian. He believed that if students were going to be in his class, they were going to learn something. His gift for teaching, he says, is “a gift from God.”
After retiring in 1995, he slowly returned to landscape painting. Once the Highwaymen had been named and their landscapes became popular again, he exhibited his work—about ten paintings—and sold all but one in two hours. It was then he thought, “It’s time to seriously get back to painting.” But he still took his time doing so.
Willie and Don have lived in the same house in Vero Beach for over forty years. It is a large house with a good-size studio space that has also served as a rental property. Willie did all the carpentry work in the house except for the kitchen cabinets. Being good with building things, Willie explains, is a “major gift.” He has a number of rental properties, which he fixes up for additional income.
He and Don have two children, Darrin and Joy. His son, who lives in Atlanta, is in construction; his daughter is an elementary teacher who is married to a vice-principal. They live north of Tampa. Both his children went to Florida A&M. Willie appreciates his education and wanted to pass that value onto his children and his students. But he’s quick to give credit to Harold Newton for what he taught him. “He was able to just pull these scenes out of his head. I learned more from him than I learned in college. This was simply from watching him work. He painted what people buy.” Willie says that Harold was his only Highwayman teacher, although he has a lot of respect for Robert Butler’s work, mostly because he gave dogs, hogs, and other animals real character.
His studio is filled with his paintings and those of other Highwaymen. Some of his most prized works are an early painting by Harold Newton, one by Alfonso Moran, and one by his old friend George Buckner. He purchased all three from the same person, as he wanted to own some early Highwaymen work.
While he is proud of being a Highwayman, he wasn’t driven by making money from painting the way Alfred Hair and Al Black were. He remembers that he and Don went to Alfred’s house one time to watch him paint. Alfred lined up about six boards and painted them really fast. Willie was unimpressed. He wanted to paint good paintings, not fast ones. Money, he explains, doesn’t excite him. It was more important for him to do something useful with his life and painting fast in factory style didn’t make sense to him. He also didn’t drink beers with the other painters; instead, he did his moderate drinking at home. It was Harold Newton who was his inspiration. And Bean Backus, who he met in the late 1960s, impressed him as an artist. Willie notes that there are other well known Highwaymen who he didn’t meet for decades. For example, he didn’t meet James Gibson until 2003.
These days Willie can often be found painting. He always has a good number of paintings ready for an exhibition and can pull a show together at a moment’s notice.
There are also other interests that demand Willie’s time. For example, he enjoys taking care of his yard. A few years ago he planted a Poinciana tree, the Highwaymen’s trademark, bright red tree. “It hasn’t bloomed yet,” he says, but he hopes that it will soon.
Unlike most of the Highwaymen, Willie will sometimes paint still lifes. He figures he’s an educated artist and that’s what educated artists do. He paints other things as well. Sometimes he places small figures in his work. He has a car in one scene and he occasionally paints two owls based on a magazine picture he likes. Likewise, a photograph inspired a painting of a place in China, a country he’s never been to.
But Willie’s scenes are often specific places he’s been to. Because Don worked part time as a travel agent, they were enticed to take several exciting trips. He has paintings of Alaska’s Inside Passage, Paris, Jamaica, and state parks in Florida such as Wekiva Springs and Stephen Foster. He’s painted Tampa Bay’s Skyway Bridge several times, although he’s terrified of crossing it. (He’s afraid of heights and that includes driving on mountains.) He can tell you the names of the trees he paints, including each kind of palm.
He has an easel in his studio where he works on one canvas at a time. He never works in a series the way Alfred Hair did. And he doesn’t rush; he is compelled to do a good job.
Several years ago, Robert Butler set up an experience for Willie and a few other Highwaymen at Wekiva Springs State Park. Willie had always been a coastal painter who liked working with the horizon line and the sky. When he first painted Florida’s interior, which Robert most often did, he found that it could be midday and there might be so much foliage that you couldn’t see much of the sky or a clear horizon line. These kinds of scenes made him rethink his creative process.
These days, Willie buys most of his frames and sells primarily to snowbirds. They always seem to want the same subject matter: the Florida landscape. When he paints a scene he likes, he often paints it again. He does not consider the second or third painting in the series to be an original even though it is painted individually. He explains this to his customers, as he thinks people should know. Willie’s knowledge of art conventions continues to inform his work in ways that mark his individuality.