top of page


b. 1939

Willie Reagan was born in Lake Park, Florida in 1939 and moved to the small town of Gifford in 1944. It was in Gifford that he attended school and gained an interest in art. It’s said that in his younger years he was a paperboy, and he used to deliver papers on his route to a neighbor painting in the yard from time to time. This neighbor would give him tips and show him techniques, only using a palette knife and no brush and selling paintings for $20-25. This older gentleman was named Harold Newton.

While Willie enjoyed painting, it was not a job for him. He was a talented athlete, and after high school he left to attend Florida A&M on a four year scholarship to play football. He graduated with a B.A. in Art Education and moved to Savannah to teach. He taught for one year before being drafted into the army, and then two years later returned to Indian River County with his wife Don DeLora. 


When he returned to South Florida, he reconnected with friends such as George Buckner, Ellis Buckner, and Alphonso Moran. His passion for painting was reignited once again, and he began painting on a regular basis. He would do so with his friends, but was also very driven and eventually went out on his own. Willie says that his only Highwaymen teacher was Harold Newton. 

During the years in which interest in Florida landscapes waned (1980s-2000’s), Reagan took a 22 year hiatus from painting. Once retiring from teaching in Indian River County, he decided to return to painting and continued his quest to become the premier Highwaymen painter. Reagan still continues to paint and is an active member of the Highwaymen community today. He attends shows and events and offers paintings, prints, and giclees for buyers of all price-points.

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 Since the site is no longer active, we have provided them here.

bottom of page