Having earned a bachelor’s degree in art education from Florida A&M University, Willie Reagan imparted traditional artistic values to his public school students; like a few others he had fulltime employment and painted as an aside. Reagan favored Harold Newton’s skill-based painting over the fast-painting style of Alfred Hair and others in his orbit.

Reagan’s sales technique was somewhat different from that of other Highwaymen. Whereas they typically went to business offices along Florida’s east coast to vend their paintings, Reagan preferred knocking on the doors in new housing developments and greeting residents with a painting in hand. If they expressed interest, he would ask them to look at a selection of paintings that were in his car, even offering to hang their purchases for them.