Willie was raised in Fort Pierce, along with his younger brother Johnny who was also a Highwayman. Willie was always interested in art, and as a young boy, he created his first painting on a cigar box. Lincoln Park Academy art teacher Zanobia Jefferson remembers that he once painted a scene for Ms. Johnson, the home economics teacher, at her request. Willie worked as a day laborer in the citrus groves and packinghouses. It was difficult work for little pay, which made the lives of the painters he encountered seem all the more glorified.
Mary Ann Carroll lived three doors down from his family home and Newton and McLendon later became neighbors. Willie had strong relationships with Livingston Roberts and Al Black; he enjoyed the friendly competition and camaraderie with the landscape painters he knew. Like other Highwaymen, Willie learned by watching. By the mid-1960s he was creating his own work. He emulated Harold Newton the most. “Harold was number one,” he once claimed. “Everyone wanted to be like him. Masterpieces off the top of his head.” After painting his own works, Willie would show them to Harold for feedback. But Harold rarely critiqued anyone’s work. The most advise Willie ever got from Harold was to lower his horizon line.
Working with Livingston, he began making ten to twelve paintings every night. Al Black was usually the salesman. In the early days, Willie often didn’t sign his work, so Al painted in his name thinking he could get more money as the artist and the seller. Later, Willie began signing his own work with a nail.
When riots broke out in Fort Pierce on April 8, 1968 after Martin Luther King, Jr.’s assassination, Daniels was arrested for a curfew violation. He was a young man during the Civil Rights Movement and he felt the rage of racism. Like others in his community, he wanted a better life and was willing to work for it. However, a demand for landscape paintings faded in the 1970s and Willie had to find other work.
When Jim Fitch published his article in the 1993-1994 issue of Art and Artists of Florida naming the Highwaymen, Willie was working as a truck driver in Augusta, Georgia, although he was still painting. He was unaware of his recent fame and didn’t know his friends were now making hundreds of dollars for a painting. His boss, however, was more attentive to Willie’s notoriety as a Highwayman and began purchasing his paintings for $35 a piece. Willie returned to Fort Pierce in 2001 and once again began painting full time. He was shocked and pleased to find such enthusiasm for his work. Like many of the other painters, he began creating his landscapes more slowly and carefully, with the goal of making excellent work.