In the 1960s, Alfred Hair and his friends were producing paintings like no tomorrow. The Highwaymen needed salesmen. One day Al Black gave art sales a try. Soon he quit his job cleaning typewriters and was moving oils before the paint had time to dry. Stories of his sales prowess are legend. He was the Highwaymen’s million dollar man.

By dint of his charismatic personality as well as talent, Alfred Hair was a leader among the Highwaymen artists. Al Black, his star salesman, remembers the night in 1970 when Alfred was shot and killed in Eddie’s Bar. He was 29.

When blacks of her generation weren’t allowed to sell their art in galleries — and black women of her generation worked as teachers, babysitters or fruit pickers — Mary Ann Carroll painted alongside Harold Newton, Alfred Hair and other segregation-era landscape artists who later became known as the Florida Highwaymen. Art supported her when she was raising her children as a single mom, and continued to support her through her life. She is the only woman in the group termed “the original” Highwaymen, honored in the Florida Artists Hall of Fame. This video is part of a longer interview recorded in Ms. Carroll’s Fort Pierce home in 2014.

Art historian Jim Fitch is credited with coming up with the name The Highwaymen to market Florida’s black landscape artists. While not all the artists approved of the name, Fitch brought them to the attention of serious art investors for the first time.

After college, James Gibson came home to Fort Pierce where Alfred Hair and Harold Newton taught him to paint. He also became a successful marketer — one time, convincing a menacing state trooper to buy three of his oils. For 55 years, Gibson continued to show and sell his paintings. His work hangs in the White House. Mr. Gibson passed away on August 13, 2017, at age 79.

Doretha and Alfred Hair lived the artists’ life, surrounded by their painter friends and the rising African American musicians who passed through Fort Pierce playing the Chitlin’ Circuit. Doretha made Alfred’s frames and learned to paint. Then, in an eyeblink, that life was over.

As a girl, Zanobia Jefferson studied art with the luminaries of the Harlem Renaissance. When she began teaching at all-black Lincoln Park High, Fort Pierce’s renowned painter A. E. ‘Beanie’ Backus reached out to her students across the color divide. A door opened in their minds. Ms. Jefferson died January 2, 2017, at age 89.

Highwayman artist Willie Reagan went to college on a football scholarship and became a successful landscape artist by keeping his eye on the prize.

God gave Charles Walker talent. His parents gave him love. Dedication did the rest.