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Hair is often regarded as the most influential member of the Highwaymen group. He is described by Gary Monroe (the most prolific author on the Highwaymen) as “The Heart of the Highwaymen”. His story is also perhaps the most compelling. 

Alfred Warner Hair was born in Ft. Pierce, Florida in 1941.  Growing up in Fort Pierce, He, like most of the artists, had very limited options for making money during a Jim Crow era South Florida. Most kids at the time would pick oranges in the groves, which was a very hard earned day's wage at the time. Hair wished for more, and out of this drive, he created the legacy that is the Highwaymen. 

It all started when Zanobia Jefferson, Alfred’s art teacher at Lincoln Park Academy, recognized Hair’s talent artistically. She is the one who introduced him to Bean Backus, the white Florida landscape painter who would mentor Hair in his early years as an artist. While most of the Highwaymen artists spent time in Backus’ studio and watched him, Hair is the only member who took formal lessons from Backus. He and Backus grew close over the years, even getting the chance to accompany Backus on a trip to Jamaica when he went there to paint. Many of Hair’s earliest paintings are very skilled and reminiscent of techniques learned from Backus. While this may seem counterintuitive, it was because of a key fact that would shape Hair’s career entirely. 

At the time, Backus was primarily painting on commission, and a typical Backus painting would cost a few hundred dollars (a decent amount of money at the time). Hair knew that he would never be able to sell paintings at that price point, not only because of the niche buyer base, but also due to racial barriers he would never receive representation in a gallery. Hair’s business savvy provided a solution: rather than spending six hours on a single painting that would sell for $300.00, he knew he could paint ten paintings in that time and sell those for $30. Knowing they would be lower quality, his target audience was no longer the rich and wealthy, but the average American. Now all he needed was a way to sell them. 

Alfred at this time knew of another artist that had success painting Florida landscapes under Backus, who had been selling paintings on his own. Very skilled, yet selling inexpensive art to local Floridians and tourists. He heard that the artist would go door to door and along the roadside of A1A, venturing into businesses to inquire about selling paintings. His name was Harold Newton.

Hair adopted this method himself and got to work. His goal, as told by many of those who knew him, was to be a millionaire by the time he was 35. He would paint ten, twenty, or even thirty landscapes a day and sell them for $25-35 depending on size. Certainly better than a day in the orange groves. That was not enough for Hair though. If he was to meet his goal, he needed to be painting more, and selling more. So he started recruiting others to join him. Friends, neighbors, and anyone who was eager to learn and make some money. Of these earliest recruits include some familiar names to the group, such as Livingston Roberts, James Gibson, and Al Black (the salesman). This is how the group started to form. 

The Highwaymen story however drastically changed on August 9th, 1970. At the time, many of the artists would meet up at a place called Eddie’s Bar in Ft. Pierce to discuss the day’s sales and divide up earnings. On this night, Alfred went to the bar with Livingston Roberts and was shot and killed in a bar fight. The tragedy caused a disbanding of the group for many, leaving to mourn the loss of their friend and never returning. 

The market began to fall off in the following years leading up into the 1980’s when the desire for Florida landscapes dissipated. It was not until the mid-1990s when the Jim Fitch article was released that the artists gained any fame, which Alfred was unfortunately not around to see. His work and brilliance began to receive the respect it deserved following this, and in 2004 he was inducted into the Florida Hall of Fame. His legacy continues to this day as he is recognized for his skill, entrepreneurship, and impact as the “Heart of the Highwaymen”.

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