Livingston “Castro” Roberts


1941 – 2004

Livingston Roberts’ mother believed that if you named your children after celebrated individuals, they would become successful. So Livingston was named after Dr. David Livingstone, a medical missionary who went to Africa and gained mythic status as an explorer. Known as “Castro” to his many friends because his characteristic beard resembled that of Fidel Castro’s, Roberts was outgoing and fun to be around. His personality was marked by a sensitive, generous nature, and painting was part of his life long before he came to Ft. Pierce and met Bean Backus, Harold Newton, and Alfred Hair.

Livingston was born on January 21, 1942, in     Elkton, Florida, a small town west of St. Augustine. They lived on eight acres of land purchased in 1940 by his grandmother, Gertrude Mason, a strong woman who raised five children on her own. Livingston’s mother, Elizabeth, was the youngest. Gertrude Mason made 25 cents a day cooking for laborers who cleared trees and shrubs for the construction of Highway 27.

She was paid half the wages of male loggers who labored with mules and chains. Livingston’s father, Willie, was a migrant worker until he married Elizabeth Anderson. The family grew potatoes and cabbage for a living, but their personal garden was more expansive, which included a grape arbor and a wide variety of vegetables. The family picked oranges, plums, and pecans from their fruit trees. In order to keep meat on the table, Willie and his hound dogs hunted coons, possums and rabbits at night.

Along with seven brothers and four sisters (he was the second oldest), Livingston played on the banks of the Moccasin Branch, a stream off the St. John’s River rich with old oaks and cypress trees draped in Spanish moss. He loved being in nature. His sister, Loretta Moreno, remembers him laying in the grass for hours studying the changing shapes of the clouds, a fascination with the sky he never outgrew.

During his early teenage years, Livingston’s family would visit his grandmother who moved to Miami’s South Beach after life got tough on the farm. He admired the tall coconut palms and the brightly colored hibiscus flowers he picked for his mother. When Livingston painted, he had these visual memories carefully stored in his mind. Seeking a better life, his family soon moved south to be with his grandmother.

A painting hung on the wall in Livingston’s home, and at the age of 15,  Livingston confidently told his mother that he could reproduce the image. She encouraged him to do so and Roberts went in search of house paints to meet the challenge. By all accounts it was an impressive first effort at creating a painting. A cousin later asked him to create more paintings for his home in Hallandale, Florida.

Livingston moved to Fort Pierce in 1957 to live with his grandmother, Gertrude, who was running a boarding house. He met Alfred Hair in 1961 when they were both 19 years old. They shared a passion for painting and became inseparable friends. Painting together, they would switch between Alfred’s mother’s yard on 13th Street and Avenue G and Gertrude Mason’s house at 814 Dundas Court. It was at his grandmother’s home where Livingston met Harold and Samuel Newton. Like Alfred, the two Newton brothers also became his painting buddies.


Livingston married Betty Davis in 1962 and together they had three children – Diane, Shirley, and Livingston, Jr. A few years later, he moved to Gifford, Florida, where he lived for a short time in an apartment over the Green Leaf Bar. His brother, Ernest, helped sell his paintings, while other young men in the area took note of their success. Always willing to share his talents, Livingston taught numerous painters including George and Ellis Buckner, Samuel Newton, Willie Daniels, Johnny Daniels, Jimmy Stovall, his sister, Gertrude Walker, and his brother-in-law, Charles Walker. They all considered Livingston their teacher.

Selling art was an important part of the painting enterprise, and Livingston sold many of his friends’ works along with his own. Mona Mills Walker, a secretary and bookkeeper in a Sanford medical office, remembered that in the early Highwaymen days, Livingston Roberts would come into her office a few times a year. He would line up about six paintings in their hallway for the entire staff to look and buy.


Life was good for Livingston in the 1960s. His paintings were selling well and he was surrounded by many friends. Both he and Alfred realized too late that envy and jealously of their enormous success could bring about a terrible tragedy. Everything changed on the night of August 9, 1970, when Alfred Hair was killed. They were both at Eddie’s Bar, a juke joint on Avenue D in Fort Pierce, where the painters would gather after a day of painting and selling. Alfred bought drinks for the house and played a game of pool. Julius (aka J. L., Jil or Jitterbug) Funderburk, someone Livingston had known for about eight years and considered a friend, was also there. An argument ensued and in a rage, Funderburk went to his car and retrieved a gun. Returning to the bar, he knocked Livingston off his bar stool with the gun and shot Alfred twice. Realizing what he had done, Funderburk ran for
his life.

Alfred was driven to the hospital while Livingston said he worked to keep air in his lungs. But Alfred Hair was pronounced dead just before midnight. His death weighed heavy on Livingston, as he believed he should have or could have done something differently. Lying in his clothes covered with Alfred’s blood, he cried all night.

With the vivid memory of his best friend’s death, he was unable to stay in Fort Pierce. He soon left for upstate New York to work with his Uncle Bo, a potato farmer. He and his brothers had worked the potato fields with their uncle before and Livingston had the skills to do the work. Roberts stayed for five years in Castile and Buffalo and began to heal. He continued to paint, selling most of his work in Canada. While he eventually found a way to deal with Alfred’s death, he continued to dream about it for years to come.

Before Livingston returned to Fort Pierce in 1975, his first stop was to visit his bother Ernest, who lived in Oviedo, Florida. When his painting friends heard he had returned to Florida, many came Oviedo in order to paint with him. Willie and Johnny Daniels, Harold Newton, and Al Black all lived in the Oviedo area at some point and renewed their friendship with Livingston.

After he finally moved back to Fort Pierce, Roberts painted in his backyard under a Brazilian pepper tree with a piece of red carpet underneath his sandaled feet. His garden of collard greens was nearby. He would often paint without a shirt in order to keep cool in the Florida heat. A shirtless portrait of him on the obelisk honoring the Highwaymen, in the center of the roundabout at 15th Street and Avenue D, commemorates his artistry. This image is also on the back cover of Bob Beatty’s 2005 book, Florida’s Highwaymen: Legendary Landscapes.

Sadly, it was some of the pleasures he enjoyed most that would contribute to his death. Livingston Roberts was a heavy smoker who often lit a cigarette while painting. The combination of paint fumes and cigarette smoke lead to lung cancer. Once he became sick, he became more reflective. He talked about returning to his place of birth by the St. Johns River to paint his early home. According to Gertrude Walker, he was raised a Baptist and had deep faith in God. He consistently paid tithes to the church, although he was not a parishioner during his adult years. As he aged, Livingston believed he was meant to be a minister. While this realization was not to be, he was at peace with God before he died. Mary Ann Carroll shared a prayer with him the day before he passed on January 17, 2004. She remembers that Livingston, even in his final days, enjoyed a good drink and a hearty laugh. Even when he was sick, she said, he was loving. While Livingston Roberts may not have become a minister, he is credited with many acts of good will.

At the time of his death, he was married to Cleo Roberts.  Together they had three sons, two daughters, five step-sons, and five step-daughters. James Gibson, who spoke a his memorial service, said, “Whenever I needed inspiration, I would go over to Castro’s backyard to watch him paint.”  Livingston is buried in Pine Grove Cemetery in Fort Pierce. In February 2005, his sister Gertrude commissioned Anita Prentice to create a mosaic re-creation of a Livingston Roberts landscape.  It was placed on his grave along with a bronze plaque, made by Pat Cochran, that states “I can feel the angels guiding my hands.” On the first anniversary of his passing, St. Lucie County History Museum had an exhibition of his work.

In the words of his sister, Gertrude Walker, “He was a charismatic teacher as much as an artist. His backyard was a gathering place for his fellow Highwaymen as well as people of all ages who came by to watch him paint. He had a great sense of humor and enjoyed telling stories, having a beer, a cigarette, and a good laugh. If anyone needed money and he had it to give, it was readily handed over.”

His Painting

Livingston Roberts liked to paint early in the morning when his mind was fresh, often at 2:00 a.m. He was more meticulous with his painting than other Highwaymen, and getting it right was important to him. He painted varied and detailed landscapes for 47 uninterrupted years. His drive to be an artist, as his sister Loretta Moran claimed, was born in him.

Bean Backus was a friend, and a strong influence on him. Livingston often visited Bean’s studio and learned from him in informal ways. His paintings are distinguished by his thickly layered paint. Unafraid of color, his skies were often brilliantly colored and his water’s reflections intense. He liked using light and shadow, and his images often evoked dawn and dusk when Florida’s skies are most dramatic. Inspiration for his work came mostly from memory, but he also studied images collected from magazines.

He signed his work “L. Roberts,” carefully painting each letter, unlike most of the Highwaymen who often used a palette knife to scratch their names into the wet paint.

Livingston Roberts paintings always sold well. He is considered to be one of the most important painters in the Highwaymen group and he was certainly one of the most influential. Al Black said of Livingston, “He was the best painter of all the Highwaymen, and the nicest. I have sold Castro’s paintings since 1963. From Key West to Montgomery, Alabama, you just show them and his paintings sell themselves.”