Isaac was born on a 100 acre farm outside of Tallahassee where his family grew cotton, peanuts, sugarcane, and various kinds of vegetables, especially okra. One of the younger children of six, he worked the fields at an early age. His watched his father labor around the clock. Besides farming, he made moonshine, which brought in some extra money.
Attending school was challenging. Isaac had to walk over 5 miles each way. Once a school bus became available, he still had to walk a mile to the bus stop. He only attended 3 or 4 days a week and consequently did not excel in school. His mother died when he was young and his father remarried a woman who was years younger than his father. She was a hot-tempered drinker, and because of her, life at the Knight home became extremely difficult. Isaac dropped out of school in the 11th grade. At the age of 17 he left his family’s troubles behind and focused on doing something besides farming. He settled in Fort Pierce where he had family.
Knight found work in a hospital and later with the state road department. But he wasn’t content with these jobs and knew he had to do better. He kept looking for opportunities until he found a job at Northrop Grumman Aerospace where he worked fulltime for 31 years. He retired in 1994.
Isaac jokes that his wife Lillie tricked him into marrying her. She worked in a store and would watch him walk by. Although he didn’t smoke, he figured he’d start a conversation with her by asking what kind of cigarettes he should purchase. She said she didn’t smoke but thought a pack of Kent cigarettes might be good. The relationship moved quickly from there. In one month they were engaged; three months after they met they were married. They have now been married over 50 years. The couple has two children. Their son Cedric is a successful businessman living in the Orlando area and their daughter Tiffany, who has a disability, lives in Vero Beach. Isaac and Lillie are raising Tiffany’s daughter Desirae, who refers to Isaac as “Dad.”
Lillie’s sister was married to Highwayman Al Black, making Isaac and Al brothers-in-law. Being family, Al enlisted Isaac’s help in selling paintings by Alfred Hair and some of the other landscape artists. Isaac obliged, selling on Saturdays and sometimes on Sundays. The first Saturday they went out together, Al told Isaac to just observe. By 1:00 in the afternoon, all the paintings had been sold. “Al always sold out,” Isaac explains. “We got $40 to $50 for a painting back then and that was a lot of money.”
Selling on the road provided Isaac with some good stories. One time when Al and Isaac had just finished selling all their paintings in Orlando and were heading home, Al saw a sign for a dog track. He stopped and gambled all their day’s earnings, losing everything. They didn’t want to face Alfred with the truth, so Al told him that they had sold all the paintings to one person who was going to pay them the next day. They said they trusted the buyer and had allowed him to keep the paintings. They then took the next day’s stack of paintings and sold them all at good prices. Alfred was satisfied with the money that came in and he never suspected anything. For Isaac, this experience was a bit scary. “I’ve never been a gambler,” he explains, “but Al, he gets carried away.”
There were other things that Isaac and Al kept from Alfred. Always looking to make more money, Al realized that they should start making their own paintings. So they got some art supplies and created their own landscapes, building off of what they had seen others do. Keeping their painting activities secret, they included their own work in the batch they were selling for other painters. Later, they purchased art supplies from Bean Backus who gave them tips on how to paint. Isaac sold his first painting for $20. As far as Isaac knew, Alfred never found out two of his best sellers were also painting.
In the early days, painting, for Knight, was a way to earn extra money. He wanted to be more successful than his fulltime job would allow and the weekend work really helped with finances. When he came home with a pocket full of money, he jokes that “Lillie would take it all.” And then she’d tell him he had done a good job and suggest he go out on the road again very soon.
Painting and selling their work was also a way that “helped break the color barrier,” explains Knight. It felt great to be a part of that movement, but once they were known as the Highwaymen and began receiving invitations to exhibit in major museums, “that was really exciting,” he explains.
Some years ago, his son Cedric suggested his father try painting a landscape in black, white, and shades of gray. He had a friend who was a black and white photographer and Cedric loved looking at the varying tones of his work. Isaac gave it a try. Now, rendering black and white landscapes is his signature style, although he’s always ready to paint a brightly colored scene as well.
Knight’s relationship to his family members is strong. He is a loving husband, father, and grandfather. Pictures of his family fill his house, especially of Desirae, who Isaac is teaching to cook as well as paint. His relationship with Lillie is evident to everyone who knows the couple. They had a huge celebration of their marriage on their fiftieth anniversary at their church. The large stack of celebratory cards contained money and gift cards equaling $3,000.
Isaac also cared for his father until he died. After a violent episode took place between his father and his stepmother, ending in his father’s incarceration, Isaac and Lillie stood by him. When he was released from jail in Tallahassee, they took him home to live with their family in Fort Pierce to keep him safe.
The house they live in was a gift from Lillie’s family when they got married. They are well rooted in this house, their neighborhood, and their community. Over the years, a number of Highwaymen have come to the Knight’s house to paint. Isaac explains that the friendships have remained strong but that they can still be competitive.
Life is very different for Isaac these days. He goes to dialysis three days a week as he waits for a kidney transplant. Still, he takes pleasure in each day. He raises a few vegetables in his home garden and he and Lillie go to art shows together. He paints in his garage whenever he can, and he and Lillie are working on a book about Isaac’s Highwaymen adventures.
He paints in his garage where he sets up more than one canvas at a time. Most of his scenes come from his memory. Even in the early days, he never painted from pictures; instead, he remembered the landscape from his travels around the state. He continues to experiment with his signature black and white landscapes and still makes about half his own frames.
Isaac strongly believes in sharing what he has learned. He teaches at a school in Stuart several times a year, as well as at Desirae’s school and his church. If the Highwaymen tradition carries on to other generations, that would make Isaac Knight a happy man.