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Isaac was born on a 100 acre farm outside of Tallahassee where his family grew cotton, peanuts, sugarcane, okra and other vegetables. Isaac worked the fields at an early age. He began his journey as a Highwayman by selling other artists’ work. He started painting when he realized he could make more money if he sold and painted. Painting and selling was a second job for Issac so he worked at it on weekends and during the evenings.

At the age of 17 Isaac left his family’s troubles behind and focused on doing something besides farming. He settled in Fort Pierce where he had family. Knight worked various jobs before finally finding a job at Northrop Grumman Aerospace where he worked full time for 31 years. He retired in 1994.


In the early days, painting, for Knight, was a way to earn extra money. He wanted to be more successful than his full time job would allow, and the weekend work really helped with finances. One weekend when he came home with a pocket full of money, he joked that “Lillie (his wife) 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. 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.

Knight’s career didn’t truly begin until after the fame earned in the late 1990’s. His earlier paintings are less common, but he created thousands of paintings over the last 20 years. He painted until his passing in 2022, but his style is still true to the group; creating classic yet simple Florida landscapes at affordable prices.

Biographies are adapted from those on, one of the earliest informative websites on the Florida Highwaymen. Since the site is no longer active, we have provided them here.

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