Chester-Burton was elected as the first African American to serve on the Shively City Council. During her 10 years in the City Council, Chester-Burton was dedicated to changing the past perceptions of Shively after she lost her first mayoral campaign in 2008. In 2018, she broke down a major barrier in a city known for its racist past by being elected as the first African-American to lead Shively in its 80-year history. With Chester-Burton being elected with 97.8% of the vote, her election created a new legacy.

Chester-Burton is also a teacher in Jefferson County Public Schools and an equity and inclusion facilitator for the National Education Association. Chester-Burton is a role model for many people in Shively, including her daughter, Tiffany Burton. Tiffany watched her mom walk through different political positions, which eventually motivated her to follow in her mother's footsteps by running and winning a position on Shively City Council. Her civic, community involvements, and recognitions are numerous.