Following his term as commissioner, Chandler returned to Kentucky and won a second term as governor in 1955. The major accomplishments of his second term were enforcing the racial integration of the state's public schools and establishing a medical school at the University of Kentucky which was later named the Chandler Medical Center in his honor. Following his second term as governor, his political influence began to wane as he made three more unsuccessful runs for governor in 1963, 1967, and 1971. His endorsement of dark-horse candidate Wallace G. Wilkinson was seen as critical to Wilkinson's successful gubernatorial campaign in 1987. Wilkinson later resisted calls to remove Chandler from the University of Kentucky board of trustees following Chandler's use of a racial epithet during a board meeting in 1988. In his retirement, Chandler made numerous public appearances and remained active in state politics and events. Chandler died a month before his ninety-third birthday; at the time, he was the oldest living former Kentucky governor as well as the earliest serving former governor.