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In the 1959 gubernatorial primary, Chandler threw his support to Lieutenant Governor Harry Lee Waterfield.
The anti-Chandler forces eventually put forth Bert Combs as their nominee again.
Having learned from his previous campaign, Combs now attacked Chandler for allegedly requiring state employees to donate 2 % of their salaries to his campaign.
According to Combs, Chandler had deposited the money in a Cuban bank, but the money was lost when Fidel Castro overthrew the government in the Cuban Revolution.
Ultimately, Combs prevailed in the primary by a vote of 292, 462 to 259, 461.
Republicans nominated John M. Robsion, Jr. to oppose Combs, and when Democratic President Harry S. Truman came to Paducah to campaign for Combs, Chandler refused to welcome him to the state, a customary duty of the sitting governor.
Instead, in a letter to Truman, Chandler launched a blistering attack on his party's nominees, calling Combs a liar and alleging that his running mate, Wilson W. Wyatt, who had previously served in Truman's administration, had actually tried to undermine Truman by helping found Americans for Democratic Action.
Combs ultimately won the general election by a wide margin.

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