A multi-sport athlete during his college days at Transylvania College, Chandler briefly considered a career in professional baseball before deciding to pursue a law degree. After graduation, he entered politics and was elected as a Democrat to the Kentucky Senate in 1928. Two years later, he was elected lieutenant governor, serving under Governor Ruby Laffoon. Chandler and Laffoon disagreed on the issue of instituting a state sales tax and when Chandler, the presiding officer in the state senate, worked to block the legislation, Laffoon's allies in the General Assembly stripped him of many of his statutory powers. The tax then passed by a narrow margin. Knowing that Laffoon would try to select his own successor at the Democratic nominating convention, Chandler waited until Laffoon left the state—leaving Chandler as acting governor—and called the legislature into session to enact a mandatory primary election bill. The bill passed, and in the ensuing primary, Chandler defeated Laffoon's choice, Thomas Rhea. He then went on to defeat Republican King Swope by the largest margin of victory for a Kentucky gubernatorial race at that time. As governor, Chandler oversaw the repeal of the sales tax, replacing the lost revenue with new excise taxes and the state's first income tax. He also enacted a major reorganization of state government, realizing significant savings for the state. He used these savings to pay off the state debt and improve the state's education and transportation systems.