The 1899 Kentucky gubernatorial election was held to choose the new governor of Kentucky, as the incumbent could not seek re-election. After a chaotic nominating convention, the Democratic Party chose William Goebel as their nominee, angering a faction of the party who then held their own convention and chose John Y. Brown as their nominee. The Republicans nominated William S. Taylor, despite the current governor's lack of support. Taylor won the general election by a small margin, but the results were challenged due to voter fraud. A committee was created to investigate, but before their report was issued, Goebel was shot and killed. Taylor was deposed and J.C.W. Beckham became governor. Taylor fled to Indiana and several people were charged with Goebel's murder, but the identity of the assassin remains unknown. In the 1895 gubernatorial election, the first Republican governor, William O. Bradley, won because of divisions within the Democratic Party and a strong third-party candidate. This election marked the start of two-party competition in Kentucky. William Goebel, a powerful Democrat, rose in power and sponsored the Goebel Election Law, which was seen as partisan and self-serving. The law was passed and upheld as constitutional by the Court of Appeals. In the Democratic nominating convention for the 1899 Kentucky gubernatorial election, three candidates - Goebel, Hardin, and Stone - were vying for the nomination. Hardin was initially favored to win, but Goebel and Stone formed an alliance to prevent that. The convention became chaotic and was filled with disruptions, but Goebel ultimately secured the nomination with the support of Stone's delegates. Hardin and Stone pledged their support to Goebel, but some did so reluctantly. The Republican nominating convention took place in Lexington, Kentucky on July 12. Governor Bradley did not attend as he was unhappy with the party's consideration of his candidate. There were threats of a black-led convention, but Taylor tried to keep the party together by promising to appoint black leaders to his cabinet if elected. Taylor's superior organization led to his unanimous nomination, as well as the nominations of John Marshall, Caleb Powers, and Judge Pratt for other positions. After being dissatisfied with the outcome of the Music Hall Convention, some Democrats called for a new convention led by U.S. Senator Jo Blackburn's supporters. Former governor John Y. Brown caused a stir by announcing he would accept the nomination from this new convention. The convention, attended by representatives from 108 of Kentucky's counties, nominated an entire slate of candidates and condemned the Music Hall Convention, the Goebel Election Law, and President William McKinley's administration.

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