 McCreary campaigned for Democrat William Goebel during the controversial 1899 gubernatorial campaign. Between 1900 and 1912, he represented Kentucky at four consecutive Democratic National Conventions. Governor J. C. W. Beckham and his well-established political machine supported McCreary's nomination to the Senate in 1902. His opponent, incumbent William J. Deboe, had been elected as a compromise candidate six years earlier, becoming Kentucky's first-ever Republican senator. Deboe had done little to secure support from legislators since his election, however, and McCreary was easily elected by a vote of 95 – 30. Following his election to the Senate, McCreary supported Beckham's gubernatorial re-election bid in 1903. In a largely undistinguished term as a senator, he continued to advocate the free coinage of silver and tried to advance the state's agricultural interests.
