Midkiff was 26 years old when he made his Major League debut on October 5, 1909, with the Cincinnati Reds. After spending time in the minor leagues, Midkiff was acquired by the Highlanders from the San Antonio Bronchos of the Texas League in 1912. Midkiff spent 1913 as the starting third baseman for the Yankees, but Fritz Maisel took the job midway through the season, and Midkiff was sold to the minor league Baltimore Orioles in August.\n', '

In 1914, Midkiff was a teammate of Babe Ruth before Ruth came to the majors. After parts of two seasons in Baltimore, Midkiff ended the 1914 season with the Louisville Colonels of the American Association.\n', '

In May 1915, Midkiff was named the Colonels\' manager. Midkiff, who was at the time suffering from a broken ankle, was named Manager of the club in place of John F. Hayden. At the end of the season, Midkiff was let go, and signed with the Memphis Chickasaws of the Southern Association. He continued to play in the minor leagues until 1921, and as late as 1940 managed the Huntington Aces of the class-D Mountain State League.\n', '

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