Career
He played for the Saint Louis Browns, Pittsburgh Pirates, and Chicago Cubs. In 1905, Leifield was the ace of the Western League"s Des Moines Underwriters, winning 26 games to help the Underwriters take the pennant. In September, Pittsburgh Pirates owner Barney Dreyfuss purchased his contract for $2,500.
Leifield pitched a shutout in his major league debut.
From 1906 to 1911, Leifield stayed in the Pittsburgh starting rotation, winning 15 or more games each season. He was traded to the Chicago Cubs in 1912.
After being released in 1913, Leifield returned home, and then went to San Francisco, California to pitch in the Pacific Coast League. In 1915, he went to spring training with the Pirates but instead played for the Saint Paul Saints of the American Association.
On August 20, he struck out 15 in a game for the Saints.
In 1918, Leifield returned to the majors as a player-coach for the Saint Louis Browns, and then as a full-time coach for the Boston Red Sox and Detroit Tigers. He finished his major league career with 124 wins. Leifield died in Fairfax, Virginia at the age of 87.