Killefer made his major league debut at the age of 21 with the St. Louis Browns on September 13, 1909. After the 1910 season in which the Browns finished in last place, Killefer was released to the Buffalo Bisons of the Eastern League. Under the tutelage of Bisons\' manager George Stallings, Killefer developed into a refined catcher.\n', '

His contract was purchased by the Philadelphia Phillies on August 19, 1911, and he played his first game as a starter on October 3. The Phillies pitcher on that day was Grover Cleveland Alexander, and the game marked the first of 250 times the pair teamed up as a battery in the major leagues. Although he was a light hitter, Killefer became known for his strong defensive skills. In 1913, he led National League catchers with 166 assists, 130 baserunners caught stealing, a 50.6% caught stealing percentage, and finished second in putouts and fielding percentage.\n', '

In 1914, Killefer made news when it was reported that he had signed with the Chicago Whales of the Federal League, although he denied the report. When the Phillies offered him a salary increase, he decided to sign with the Phillies, which led the Federal League to file a lawsuit against him and the Phillies. A judge ruled against the Federal League and Killefer remained with the Phillies.\n', '

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