On May 25, 1913, after giving the starting shortstop position to Ray Chapman, the Naps traded Peckinpaugh to the New York Yankees for Jack Lelivelt and Bill Stumpf. The Naps soon regretted the trade. With the Yankees, Peckinpaugh emerged as a team leader. He was named captain in 1914 by manager Frank Chance. Chance resigned with three weeks remaining in the season, and Peckinpaugh served as player–manager for the remainder of the season; at the age of 23, he became the youngest manager in MLB history. He finished the 1914 season fifth in the AL with 38 stolen bases. Bill Donovan was hired as the Yankees manager in the offseason. In the 1914–15 offseason, Peckinpaugh considered leaving the Yankees to join the Federal League, as he received offers from the Chicago Federals, Buffalo Blues, and Indianapolis Hoosiers. After considering the offer from Chicago, he chose to stay with the Yankees, and received a three-year contract worth $6,000 ($ in current dollar terms) per season from 1915 through 1917. He resigned with the Yankees in 1918. Peckinpaugh tied Buck Weaver for fourth in runs scored (89) and several players for eighth in home runs (7) in the 1919 season. By the 1921 season, Peckinpaugh was one of three players, along with Wally Pipp and Bob Shawkey, remaining with the Yankees from the time Jacob Ruppert and Tillinghast L'Hommedieu Huston purchased the team in 1915. The Yankees reached the World Series in 1921, losing to the New York Giants. Peckinpaugh set an MLB record for most assists in one game by a shortstop with nine. Washington Senators and Chicago White Sox (1922–1926) Peckinpaugh was traded twice during the 1921–22 offseason. On December 20, 1921, the Yankees traded Peckinpaugh with Rip Collins, Bill Piercy, Jack Quinn and $100,000 ($ in current dollar terms) to the Boston Red Sox for Bullet Joe Bush, Sad Sam Jones and Everett Scott. On January 10, 1922, Pecknipaugh was involved in a three-team trade involving the Red Sox, Washington Senators and Philadelphia Athletics, where Peckinpaugh joined the Senators, Joe Dugan and Frank O'Rourke went to the Red Sox, and the Athletics acquired Bing Miller, José Acosta, and $50,000 ($ in current dollar terms). Though team owner Clark Griffith had indicated that Peckinpaugh would serve as his player-manager at the time of the trade, he named Clyde Milan player-manager for the 1922 season instead. This distracted Peckinpaugh, and along