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The earliest Yankee pitcher in the Hall is Jack Chesbro. Poached from the Pirates when the Highlanders began play in 1903, Chesbro pitched for the club during their first six seasons of existence. He led the AL with 41 wins, 48 complete games, and 454.2 IP in 1904, but notoriously uncorked a ninth inning wild pitch on the season's final day, costing the Highlanders the back end of a double header against the Boston Pilgrims and handing the pennant to their future arch rivals by a game and a half.
Waite Hoyt and Herb Pennock led the pitching staff through the 1920s, as the team won their first pennants and World Series titles. But both were acquired from other organizations, as was Red Ruffing, a Hall of Famer himself, who joined the club in 1930. For the next thirteen years Ruffing would team the Yankees first homegrown ace to lead the team to seven pennants and six World Series championships.
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He made his Major League debut early in the 1930 season but also spent part of the year at the Yankees' AA affiliate in St. Paul. His Major League line wasn't pretty, just 2-5 with 5.55 ERA over 60 innings, most of them coming in relief. Gomez rebounded in a big way for his sophomore campaign, becoming the staff ace and leading the club in IP, wins, strikeouts, and ERA. His ERA slipped slightly below league average the following year, but he still led the club in wins and ERA, and finished fifth in MVP voting as the Yankees won their first World Series in four years. In post season play for the first time in his career, Gomez went the distance in Game Two of the Series, allowing just ten baserunners and a lone earned run on the way to a sweep of the Cubs.
Lefty turned in another solid campaign in 1933, again leading the Yankees in wins and ERA, falling just a third of an inning shy of tying Ruffing for the club lead, and leading the AL in strikeouts for the first of three times in his career. He followed that with the best season he would ever have. He led the American League in wins, winning percentage, ERA, ERA+, complete games, shutouts, strikeouts, and WHIP, earning him a third place finish in the MVP voting.
Gomez' record slipped below .500 in 1935, but his peripheral numbers were still excellent as he and Ruffing again fronted the pitching staff. The two would combine to carry the staff to an unprecedented four straight World Series titles from 1936-1939. Gomez went 64-38 (.627) over that stretch, with a 138 ERA+. He led the league in wins, ERA, and strikeouts in '37, marking the second pitching Triple Crown of his career. He also led the League in shutouts in '37 and '38. He won five World Series games over that run, leaving him with 6-0 record and 2,86 ERA in seven starts in the Fall Classic.
Gomez began to fade a bit towards the end of that historic run, falling just under 200 IP for the first time in his career in 1939. He was limited to just nine games in 1940, but rebounded pitch on pennant winners in 1941 and '42. He didn't see any action in those World Series, and was sold to the Braves in early 1943. Gomez never appeared for them, landed in Washington for one last start, and called it a career.
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Always a quick thinker and quipster during his playing career, Gomez became a favorite on the off-season banquet circuit after his retirement. He remained in the Yankees organization as a manager, skippering the AA Binghamton squad in the late forties. Whitey Ford would go on to replace Gomez and Ruffing as the best pitcher in franchise history. Both Gomez and Ford were honored with plaques in Monument Park in August 1987. Ruffing would join them there in 2004. Gomez was unanimously elected to the Hall of Fame by the Veterans Committee in 1972, five years after Ruffing and two years before Ford.