Chesbro's major league debut came with the Pittsburgh Pirates in 1899. During his time with the Pirates, he quickly established himself as a reliable pitcher. His performance in the 1902 season was particularly impressive, as he helped lead the Pirates to a National League pennant with a 28-6 record and a 2.17 ERA. This season marked the beginning of Chesbro's rise in the baseball world.
In 1903, Chesbro joined the New York Highlanders, a team that would later become the New York Yankees. It was with the Highlanders that Chesbro achieved one of the most remarkable feats in baseball history. The 1904 season saw Chesbro pitch an astounding 454.2 innings, winning 41 gamesโa record that still stands as the most wins in a single season in the modern era. His 41-12 record and 1.82 ERA that year were instrumental in the Highlanders' strong performance, although they narrowly missed winning the American League pennant.
Chesbro's pitching style was characterized by his use of the spitball, a legal pitch at the time, which added an unpredictable movement to his throws. This, combined with his stamina and control, made him a formidable opponent on the mound. His ability to pitch complete games was a testament to his endurance and skill, as he often carried his team through long stretches of the season.
Despite his success in 1904, Chesbro's subsequent seasons were less dominant. He continued to pitch for the Highlanders until 1909, but his performance gradually declined, partly due to the heavy workload he had shouldered in previous years. Nevertheless, he remained a respected figure in the league, known for his competitive spirit and dedication to the game.
After retiring from professional baseball, Chesbro returned to Massachusetts, where he lived until his passing on November 6, 1931.
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