On April 25, 1904, New York Highlanders pitcher Jack Chesbro recorded his first victory of the season. The Highlanders played their games at Hilltop Park, which was located in Washington Heights. If you are a regular reader of this column, you might know that the Highlanders would eventually become the New York Yankees.
Many of today’s fans might not know the name of Jack Chesbro, and even fewer know that the New York ace owns an MLB record that will never be broken.
We all know baseball fans. Next time, you see one, ask them which records they think will never be broken. “DiMaggio’s 56-game hitting streak” is a usual first reply. “Cy Young’s 511 wins” is another popular response. When one responds, “Jack Chesbro’s 41 wins in a season”, the all-too-familiar refrain of “Who?” always follows.
Hence, the reason for this story, and quite honestly, one of the inspirations for Gotham Baseball.
“Only the die-hard baseball fans know about Chesbro”, said former Baseball America’s Executive Editor Jim Callis. “To many, his achievements were attained too long ago, and they have faded in memory.
“He shouldn’t be anonymous.”

John D. “Jack,” also known as “Happy Jack” Chesbro, was born on June 5, 1874, in North Adams, Massachusetts. As a boy, he learned how to play the game of baseball with teams like the Houghtonville Nine and other sandlot teams in the locale.
He joined the majors in 1899, as the Pittsburgh Pirates paid the then-princely sum of $1,500 to acquire his services. It would take until 1901 for that initial investment to pay off, as Chesbro enjoyed his first 20-win season (21-10, 2.37 ERA), leading the Pirates to their first-ever NL pennant in 1901.
Chesbro followed that year up with an even better season in 1902, posting a 28-6 record with a 2.17 ERA, the year in which he is believed to have first started throwing the spitball.
Seeking to make the most money he could, Chesbro jumped to then-manager Clark Griffith’s Highlanders for their first AL season in 1903, going 21-15 with a 2.77 ERA.
He pitched the very first game for the Highlanders (now the Yankees) in team history – a loss – but he became the first ace of New York’s AL squad. With three straight 20-plus win seasons – and an unhittable pitch – under his belt, Chesbro would put together the best single-season by any starting pitcher in major league history in 1904.
He started 51 games, completed 48, and tossed 454 innings. He threw six shutouts, walked just 88 batters, and posted a brilliant 41-12 record with a 1.82 ERA. However, it is the last game he pitched in that season, quite unfortunately, that he’s best remembered for.
All during the 1904 season, the Highlanders were part of a five-way fight for the pennant with the Red Sox, White Sox, Indians, and Philadelphia A’s, and it was decided with a five-game series between New York and Boston that ended the season.
The Highlanders won the first game, taking a half-game lead. Boston swept a doubleheader the following day and went ahead by a game and a half, leaving a doubleheader the Highlanders had to sweep to overtake Boston.
The Highlanders won the first game, but in the ninth inning of the second game, Chesbro’s spitter sailed over the catcher’s head and gave the Red Sox the pennant. The bitter defeat overshadowed Chesbro’s brilliant season, and though he went 19-13 with a 2.20 ERA in 1905 and a 24-16 record with a 2.96 ERA in 1906, the specter of that wild pitch stayed with him until he left baseball.
He was 10-10 in 1907, 14-20 in 1908, and New York released him during the 1909 season. He finished his career by pitching one game, a loss, for the Boston Red Sox later that season. In 1911, Chesbro coached baseball at Amherst College in Massachusetts, briefly returned to the majors to coach for the Washington Senators in 1924, and passed away on November 6, 1931.
Seventeen years after his death, he was elected to the Hall of Fame in 1946, and he is the only player among the Cooperstown greats who pitched for a Cooperstown team, the semi-pro Cooperstown Athletics in 1896.
Of all the players enshrined in the Hall of Fame who have worn a New York uniform, he is easily the least known and least appreciated. However, when all is said and done, his 41 wins in a single season remain unbreakable.