"Happy" Jack Chesbro

John Dwight Chesbro was born in North Adams on June 5, 1874 and grew up at 177 Bracewell Avenue. His personality was such that he was dubbed “Happy Jack” at an early age. As he matured his interests turned to the game of baseball, specifically the position of pitcher. He played on most any team that would have him here in Berkshire County as well as teams in an around the Springfield area.

In 1894 he answered a posting in the newspaper to work at a Massachusetts mental hospital which also fielded a baseball team. The following year, he moved to the Albany area, pitching for Johnston in the New York League. Unfortunately, that didn’t last long because the league folded due to lack of money. By 1896, Jack was playing semi-pro ball in Cooperstown, NY. 

A year later, the 5 foot 8 inch, 180 pound Chesbro was playing in the Atlantic League. It was there that the major league ball clubs began to show an interest in Happy Jack. He came very close to signing with Baltimore until the Orioles backed off without a known reason. His disappointment didn’t last long however when the Pittsburg Pirates came knocking on his door. He signed a $1,500 contract and, to show Baltimore they made a mistake, Jack won 17 games and lost only 4.

Chesbro, backed up by Honus Wagner and other great players, helped Pittsburg move from 7th place, in 1899, to the National League Pennant in 1901. He led the league with 21 victories and 10 loses. In 1902 Jack perfected the spitball, then a legal pitch. That year he won 28 games and lost only 6. Changes would come to Chesbro in 1903. 

In 1903, the American League was formed to counter the dominance of the National League.

Happy Jack took his spitball to play for the New York Highlanders (later the New York Yankees). He pitched in their very first home game, beating the Washington Senators 6-2. The Highlanders ended the season in 4th place. This only made Jack more determined to win the following season.

In 1904, he won 41 games and lost 12 (a winning record that stands to this day), gave up 338 hits, 88 walks and struck out 239. His earned run average was 1.82. Despite these stats, the Highlanders lost the pennant on the last day when Chesbro throw a wild pitch. It was said to be his greatest disappointment. 

His last season in the majors was in 1909 when he was released by the New York team and signed by the Boston Red Sox. He only needed eight more wins to reach 400 games, but that was not meant to be. Jack only pitched in one game for the Boston team, which he lost to New York.

When he retired from baseball, he moved to Conway, MA and bought a farm to raise chickens. He kept his hand in baseball however by coaching the Amherst College baseball team. In 1924, he accepted a coaching job with the Washing Senators. Because of failing health, Jack left the team moved back to Conway. In 1931 he suffered a heart attack and passed away on November 6, 1931 and was buried in Howland Cemetery in Conway.