Jack Chesbro didn’t make the majors until age 25. He only lasted 11 seasons, and two of them were partial years, but he was still able to parlay some early success with the Pirates and one magical season with the Highlanders into a Hall of Fame career. 
Back in 1895 Chesbro was beginning his minor league career in Springfield, Massachusetts, not far from his hometown of North Adams. He went 2-1 but was very wild and hittable. He also played for two minor league teams in New York that year. The next season he found a regular job in Roanoke, Va and pitched better despite his 8-11 record, which was mostly due to some poor fielding that led to a ton of unearned runs.
By 1897 he found himself in Richmond where played for three seasons before ever getting his first chance in the major leagues, despite some good stats including a 17-4 record his final season. His chance at the majors finally came when the Pittsburgh Pirates came calling in July of 1899. Chesbro would make his big league debut on July 12th of that year as a starter in New York vs the Giants where he would lose 4-1. Just two days later he would take his 2nd career loss, this one 2-0 near his hometown vs the Boston Beaneaters (current day Atlanta Braves). He finally got his first win on July 18th vs Brooklyn by a score of 8-2 which made it three straight road starts to open his Pirates career.
Chesbro finished his rookie campaign with a 6-9 4.11 record. He was a regular in the rotation until mid-September but he missed the last month of the season. Despite an odd 59/28 BB/K rate the Pirates liked what they saw from him. He was part of the December 1899 deal that brought Honus Wagner and half of the Louisville team to Pittsburgh, but that was just a paper deal as Louisville was about to fold and their owners were actually also part owners of the Pirates. Chesbro was returned to Pittsburgh on March 9, 1900 and he would be a regular in their rotation that season.
In 1900 the Pirates were much better and so was Chesbro who was only the 5th best pitcher on the team. Future Hall of Famer Rube Waddell along with star pitchers Sam Leever, Deacon Phillippe and Jesse Tannehill all had ERA’s under 3.00 while Chesbro was still respectable with his 15-13 3.67 record. He still had trouble with the walks and wasn’t much of a strikeout pitcher but better years were ahead for the 26 year old and the Pirates.
In 1901, the team was an obvious contender for the NL title and for the first time in their history they would win the National League crown and rather easily too. They went 90-49 to finish 7.5 games ahead of the Philadelphia Phillies. The team was without Waddell almost the entire season but the other four stepped up to go a combined 75-37 with Chesbro going 21-10 2.38 and leading the league in shutouts with six. His contract actually had a bonus in it for $100 if he won more than half of his starts and his salary for that 21 win season before that bonus was just $1,900.
The Pirates team was then considered a powerhouse and Chesbro was among the elite pitchers in the league. His 1902 season was one of the best in Pirates history and the 1902 Pittsburgh team absolutely dominated the NL going 103-36, an unbelievable 27.5 games ahead of the 2nd place Brooklyn Superbas (current day Dodgers). Jack finished the season 28-6 2.17 with eight shutouts. His win total, winning % and shutouts all led the NL. His win total is also the highest mark for any Pirates pitcher since 1896 and his shutout total is tied for the highest since the Pirates moved to the NL, topped only by Cannonball Ed Morris, who had 12 in 1886 while the franchise was in the American Association.
Despite the success the team had, and what he was able to accomplish with them, Jack and four of his Pittsburgh teammates had decided to jump to the newly formed American League. Back then it was more common but hard to imagine in this day and age, the five of them had actually signed contracts for 1903 with the New York Highlanders during the 1902 season while still with the Pirates. Chesbro had received a raise all the way to $5,000 so the jump was worthwhile to him but the AL team definitely got their money’s worth from him.
Jack Chesbro is remembered for two things among most who study the game. In 1904 he won what is considered the modern day record of victories in a season with 41. That fact is always followed by the fact he lost the pennant with a 9th inning wild pitch allowing the winning run to score as the Highlanders lost to the Boston Americans 3-2. The were playing a doubleheader and with a sweep the Highlanders would’ve won the title. For a season in which he went 41-12 and had completed 48 of his 51 starts, all that people remembered on that last day was his wild pitch.
He would last until 1909 with the Highlanders posting a 66-66 record the rest of the way with them and he never made the playoffs. The Pirates of course made two World Series appearances during that time and won the 1909 championship. In one last hurrah to his career he signed with his hometown Boston Red Sox team and on the last day of the season they let him start game one of a doubleheader vs his former team, the Highlanders. He would lose 6-5 and retire following that game.
With the Pirates he finished 70-38 2.89 and in his career he had a 198-132 2.68 record. He died in 1931 and never garnered much support for the Hall of Fame until 1946 when an Old-Timers Committee elected a group of players with mostly marginal cases for the HOF. Among them was Chesbro who was no better than many pitchers of his day including long-time Pirates Sam Leever and Deacon Phillippe who both had better lifetime ERA’s and winning percentages than Chesbro. His election was likely based on poor record keeping up to that day and the fact he won 41 games in one season. Had he gone 21-6 over two seasons instead of 41-12 in one year he likely wouldn’t be a Hall of Famer to this day.
