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Pinstripe Alley Top 100 Yankees: #44 Jack Chesbro

Chesbro authored one of the all-time best single seasons in Yankees history and was the franchise’s first ever star.

Jack Chesbro Rose Postcard Photo Reproduction by Transcendental Graphics/Getty Images

Name: John Dwight “Jack” Chesbro
Position: Starting pitcher
Born: June 5, 1874 (North Adams, MA)
Died: November 6, 1931 (Conway, MA)
Yankee Years: 1903-09
Primary Number: N/A
Yankee Statistics: 269 G, 227 GS, 1952.0 IP, 2.58 ERA, 109 ERA+, 1.120 WHIP, 913 K, 29.8 bWAR, 30.2 fWAR


The Yankees’ franchise existed long before they started winning World Series titles. Exactly 20 years before Babe Ruth and company won the 1923 championship, the New York AL franchise then known as the Highlanders began play. While so much of that time is lost to history, there were some great players prior to 1923. One of them was Jack Chesbro, who put in a season for the ages in 1904.

The Early Life and Career of “Happy Jack”

Born to Chad and Martha, Chesbro grew up in Massachusetts, the fourth of five children. Growing up, the family name was actually spelled “Cheesbro” and was pronounced the amusing way it appears on paper, but by the time Jack started making his name on the baseball diamond, he spelled it Chesbro and pronounced it “Chez-bro.”

Having impressed while playing for local amateur teams in Massachusetts, Chesbro was picked up by a team in Middletown, New York in 1894. The team was known as the “Asylums” because, well, they represented the local mental hospital. While playing for the team, he worked in the hospital and got his “Happy Jack” nickname thanks to his generally cheery attitude.

Besides that, Chesbro also starred on the mound for the Asylums, and would soon get picked up by Albany of the New York State League for 1895. While that team, and the league itself folded before the season finished — which would become a weird theme early in Chesbro’s career — the pitcher impressed enough to get signed by the Springfield Maroons of the Eastern League.

Springfield apparently didn’t like what they saw and released Chesbro after just a handful of games. The next year, he was acquired by the Roanoke Magicians of the Virginia League for 1896, but again the team folded before the season came to an end. Despite that, he did well enough there to get picked up by the Richmond Giants of the Atlantic League in 1897. After a couple seasons there, he really started to impress in 1899, going 17-4, and catching the eye of the Pittsburgh Pirates.

In July 1899, the Pirates purchased Chesbro from Richmond and gave him his major league debut later that season. However, he struggled that season putting up a 4.11 ERA (93 ERA+) in 149 innings as the Pirates finished near the bottom of the NL.

Chesbro with the 1900 Pirates (top row, second from right)
Public domain/WikiCommons

After the season, he was included in a 16-player trade that brought Honus Wagner and others to the Pirates and sent Chesbro and a couple others to the Louisville Colonels. However, Chesbro would never see the field in Louisville, as the team dissolved just a couple months after the deal. The former Louisville players would be assigned out through the NL and Chesbro ended up right back in Pittsburgh.


Chesbro apparently wasn’t happy to be right back with the team that had gotten rid of him, as he didn’t report to the team for spring training ahead of the 1900 season. However, he would eventually join the team and would improve on his previous season and spent the season as a regular member of the rotation, helping the Pirates jump up to second in the NL.

In 1901, Chesbro truly began to find his feet in the big leagues. He went 21-10 with a 2.38 ERA (137 ERA+), while also leading the NL with six shutouts. Along with a strong rotation and an excellent season from Wagner, the Pirates broke through and won the NL, 7.5 games ahead of the Phillies.

The next year, Chesbro continued his ascent as his 28-6 record would lead the league in both wins and pitcher winning percentage. He threw another eight shutouts as he again helped the Pirates to an NL pennant. With a 103-36 record, the Pirates were dominant in 1902, finishing 27.5 games ahead of second.

However, near the end of that season, reports began to emerge that Chesbro had agreed to jumped to the American League’s newly formed New York franchise for 1903. Due to those developments, he wasn’t allowed to participate in the Pirates’ postseason events (which did not yet include the World Series). After the squabbling leagues eventually came to a peace agreement, Chesbro was declared a member of the New York Highlanders for 1903 and beyond.

Jack Chesbro Warming Up

In his first season in New York, Chesbro was solid as the team’s ace pitcher. In 324.2 innings, he posted a 2.77 ERA (112 ERA+), while going 21-15, helping the Highlanders finish fourth in their first ever season. However, his marquee year was still yet to come.

A Legendary 1904 Season

In spring training 1904, the Highlanders played a series against a minor league team. In one of those games, future major league pitcher Elmer Stricklett faced off against New York’s lineup. Stricklett is credited as one of the fathers of the spitball, and Chesbro became fascinated watching him that day against his teammates, and set out to try and master it.

Despite his experimenting, Early on in the 1904 season, Chesbro didn’t use the spitball as both manager Clark Griffith and catcher Deacon McGuire were both against it. However, both the team and the pitcher got off to a middling start, culminating in Chesbro allowing seven runs on 13 hits in a loss to Cleveland on May 12th. After that loss, McGuire relented and agreed to catch the spitball. From there, both Chesbro and the Highlanders were off to the races.

Directly after he began implementing the spitball, Chesbro reeled off 14 consecutive wins, putting up a 1.40 ERA in 129 innings, holding hitters to just a .463 OPS. As well as the spitball, Chesbro also introduced and especially effective “slowball” as he put up cartoonish numbers in 1904.

Chesbro would set several Yankees single season franchise records in 1904 that will almost certainly never be broken. He appeared in 55 games, 51 of which were starts, throwing an insane 454.2 innings. He went 41-12, throwing 48 complete games, with a 1.82 ERA (148 ERA+), helping the Yankees finish second in the AL. Unfortunately for him, Chesbro was also part of the reason that second-place finish wasn’t a first-place one.

Late in the season, the Highlanders were locked in a pennant battle with the Boston Americans — later known as the Red Sox. They were set to take on Boston for five games, with just 0.5 separating them in the standings. Chesbro started the first of the five games on October 7th, throwing a complete game in a 3-2 win to allow the Highlanders to take over the lead.

Jack Chesbro Of NY Highlanders Photo by Chicago Sun-Times/Chicago Daily News collection/Chicago History Museum/Getty Images

While the series was supposed to be in New York, the middle two games had to be held in Boston on October 8th after Highlanders’ ownership had agreed to rent out their stadium for a Columbia University college football game. While it’s impossible to know what would’ve happened had the games been played in New York, playing them on the road was not kind to the Highlanders. They dropped both, falling 1.5 games back of Boston, meaning they would need to win both games of an October 10th doubleheader back in New York to win the pennant. To make matters worse, Chesbro — who was originally supposed to stay back in New York — came to Boston and managed to talk his way into starting one of the games, getting blown out in the first game of the day.

Despite the loss two days prior, they gave the ball to Chesbro for the opener of the doubleheader on October 10th. He bounced back from his struggles and began the day with six scoreless innings, as the Yankees took a 2-0 lead into the seventh. Boston fought back with two runs in the seventh — thanks in part to two errors from New York’s defense, setting up a dramatic and heartbreaking ending.

While Chesbro got two outs in the ninth, he had also allowed a single to Lou Criger, who would move up to third after that. One strike away from getting out of the inning, Chesbro uncorked a wild pitch on a 2-2 count, allowing Criger to scamper home and take the lead. The Highlanders couldn’t answer back in the bottom half of the inning, giving Boston a 3-2 win and the pennant.

In the days and years after the game, there was plenty of debate on who was at fault for the wild pitch. Chesbro’s wife published accounts after the pitcher’s death that stated that the pitch should’ve gone down as a passed ball on catcher Red Kleinow instead. Either way, what’s done was done and the Highlanders had come up short.

Despite the wild pitch that cost them the pennant, the Highlanders wouldn’t have gotten anywhere close without him. It was his ninth start since September 20th, as he threw 124 innings in September and early October alone. The fact that his year didn’t lead to any postseason success means Chesbro’s 1904 is somewhat overlooked, but he did some truly unfathomable things that year.

Post-Peak Years

While, understandably, never coming close to 1904, Chesbro was still a good pitcher for the Highlanders in the years after that.

In 1905, he put up a 2.20 ERA (132 ERA+) in just a mere 303.1 innings pitched — he missed some time that year due to a sore arm. While some people thought that might be due to throwing the spitball, Chesbro himself claimed it was due to effects of malarial fever, which he got after pitching in the rain on Opening Day. Considering the season prior, “overuse of arm” also seems like a valid possibility.

Chesbro dropped to around league average in 1906, as he led the league in earned runs allowed. However, considering that he did that in another 325.0 innings on the year, that’s not as bad as that stat sounds.

In 1907, Chesbro held out to start the season as part of a salary dispute with Griffith and the Highlanders’ management. They eventually figured it out and Chesbro began his season in May. His 2.53 ERA was above average (110 ERA+), but he went just 10-10 on the season, as the team finished below .500 on the year. As it turned out, that would be his final good season in the major leagues.

Chesbro was a below average pitcher for the first time in nearly a decade in 1908, as he stumbled to a 14-20 record. His 2.93 ERA doesn’t sound bad on paper, but it equated to an 84 ERA+ in the Deadball Era. To make matters worse, the Highlanders fell to last place in the AL that season.

Jack Chesbro Spring Training Photo Reproduction by Transcendental Graphics/Getty Images

After his struggles that year, there were rumors that the Highlanders were going to send Chesbro down to the minors. Not happy about those reports, Chesbro again held out, saying he would rather retire than deal with getting sent down. He eventually returned in May, but was visibly out of shape and struggled again. He would only appear in nine games in 1909, putting up an ERA over six. He was so bad that the Highlanders released him.

Boston took a chance on Chesbro on a deal that would send him back to New York if they decided to get rid of him before May of the next season. He made just one appearance for Boston in October 1909 against his old Highlanders’ teammates. The start was unremarkable and Boston announced after the season that they were going to return him to the Highlanders.

After everything that had gone down, the Highlanders didn’t want anything to do with Chesbro and attempted to send him down to the minors. Again, their former ace wouldn’t report there. He technically remained part of the Highlanders’ organization until 1912 when he was finally released after a considered comeback bid.

Post-Playing Career

Chesbro would never appear in a major league game again following his one appearance with Boston in 1909. Despite that, he continued pitching for semi-pro teams over the years, but mostly retired to his Massachusetts farm after his playing career. He briefly spent part of 1924 on the coaching staff of the Washington Senators, but left that role before Washington won the World Series later that year.

Jack Chesbro, old Yankee pitcher now coach of Washington Sen Photo by NY Daily News Archive via Getty Images

In 1931, Chesbro passed away from a heart attack while working on his farm. Fifteen years after his death, he was voted into the Hall of Fame by the Old-Timers Committee in 1946. His candidacy is viewed as a bit dubious through a more modern lens, but Chesbro was a remarkable pitcher when he was on.

Jack Chesbro is never going to have the notoriety of other Yankee legends, for a a variety of completely legitimate reasons. However, the history of the franchise has to start somewhere, and the team’s first real star was Chesbro.

Staff Rank: 47
Community Rank: 51
Stats Rank: 37
2013 Rank: 40


“1903 AL-NL Peace Agreement” — SABR

Baseball Reference

BR Bullpen


Martin, Andrew. Medium.

McElreavy, Wayne. SABR bio

Rice, Stephen V. SABR bio. (Elmer Stricklett)

Robbins, Mike. “The Yankees vs. Red Sox Reader.”

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