Only one pitcher (Denny McLain in 1968) has won 30 games in a season since Dizzy Dean accomplished the feat in 1934. It’s safe to say that with the way that the game has evolved, that this feat probably will never be accomplished again.
Forty wins in a season? Forget about it.
This leads us to Jack Chesbro (originally Chesebrough). Ok, he wasn’t a Classic Yankee, but rather, a Classic Highlander, and there aren’t too many of those.
Still in all, he still owns the modern (since 1901) record for wins in a season with 41 in 1904.
Chesbro, from Massachusetts, broke into the majors at the age of 25 in 1899 with the Pittsburgh Pirates. He went 6-9, 4.11 in 1899. Now in those days, there were fences 500 feet away, legal spitballs, and balls being kept in play with scuffmarks, dirt, etc. Not only that, most hitters were punch-and-judy hitters who swung for contact, not the freestyle power hitters of today.
Chesbro improved to 15-13, 3.67 in 1900, ERA+ 99. In 1901 he was 21-10, 2.38, ERA+ 137. He led the majors in 1901 with six shutouts.
Chesbro kept it up in 1902. He led the league with 28 wins, and led the majors (the AL had formed the year before, in 1901) with an .824 winning percentage (28-6). His ERA was 2.17. Once again he led the majors in shutouts with eight. He led the majors in HBP with 21 and posted a 127 ERA+.
The Pirates of 1902 were one of the greatest teams in the dead-ball era. It was the last season before the start of the World Series (the WS starting in 1903 and being interrupted only in 1904 and 1994). Led by player-manager Fred Clarke, all-time great Honus Wagner, Ginger Beaumont, Tommy Leach, Chesbro, Deacon Phillippe and Jesse Tannehill, just to mention a few, that team went 103-36! Those Pirates teams won pennants from 1901-1903, Chesbro contributing in 1901 and 1902.
Chesbro threw for 215 2/3 innings in 1900, 287 2/3 in 1901, and 286 1/3 in 1902. He was just warming up.
Chesbro jumped leagues after the 1902 season, and became a New York Highlander. The Pirates missed him in that first WS of 1903, losing to the Boston Americans (the Red Sox’ original nickname) five games to three. Injuries forced Deacon Phillippe to start games 1, 3, 4, 7 AND 8 for the Pirates. (He won the first three, lost the last two). Oh yeah, game EIGHT. The 1903, 1919, 1920 and 1921 Classics were best-of-NINE affairs. That lack of pitching depth turned a three games to one Series lead for the Pirates into a five games to three Series loss.
Chesbro, meanwhile, tossed 324 2/3 innings for the 1903 Highlanders. This was the first year in New York for the team that, in 1913, would change their name to the Yankees. They had spent 1901 and 1902 in Baltimore as the Orioles. Chesbro went 21-15, 2.77, ERA+ 112. No, he did NOT lead the league in IP!
In 1904, Chesbro did yeoman work. Consider this. He led the majors with 41 wins, which, as stated above, remains the modern (1900 on) record for wins in a season. He led the majors by appearing in 55 games. He led the majors with 51 starts, 48 complete games and 454 2/3 IP. He led the league in H/9 and the majors in batters faced. Chesbro wound up 41-12, 1.82, with an ERA+ 148.
From Wikipedia: Chesbro won 14 straight games from May 14 through July 4, a New York franchise record that stood until Roger Clemens broke it in 2001. His 239 strikeouts remained a team record until Ron Guidry struck out 248 in 1978. On the last day of the season, in a game against the Boston Americans (now known as the Boston Red Sox), he threw a wild pitch in the top of the ninth inning, allowing the winning run to score from third base and causing the Highlanders to lose the pennant to Boston. The ruling on this play was controversial. Even after Chesbro’s death in 1931, his widow, with the support of former Highlanders manager Clark Griffith (by this time Washington’s owner), continued to claim that the pitch was a passed ball, and blamed the winning run on catcher Red Kleinow.
Still, just to clarify, Chesbro was a spitball pitcher, after all.
Oh, those ’04 seasons…
Chesbro went 19-15 in 1905, as he pitched 303 1/3 innings with an ERA of 2.20 (ERA+ 133). In that season (also Wikipedia), Chesbro was involved in the first squeeze play in baseball. At third base, Chesbro mistakenly thought he had received a steal sign from manager Clark Griffith, while Willie Keeler bunted for a hit. As Chesbro scored, Griffith made a note of the play and taught it in spring training the following season.
In 1906, the Highlanders once again finished second, as Chesbro went 23-17, 2.96. That ERA of 2.96 only yielded a 100 ERA+ however (average). Chesbro led the majors in games (49) and games started (42) while tossing 325 innings. Note that the only year of his career that Chesbro led the league in IP was in that 1904 season with the 454 2/3. Chesbro led the AL in earned runs given up in 1906.
Chesbro went 10-10, 2.53 in 1907, when he hurled “only” 206 innings. ERA+ 111.
His last year as a full-time producer was in 1908, when he was 34. He went 14-20, 2.93, and pitched in 288 2/3 innings. Despite the 2.93 ERA, the ERA+ was just an 84, meaning that the average was 2.46 that year.
Chesbro benefitted from the times. Some aspects of dead ball play I mentioned earlier. Hilltop Park, where Columbia Presbyterian Medical Center is today, had different dimensions during its time (1903-1912) as the Highlanders’ home. Some of those dimensions were quite vast.
It’s ironic that if there are injuries at the current Yankee Stadium today at 161st and River Ave. in the Bronx that players are taken the short distance away to Columbia-Presbyterian at 165th-168th and Broadway (and Ft. Washington Ave.) in Manhattan for hospital treatment. I wonder how many players that are taken there realize that a ballpark once stood on the site of the hospital. There is a plaque on the grounds, donated by the Yankees, to mark where home plate once was.
After pitching all those innings, Chesbro’s arm gave out in 1909. He started five games, relieved in five, and pitched only 55 2/3 innings, going 0-5, 6.14. He pitched one game—his last—for the Red Sox (as they were now known at that time). He lost it.
As a hitter, Chesbro hit .197. Despite the lack of HRs back then, Chesbro, a pitcher, did hit five in his career.
Chesbro wound up his career 198-132, with an ERA of 2.68, ERA+ 111. From 1900-1908 he averaged 21-13, 2.53, ERA+ 116, and 299 IP per season. He died at the age of 57 in 1931.
He was elected to the HOF in 1946. All things considered, he probably got in based on that one great season. From Wikipedia again: Chesbro was inducted into the National Baseball Hall of Fame in 1946 balloting by the Veterans Committee, which considers individuals who are eligible for the Hall of Fame, but no longer eligible to be elected by the Baseball Writers Association of America (BBWAA). That year, the Veterans Committee elected eleven players … During years where Chesbro was eligible on the BBWAA ballot, Chesbro received zero votes in the 1936 balloting, one vote in the 1937 balloting, two votes in the 1938 balloting, and six votes in the 1939 balloting, zero votes in the 1942 balloting, and zero votes in the 1945 balloting.
Chesbro never wore a number. No Highlander ever did. The first year numbers appeared on a Yankee uniform was in 1929.