Between 2003 and 2009, Johan Santana won two American League Cy Young Awards, posted a top-three finish in voting for the award in the National League and finished second to only Hall of Famer Roy Halladay in terms of fWAR.
Santana -- who starred for the Minnesota Twins and New York Mets -- appeared to very much be on a Hall of Fame trajectory himself when you consider that he was only 30 in 2009.
Unfortunately for Santana, injuries derailed his career, with his last major league action coming just a few years later in 2012. The 45.0 WAR 7 -- the combination of a player's top seven single-season bWAR totals -- that Santana posted, is higher than Hall of Famers Nolan Ryan, Mike Mussina and Don Drysdale, among others. But outside of his peak, there just wasn't enough of a resume to convince voters, and Santana was one-and-done on the Hall of Fame ballot.
It should be noted, Santana drew consideration for this list, because there's something to be said for being arguably the best pitcher in the game at the height of your powers.
Ultimately, Santana fell short, like contemporaries CC Sabathia, Cliff Lee, Andy Pettitte and Cole Hamels. Among the others who came up just short were Madison Bumgarner, Carl Hubbell, Vida Blue, Chris Sale, Tommy John and Hal Newhouser.
With such a tremendous list of names not on our list, if gives you an idea of how exclusive our countdown of the nine greatest left-handed pitchers of all-time is:
9. Tom Glavine - Atlanta Braves & New York Mets (1987-2008)
Tom Glavine is one of the greatest pitchers in MLB history.(Jed Jacobsohn/Getty Images)Best Season: 1991 - 20-11 with a 2.55 ERA, 153 ERA+, 3.06 FIP, 1.095 WHIP, 192 strikeouts, nine complete games and a 5.4 fWAR
Career Stats: 305-203 with a 3.54 ERA, 118 ERA+, 3.95 FIP, 1.314 WHIP, 2,607 strikeouts, 56 complete games and 66.7 fWAR
A 10-time All-Star, Glavine was a two-time National League Cy Young Award winner, capturing the senior circuit's top honor among pitchers in both 1991 and 1998. Glavine is most remembered for the 17 years that he spent with the Braves, trying to outduel teammates Greg Maddux and John Smoltz in one of the greatest rotations ever assembled. However, he also won 61 games -- including his 300th career victory -- during his five seasons with the Mets. Glavine was elected to the Hall of Fame on his first ballot in 2014.
8. Eddie Plank - Philadelphia Athletics, St. Louis Terriers & St. Louis Browns (1901-1917)
Eddie Plank is one of the greatest pitchers in MLB history.(Paul Thompson/Wikimedia Commons)Best Season: 1905 - 24-12 with a 2.26 ERA, 119 ERA+, 2.28 FIP, 1.044 WHIP, 210 strikeouts, 35 complete games and a 5.7 fWAR
Career Stats: 326-194 with a 2.35 ERA, 122 ERA+, 2.45 FIP, 1.119 WHIP, 2,246 strikeouts, 410 complete games and 67.8 fWAR
One of baseball's earliest aces, Plank racked up 250 or more innings on 10 occasions during his career, which was spent primarily with Connie Mack's Philadelphia Athletics. Plank won three World Series titles with the A's, and his 326 wins are 13th in MLB history. "Gettysburg Eddie" was inducted into the Hall of Fame in 1946.
7. Whitey Ford - New York Yankees (1950; 1953-1967)
Whitey Ford is one of the greatest pitchers in MLB history.(Bettmann/Getty Images)Best Season: 1964 - 17-6 with a 2.13 ERA, 170 ERA+, 2.45 FIP, 1.099 WHIP, 172 strikeouts, 12 complete games and a 6.8 fWAR
Career Stats: 236-106 with a 2.75 ERA, 133 ERA+, 3.26 FIP, 1.215 WHIP, 1,956 strikeouts, 156 complete games and 54.9 fWAR
Despite losing the 1951 and 1952 seasons to military service, Ford was one of the greatest left-handed pitchers of the 20th century. A lifetime Yankee, Ford was a 10-time All-Star, who won two American League ERA titles and the AL Cy Young Award in 1961. Oh, he also casually won six World Series titles during his 16-year career. Ford was inducted into the Hall of Fame in 1974.
6. Lefty Grove - Philadelphia Athletics & Boston Red Sox (1925-1941)
Lefty Grove is one of the greatest pitchers in MLB history.(Wikimedia Commons)Best Season: 1930 - 28-5 with a 2.54 ERA, 185 ERA+, 2.45 FIP, 1.144 WHIP, 209 strikeouts, 22 complete games and an 8.3 fWAR
Career Stats: 300-141 with a 3.06 ERA, 148 ERA+, 3.20 FIP, 1.278 WHIP, 2,266 strikeouts, 298 complete games and 88.8 fWAR
When they reserve the name "Lefty" specifically for you, it's a pretty good indication of how dominant you were in your era. Born as "Robert Moses Grove," Lefty won a staggering nine American League ERA titles, twice winning the pitching triple crown. The All-Star Game didn't even begin until Grove's age-33 season, but he still managed to make six appearances in the midsummer classic. The Cy Young Award wouldn't come around until 15 years after Grove last pitched, but he won the AL MVP in 1931, and you get the sense he would have won any major pitching award multiple times had it existed in his era. Grove finished his career with exactly 300 wins, and was inducted into the Hall of Fame in 1947.
5. Clayton Kershaw - Los Angeles Dodgers (2008-Present)
Clayton Kershaw is one of the greatest pitchers in MLB history.(Jeff Gross/Getty Images)Best Season: 2014 - 21-3 with a 1.77 ERA, 197 ERA+, 1.81 FIP, 0.857 WHIP, 239 strikeouts, six complete games and a 7.9 fWAR
Career Stats: 185-84 with a 2.49 ERA, 155 ERA+, 2.77 FIP, 1.004 WHIP, 2,670 strikeouts, 25 complete games and 69.5 fWAR (stats current as of February 2022)
Arguably baseball's greatest pitcher of the 21st century to this point, Kershaw is a three-time National League Cy Young Award winner, who also has an NL MVP, pitching triple crown and five senior circuit ERA titles on his resume. An eight-time All-Star, Kershaw finally won his first World Series in the pandemic-shortened 2020 season, exercising some previous October demons. Kershaw figures to pitch a few more seasons, but if he retired today he would be a first-ballot Hall of Famer.
4. Warren Spahn - Boston/Milwaukee Braves, New York Mets & San Francisco Giants (1942; 1946-1965)
Warren Spahn is one of the greatest pitchers in MLB history.(Getty Images)Best Season: 1953 - 23-7 with a 2.10 ERA, 188 ERA+, 2.97 FIP, 1.058 WHIP, 148 strikeouts, 24 complete games and a 6.2 fWAR
Career Stats: 363-245 with a 3.09 ERA, 119 ERA+, 3.44 FIP, 1.195 WHIP, 2,583 strikeouts, 382 complete games and 74.8 fWAR
Spahn checked in at No. 4 on our countdown of the greatest players in Braves history, and finds himself in the same spot here. Spahn lost his age-22 through age-24 seasons to service in World War II, but still managed to win three ERA titles, make 17 All-Star Game appearances and capture the 1957 National League Cy Young Award. Spahn's 356 wins -- again, obtained despite missing three seasons -- are sixth in MLB history. Spahn was elected to the Hall of Fame in 1973.
3. Steve Carlton - St. Louis Cardinals, Philadelphia Phillies, San Francisco Giants, Chicago White Sox, Cleveland Indians & Minnesota Twins (1965-1988)
Steve Carlton is one of the greatest pitchers in MLB history(George Gojkovich/Getty Images)Best Season: 1972 - 27-10 with a 1.97 ERA, 182 ERA+, 2.01 FIP, 0.993 WHIP, 310 strikeouts, 30 complete games and an 11.1 fWAR
Career Stats: 329-244 with a 3.22 ERA, 115 ERA+, 3.15 FIP, 1.247 WHIP, 4,136 strikeouts, 254 complete games and 96.5 fWAR
We previously ranked Carlton as the greatest pitcher in Phillies history, and he's unquestionably one of the finest lefties to ever toe the rubber. Carlton won four National League Cy Young Awards, a pitching triple crown, an ERA title and a Gold Glove Award. He won two World Series titles; one with the St. Louis Cardinals (1967) and one with the Phillies (1980). Carlton's 329 career wins are 11th in MLB history. Carlton was elected to the Hall of Fame in 1994.
2. Randy Johnson - Montreal Expos, Seattle Mariners, Houston Astros, Arizona Diamondbacks, New York Yankees and San Francisco Giants (1988-2009)
Randy Johnson is one of the greatest pitchers in MLB history.(Otto Gruele/Allsport)Best Season: 2001 - 21-6 with a 2.49 ERA, 188 ERA+, 2.13 FIP, 1.009 WHIP, 372 strikeouts, three complete games and a 10.4 fWAR
Career Stats: 303-166 with a 3.29 ERA, 135 ERA+, 3.19 FIP, 1.171 WHIP, 4,875 strikeouts, 100 complete games and 110.4 fWAR
Johnson has already appeared in the top five of our countdowns of the greatest Seattle Mariners and Arizona Diamondbacks players ever, so his place here should be no surprise. "The Big Unit" was a 10-time All-Star, five-time Cy Young Award winner, four-time league ERA champion and the co-MVP of the 2001 World Series. He was inducted into the Hall of Fame in 2015. Johnson may be the last pitcher to ever win 300 games, and if you believe he should be No. 1 on this list, there's a very fair discussion to be had.
1. Sandy Koufax - Brooklyn/Los Angeles Dodgers (1955-1966)
Sandy Koufax is one of the greatest pitchers in MLB history.(Malcolm Emmons/USA Today)Best Season: 1963 - 25-5 with a 1.88 ERA, 159 ERA+, 1.85 FIP, 0.875 WHIP, 306 strikeouts, 20 complete games and a 9.2 fWAR
Career Stats: 165-87 with a 2.76 ERA, 131 ERA+, 2.69 FIP, 1.106 WHIP, 2,396 strikeouts, 137 complete games and 54.5 fWAR
Injuries limited Koufax to just a 12-year career, but he had arguably the greatest peak of any pitcher in MLB history. Despite retiring after his age-30 season, Koufax won five National League ERA titles, three pitching triple crowns, three NL Cy Young Awards, two World Series MVPs and the 1963 NL MVP. He was inducted into the Hall of Fame in 1972. It wouldn't feel right to have anyone other than "the Left Arm of God" at the top spot on this countdown.
Other Entries in This Series
- Ranking The Nine Greatest Catchers in MLB History
- Ranking The Nine Greatest First Basemen in MLB History
- Ranking The Nine Greatest Second Basemen in MLB History
- Ranking The Nine Greatest Shortstops in MLB History
- Ranking The Nine Greatest Third Basemen in MLB History
- Ranking The Nine Greatest Center Fielders in MLB History
- Ranking The Nine Greatest Right Fielders in MLB History
- Ranking The Nine Greatest Left Fielders in MLB History
- Ranking The 9 Greatest Right-Handed Pitchers in MLB History
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