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The top 20 left-handed pitchers of all-time
DANIEL LIPPITT/AFP/Getty Images

The top 20 left-handed pitchers of all-time

Left-handers have a special place in society as a whole, but in baseball, they are an exclusive fraternity among the upper rungs of the game’s history. There have been dozens of dominant righties, but it is a special occasion when a “southpaw” takes command of the game. 

In today’s game, two of the most dominant pitchers alive are southpaws – Clayton Kershaw and Chris Sale. Both are of establishing reputations that will go far beyond just what they do today, they are en route towards becoming all-time greats. It will be a difficult ladder to climb, as some of the greatest arms in the history of the game hurl from that minority side of the plate. Here is a look at the top 20 greatest pitchers of all-time to bring it southpaw.

 
Aroldis Chapman
Adam Hunger-USA TODAY Sports

Cincinnati Reds, Chicago Cubs, New York Yankees: 2010-present

While the rest of this list will be comprised of starting pitchers, an exception must be made for the man dubbed as the "Cuban Missile." Chapman is without a doubt one of the most overwhelming presences in the history of the game, possessing the fastest pitch of all time, which has been calculated upward of 105 mph. It has enabled him to become one of the most dominant closers of all time and owner of highest strikeout-per-nine-inning ratio in the history of baseball, at 15.

 

19. Vida Blue

Vida Blue
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Oakland A's, San Francisco Giants, Kansas City Royals: 1969-1986

A six-time All-Star and ace of the Oakland A’s clubs that won three consecutive titles in the mid-1970s, Blue possessed a blistering fastball and stands as one of the hardest throwing southpaws of all time. Such was the incredible ability of Blue that at age 21, he won both the AL MVP and Cy Young after posting a 24-win, 1.78 ERA campaign. He would go on to reach the 20-win mark two more times in his career and twice start the All-Star Game, once for the National League and once for the American League.

 
Johan Santana
Jeff Gross/Getty Images

Minnesota Twins, New York Mets: 2000-2012

The only thing that came between Santana and truly reaching transcendental greatness was injury, because at his best, Santana was something of a left-handed Pedro Martinez. A two-time Cy Young winner with the Minnesota Twins in 2004 and 2006, Santana is one of five pitchers to ever win the award unanimously twice. In that same three-year span, Santana won 55 games, led the AL in strikeouts each season and accumulated a 23.3 WAR level performance.

 

17. Tommy John

Tommy John
Focus on Sport/Getty Images

Cleveland Indians, Chicago White Sox, Los Angeles Dodgers, New York Yankees, California Angels, Oakland A's: 1963-1989

Although the surgery which bears his name has surpassed him in notoriety, the actual man who is Tommy John made an impressive impact on the game in his own right. His 288 career wins are seventh all time among southpaws. In a career that spanned 26 years, the journeyman was a four-time All-Star and won 20 games three times after going under the knife for the initial Tommy John surgery in 1975, including runner-up honors for the NL Cy Young Award in 1977.

 
Chris Sale
Bob DeChiara-USA TODAY Sports

Chicago White Sox, Boston Red Sox: 2010-present

While it may seem a bit early to rank Sale among this group, keep in mind that he is nine years into his career and has knocked batters down at an epic rate. He has averaged more than 10 strikeouts per nine innings over each of the last six years and has been an All-Star in each season. His .220 average against for his career as of 2017 is the second-lowest of all active pitchers behind Clayton Kershaw and checks in at eighth best all time. And Sale is doing nothing but getting better by the year.

 
Madison Bumgarner
John Hefti-USA TODAY Sports

San Francisco Giants: 2010-present

Despite being only 29 years old, Bumgarner has a career’s worth of exploits attached to his name. But putting his three World Series championships, four All-Star appearances and two Silver Sluggers aside, Mad Bum’s dominant romp through the 2014 postseason was more than enough to secure him a place among baseball legends. He worked a 1.03 postseason ERA over 52.2 innings, including allowing one run over three World Series appearances and a Series-clinching, five inning shutout appearance in Game 7. Overall, he is the owner of 11 MLB postseason records.

 
Andy Pettitte
Brad Penner-USA TODAY Sports

New York Yankees, Houston Astros: 1995-2010, 2012-13

A five-time World Series champion, Pettitte is defined by his continual association with winning. He is the all-time leader in postseason victories with 19. Between 1995 and 2010, no pitcher accumulated more wins than Pettitte. In his final championship season of 2009, Pettitte pitched the clinching game in all three rounds of the Yankees’ postseason run.

 

 
CC Sabathia
Andy Marlin-USA TODAY Sports

Cleveland Indians, Milwaukee Brewers, New York Yankees: 2001-present

Possessing a build more akin to an NFL offensive lineman than a pitcher, Sabathia has been a workhorse throughout his career. Winner of the 2007 American League Cy Young Award, Sabathia is a six-time All-Star and led the AL in wins in both 2009 and 2010. He reached double digits in victories in the first 12 years of his career, while working an average of 217 innings from 2003-13.

 

12. Hal Newhouser

Hal Newhouser
Photo File/MLB Photos via Getty Images

Detroit Tigers, Cleveland Indians: 1939-1955

The most dominant pitcher of the World War II era, Newhouser won the American League MVP in both 1944 and 1945, going 51-9 with a 1.87 ERA over the two-year span. Overall, he was a six-time All-Star and won 21 or more games four times from 1944 to 1948. Later on as a scout for the Houston Astros, he discovered a young Derek Jeter, who the Astros passed over in the 1992 draft in favor of Phil Nevin.

 

11. Rube Waddell

Rube Waddell
Chicago History Museum/Getty Images

Pittsburgh Pirates, Philadelphia A's, St. Louis Browns: 1897-1910

The eccentric Waddell was an exception in many ways. He was a dominant strikeout pitcher in the deadball era, where contact was emphasized more than ever. From 1902 to 1907, Waddell led the AL in strikeouts while winning 19 games or more every season from 1902 to 1908. Despite his extraordinary talents, he was prone to disappearing and drinking and that earned him the nickname "sousepaw." He died of substance abuse at only 37 years old.

 

10. Eddie Plank

Eddie Plank
Bettmann/Getty Images

Philadelphia A's, St. Louis Browns: 1901-1917

First great lefty in the game’s history, Plank was the first southpaw to win both 200 and 300 games before finishing with 326 total during his career. He won over 20 games eight times and only once had an ERA over 3.00 — and never after the second of his 17 seasons. He had 1.32 ERA lifetime in the World Series and his 66 shutouts are the most by a lefty ever.

 
Whitey Ford
Kidwiler Collection/Diamond Images/Getty Images

New York Yankees: 1950-1967

"The Chairman of the Board," Ford was the Yankees' ace during the most successful run in their storied history. A New York City native, Ford is one of the great winners of all time. He won 15 or more games in 10 of his 16 seasons and had a 236-106 career record, with an additional 10 World Series wins, the most in history. His .690 career winning percentage is the highest in major league history.

 

8. Carl Hubbell

Carl Hubbell
Mark Rucker/Transcendental Graphics, Getty Images

New York Giants: 1928-1943

While his consecutive strikeouts of Hall of Famers Babe Ruth, Lou Gehrig, Jimmie Foxx, Al Simmons and Joe Cronin in the 1934 All-Star Game is his most known claim to fame, the New York Giants ace accomplished far more than that. Owner of one of the greatest out pitches of all time via his signature screwball, Hubbell was a frustrating matchup for the National League of the 1930s. From 1933-37, he topped 20 wins each season and won in double digits for 15 straight years.

 

7. Tom Glavine

Tom Glavine
Gregory Fisher-USA TODAY Sports

Atlanta Braves, New York Mets: 1987-2008

Part of the greatest pitching trio of all time, Glavine, with his smooth consistency, was the perfect complement to the scientific dominance of Greg Maddux and the overpowering effort of John Smoltz. The two-time Cy Young winner forced his issue with a pinpoint command of the outside part of the plate, as well as a change-up he could use at any point in an at-bat. Five times he topped 20 wins and was the MVP of the Atlanta’s lone World Series victory in 1995.

 
Warren Spahn
Focus on Sport/Getty Images

Boston/Milwaukee Braves, New York Mets, San Francisco Giants: 1942-1965

A 17-time All-Star and winningest lefty of all time, Spahn was the picture of durability both in regard to longevity and effectiveness. After a three-year military stint, his career in earnest began at age 25 and from that point on he won at least 20 games in 10 seasons while regularly taking the ball nearly 40 times a year. He is the greatest old-age pitcher ever, notching 82 of his 363 victories after his 40th birthday, including one of his two no-hitters post-40.

 

5. Steve Carlton

Steve Carlton
Eric Hartline-USA TODAY Sports

St. Louis Cardinals, Philadelphia Phillies, San Francisco Giants, Chicago White Sox, Cleveland Indians, Minnesota Twins: 1965 - 1988

“Lefty” long stood as the pre-eminent power southpaw in the game’s history. After being foolishly cut loose by the St. Louis Cardinals after an early career contract dispute, Carlton took his near unhittable slider to Philadelphia where he won 241 of his 329 games, as well as four Cy Young Awards. His 4,136 strikeouts were second best ever at the time of his retirement, and he briefly was the all-time strikeout leader until being surpassed by his peer Nolan Ryan.

 

4. Clayton Kershaw

Clayton Kershaw
Erich Schlegel-USA TODAY Sports

Los Angeles Dodgers: 2008-present

Although just 30 years old, Kershaw has solidified himself as not only the pre-eminent pitcher of his era, but also in the inner circle of all-time greats. He is already a seven-time All-Star and three-time Cy Young Award winner, and in 2014 he became the first National Leaguer in 46 years to take home both the Cy Young and MVP Awards. In the same season, Kershaw won the NL pitching Triple Crown and became the first pitcher ever to lead a league in ERA for four straight seasons, carrying a 2.11 ERA over 895.1 innings.

 

3. Randy Johnson

Randy Johnson
DANIEL LIPPITT/AFP/Getty Images

Montreal Expos/Seattle Mariners/Houston Astros/Arizona Diamondbacks/New York Yankees/San Francisco Giants: 1988-2009

Standing in at a towering 6-foot-10, "The Big Unit" is the most uniquely intimidating presence in the history of baseball. With a fastball that lived around 100 mph and was offset by a devastating slider that seemed to be released halfway to the plate, Johnson is the most dominant strikeout pitcher of his generation. He won four consecutive NL Cy Young Awards, from 1999-2002, in addition to landing the same honors in the American League in 1995. With 4,875 strikeouts, only Nolan Ryan has issued more Ks all time than Johnson.

 

2. Robert "Lefty" Grove

Robert "Lefty" Grove
Bettmann/Getty Images

Philadelphia A’s/Boston Red Sox: 1925-1941

The first pitcher to ever win MVP, Grove won 20 or more games in eight seasons, seven coming consecutively from 1927 to 1933, with a high of 31 victories in 1931. His career record of 300-141 gives Grove the eighth-highest win percentage of all time, yet no pitcher ahead of him is within 60 wins of his total. In addition, Grove won eight ERA titles and won at least 75 percent of his starts in six different seasons — while making at least 39 starts in each of those years.

 
Sandy Koufax
Focus On Sport/Getty Images

Brooklyn/Los Angeles Dodgers: 1955-1966

"The Left Arm of God" was a telling nickname for Koufax, as the great Dodger southpaw is the owner of perhaps the greatest stretch of pitching in baseball history. From 1961-1966, Koufax had seasons of 25, 26 and 27 wins, along with 300 strikeouts in three of those seasons. He tossed three no-hitters and a perfect game along the way as well, and he won three of four NL Cy Young Awards from 1963 through 1966, along with the NL MVP in ’63 — and remains one of two NL pitchers (Bob Gibson) to win the award in the last 60 years.

Matt Whitener is St. Louis-based writer, radio host and 12-6 curveball enthusiast. He has been covering Major League Baseball since 2010, and dabbles in WWE, NBA and other odd jobs as well. Follow Matt on Twitter at @CheapSeatFan.

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