Best left-handed pitchers of all-time: The best lefties in MLB history

Among the best pitchers of all-time, you find a number of elite lefties. Today, we’ll explore the best left-handed pitchers in major league history.

As part of a series we will cover here at Call to the Pen on MLB history, today we will look at the best left-handed pitchers of all time.

We will cover all of MLB history, not just the first 100 years or the last 50 years, and this is not a consensus of all Call to the Pen authors and editors, but the opinion of the author of that list. This is a great list to debate and discuss!

Before we move to the top 20, let’s look at one current player who has a chance to break into this top 20 list!

Chris Sale, 97 wins, 2.97 ERA, 1,419 1/3 IP, 1,681 strikeouts, 39.5 bWAR

With an active pitcher in the top 20 already, it takes a solid track record of production to get notice here. How about this for “production”…of the top 200 left-handed starters of all-time in bWAR, Sale has the highest strikeout rate, at 29.5% for his career, nearly a full percentage point over #2. He’s also 3rd in ERA+ among all of the best pitchers from the left side.

Sale already ranks just outside of the top 50 lefties in career bWAR, though he is pitching in just his age-29 season and has many innings to go to get career numbers close. Sale is signed through 2018, with a 2019 option that is nearly certain to be picked up, putting him on the open market going into his age-31 season.

By that point, he very well could be at 120 wins and over 2,000 strikeouts. Only 25 lefties have ever cleared 2,000 strikeouts, which would mean having multiple solid seasons ahead of him after already clearing the number could put Sale in elite company in a hurry among his fellow southpaws.

While one thing I’ve used here to separate pitchers is recognition from peers, Sale’s 6 All-Star games speak loudly, and even though he has not won a Cy Young, he has now finished in the top 5 in voting the last 5 years straight. He’s also finished in the top 20 in MVP voting the last three seasons.

For now, however, let’s take a look at the guys who do make the list…

Next: 20. Late Round Gem

20. Mark Buehrle, 214 wins, 117 ERA+, 3,283 1/3 innings, 1,870 strikeouts, 59.3 bWAR

Incredibly, Buehrle was a 38th round selection by the White Sox out of Jefferson College in Missouri in 1998. He moved quickly, getting to the majors already in 2000, and he was already tossing 200+ innings in 2001.

What made Buehrle exceptional and one of the best pitchers of his era was not elite production from year to year, but instead, Buehrle was known for his consistency from season to season. Buehrle never once won 20 games or posted an ERA for a season under 3, but in his final season in 2015, Buehrle fell 1/3 inning short of tossing 200+ innings for 15 consecutive years.

He wasn’t just a mid-rotation control artist type, either. Buehrle had the ability to dial up for velocity, but he chose to work more with control and movement around the zone, with his career high in strikeouts being 165.

Over his career, Buehrle was recognized as one of the best fielding pitchers in the game, winning 4 Gold Glove awards. He was also elected to 5 All-Star games. When he retired after the 2015 season, multiple teams were more than willing to offer him not just a contract, but a multi-year contract, which could have given Buehrle a chance to reach 250 wins, 2,000 strikeouts, and perhaps even 4,000 innings.

He’ll likely not get a ton of Hall of Fame support, but Buehrle was one of the best pitchers in the entire league for 15 seasons in terms of consistency, and that’s something that is definitely of value!

Next: 19. Good Luck Chuck

19. Chuck Finley, 200 wins, 115 ERA+, 3,197 1/3 innings, 2,610 strikeouts, 58.1 bWAR

After trying in the June 1984 draft to draft him in the 15th round, the Angels again selected Charles Edward Finley with the 4th overall selection in the January 1985 draft. Standing 6’6″ tall and a well-defined 220 pounds, Finley was a guy that drew female interest almost immediately, and he would go on to have his career overshadowed by an incident of domestic abuse committed by his actress wife that became sports talk show fodder to berate Finley and degrade him for “letting” a woman assault him.

Finley established himself into the Angels rotation in 1988 and was an All-Star the next two seasons. The Angels would come to feature a left-handed front three in their rotation that was one of the best in the game’s history with Finley, Mark Langston, and Jim Abbott.

Unfortunately, the Angels really did not experience much success with that trio on the mound, only finishing .500 or better once in the four seasons they were together. Langston and Finley would continue to be paired together until 1996. Finley was moved to the Indians, where he would be steady for the Indians in 2001, but after struggling in 2001, the Indians made a move to trade him to the Cardinals mid-season in 2002. In spite of throwing well down the stretch, he did not find a job for the next season in what would have been his age-40 season.

Finley finished his career with exactly 200 wins, making 5 All-Star games, and incredibly, in spite of finishing among the league leaders multiple times in various pitching stats, his teams were often not good enough to push him over the top for votes, and he only received Cy Young Award votes in one season.

Next: 18. Grandpa

17. Hal Newhouser, 207 wins, 130 ERA+, 2,993 innings, 1,796 strikeouts, 63.3 bWAR

Before a certain Dodger southpaw set the world on its edge in the 1960s for a short period of dominance to raise questions about how to weigh elite production over a short time versus consistent great production over many years, Newhouser did the same thing for the Tigers in the 1940s.

Hal Newhouser was a solid pitcher for the Tigers already before his 1944 breakout, making two All-Star games, but he turned it up another notch in 1944, and he stayed at that level for a half-dozen seasons that were one of the most incredible runs in baseball history.

From 1944-1949, Newhouser averaged 23 wins, 295 innings, and 190 strikeouts with a 2.52 ERA. Even more impressive, the beginning of that stretch, 1944-1946, Newhouser averaged 27 wins, 306 innings, 225 strikeouts, and a 1.99 ERA. He was able to lead the Tigers to a World Series win in 1945, making 3 starts along the way.

In his career, Newhouser was elected to 7 All-Star games, winning the pitching triple crown in 1945 along with the 1944 and 1945 MVP awards. The Veteran’s Committee selected Newhouser to the Hall of Fame in 1992.

Next: 16. Aww shucks Andy

16. Andy Pettitte, 256 wins, 117 ERA+, 3,316 innings, 2,448 strikeouts, 60.3 bWAR

Drafted by the Yankees out of San Jacinto College in 1990 in the 22nd round, Pettitte was immediately one of the best pitchers in the Yankees farm system, jumping up levels at a time, reaching AAA in 1994 at 22, ranked as the #49 overall prospect in baseball.

He opened the 1995 season in AAA, but after 2 starts where Pettitte allowed no runs and no walks over 11 2/3 innings, he was inserted into the Yankees rotation. In 1996, on their way to the first World Series championship of their impressive run in the late-90s through the early 2000s, the Yankees got 21 victories and 221 innings from Pettitte.

He would become a consistent force in the rotation for nearly a decade. After an injury just ahead of free agency, Pettitte jumped to his hometown Houston Astros, eventually bringing fellow former Yankee Roger Clemens on staff with him.

The Yankees pulled him back for the 2007 season, and he was a rarity when he chose to undergo surgery at 38 years old and returned to throw two more very solid seasons with the Yankees. The Yankees did not intend to bring him back in 2014, so Pettitte chose to retire, though he was certainly above-average in that final season.

Over his career, Pettitte was able to win 5 World Series and pitch in the playoffs in 14 different seasons. Overall, he tossed another 276 2/3 innings in the postseason with 19 more wins. Pettitte was an All-Star 3 times, though he only received Cy Young votes 5 times, finishing 2nd in 1996 for the best finish of his career.

Next: 15. The Original

15. Tommy John, 288 wins, 111 ERA+, 4,710 1/3 innings, 2,245 strikeouts, 62.0 bWAR

Many young fans probably don’t even realize that the surgery that makes the career of so many of the pitchers in the modern game even possible had a first recipient, a guinnea pig, the guy that those who have received the surgery now simply call “The Original”.

If it weren’t for an advantageous trade in the 1971-1972 offseason that sent Dick Allen to the White Sox, we may have never heard of Tommy John, and it’s very feasible that the surgery that now bears his name would never have been invented. While John was a very good pitcher for the White Sox, leading the American League in shutouts in 1966 and 1967, he was on some bad White Sox teams, meaning his excellence on the mound was for naught. In spite of three straight seasons with a sub-3 ERA from 1966-1968, John only nabbed one All-Star nod, and it wasn’t in either of the seasons he led the league in shutouts.

His first season with the Dodgers, John discussed elbow issues, but he was able to pitch through many of them, something most pitchers did. However, in spite of success when he was on the mound, he eventually could not overcome the pain on the mound, peaked by an acute elbow injury in the 1974 season.

That led to John seeking the help of the Dodgers’ team doctor, Frank Jobe. After some long discussion, John went along with Jobe’s theoretical procedure, and to this day, he is the pitcher who has thrown the most innings after having the procedure (2,544 2/3).

In the end, John pitched in 26 seasons, making 4 All-Star teams, and he received votes for the Cy Young Award in 4 seasons, peaking in 1977 and 1979 when he finished 2nd. He remains the pitcher with the most victories who is not in the Hall of Fame, though the impact of his elbow procedure alone on the game should, at some point, get him inducted.

Next: 14. Dub

14. CC Sabathia, 241 wins, 117 ERA+, 3,380 1/3 innings, 2,893 strikeouts, 60.9 bWAR

In 1998, the Cleveland Indians drafted a tall, thick lefty out of high school in Caliornia, Carsten Charles Sabathia. Known as CC, Sabathia flew through the Indians system, ranked as the #7 prospect in all of baseball before the 2001 season. The Indians gave Sabathia an opening day rotation spot, He had one of the most impressive rookie seasons for a pitcher in recent history, going 17-5 for the Tribe, but he happened to be a rookie the same season as Ichiro, who hit .350 and had 242 hits to not just win the Rookie of the Year award, but also the American League MVP.

Working to use his impressive fastball and breaker and keep his size from getting too out of hand was a combination of difficulties in his first few seasons in Cleveland, but before the 2005 season, Sabathia worked on his grips and eschewed his curve for a slider, finding significantly more success almost immediately. He’d end up winning the 2007 AL Cy Young, and he really should have won something in 2008, when he went from the Indians to the Brewers at mid-season, and there’s really no way to say anything but that he put the Brewers on his back and took them to the playoffs, winning 11 games in a half-season.

Sabatha would sign with the Yankees as a free agent before the 2009 season and win his first World Series championship. He’s go on to lead the American League in victories his first two years in the Bronx. Now, after knee issues put his career in jeopardy, Sabathia has re-invented himself to be a tremendous asset to the Yankees as they work to plug in a number of young starters into their rotation over the next few seasons from their minor league system.

Sabathia has every chance to plug away at 300 wins, likely clearing 250 wins in 2018 with a renewed ability to possibly go 2-3 more seasons pitching like he has been, though such numbers may not end up really being his prime focus as he’s really stated he wants another championship more than anything else.

Over 18 seasons, Sabathia has been selected to 6 All-Star games, won the 2007 AL Cy Young, receiving votes in 5 consecutive seasons from 2007-2011. He also received MVP votes in each of those seasons.

Next: 13. The Chairman of the Board

13. Whitey Ford, 236 wins, 133 ERA+, 3,170 1/3 innings, 1,956 strikeouts, 56.9 bWAR

For many, this ranking will be drastically too low. For others, this will be drastically too high. With Edward Charles Ford, that is the norm of how his career went. Was he the beneficiary of one of the strongest teams in Yankee history, or did he earn his marks all his own? Those questions dogged Ford throughout his career and continue to follow him now well beyond his retirement as he’s nearly 90 years old now.

He was not a strikeout pitcher, striking out an even 15% of hitters over his career. However, he was the guy at the front of so many great New York teams, one of the best friends of Mickey Mantle, and therefore, when he is remembered, he’s remembered as an elite pitcher.

Ford did have an incredible amount of postseason experience for a pitcher in his era. While pitchers today could amass 22 postseason starts over 5 seasons of playoff work, Ford needed 11 seasons, and he won 6 rings along the way, pitching to a 2.71 ERA over 146 postseason innings. He was the MVP of the World Series in one of the most storied seasons in Yankee history, 1961.

Over his career, Ford was selected for 10 All-Star games (though there were multiple games in a few seasons in there). He won the Cy Young in 1961, though he had multiple seasons when he would have likely challenged for the award before then if there were such an award in both leagues rather than just one for all of the major leagues. Ford received MVP votes in 9 seasons, peaking at #3 in 1963.

His controversy over his numbers and achievements being his own merit or due to his team bit him when Hall of Fame voting came around, as he did not get in on the first vote and barely made it in on the second ballot, garnering 77.8% of the vote.

Next: 12. Kitty

12. Jim Kaat, 283 wins, 108 ERA+, 4,530 1/3 innings, 2,461 strikeouts, 50.7 bWAR

Because he didn’t strike out a ton of hitters, many seemed to miss just how incredible the career of the 6’4″ 200-pound lefty from Michigan truly was. Kaat is widely considered the best defensive pitcher of the last 50 years, if not in the history of the game.

He did more than just field his position well as well. Kaat moved with the Senators to Minnesota, making the rotation in the Twins’ first season in the Twin Cities. Though he threw well, he lost 17 games that season. His fortunes reversed in 1962 as Kaat earned his first All-Star nod, winning 18 games.

Kaat was a fixture in the Twins rotation during a decade of success in Minnesota in the 1960s, but as the team started to struggle, Kaat also ran into some injury struggles. As he got healthy again in 1973, the Twins took the opportunity to trade him to the White Sox.

Over the next decade, he would pitch for multiple very good teams along the way, but often as a swingman instead of a featured starter. He finished his career in his 40s pitching with the Cardinals as a reliever.

Because he didn’t have the dominant numbers and often was entrusted by his manager to stay in the ballgame late because of his ability to generate ground balls and field his position so well, which often meant that his ERA numbers were inflated.

Kaat was selected to 3 All-Star games over his career and amazingly only received Cy Young votes in one season, which is interesting since he actually received MVP votes three seasons. Kaat won 16 Gold Gloves over his career. Only Greg Maddux won more as a pitcher…or any other position, and no other pitcher than Kaat and Maddux has won even 10 Gold Gloves.

In spite of his impressive accolades defensively, Kaat did not make the Hall of Fame. He remains the pitcher with the second-most wins who is not in the Hall of Fame.

Next: 11. King Carl

11. Carl Hubbell, 253 wins, 130 ERA+, 3,590 1/3 innings, 1,677 strikeouts, 68.3 bWAR

Owner of one of the most amazing moments of the All-Star game, Hubbell was one of the top pitchers for the Giants when he took the mound for the National League in the 1934 All-Star game, the second such game ever played. Hubbell allowed a single and a walk to open the game. He then proceeded to strike out the next five hitters he faced.

They were not just any five hitters. Hubbell would strike out Babe Ruth, Lou Gehrig, and Jimmie Foxx to close out the first. He then opened the second inning by striking out Al Simmons and Joe Cronin. That’s five Hall of Famers all down on strikes in a row.

Hubbell was well known by either “King Carl” or “Meal Ticket”, and Hubbell’s meal ticket was a screwball that many have said has never been equaled in the game. While he’s known for strikeouts in an All-Star game, typically a screwball is known for creating weak contact, but it is also often difficult to control. Hubbell had the pitch mastered, with a career walk rate of just 4.9%.

When the All-Star game was introduced, it was fittingly timed for Hubbell. He was in the midst of his best season in 1933 during the first game, and the second game was to be played on his home field in 1934, allowing Hubbell to gain plenty of notoriety, which allowed him to get All-Star nods during a few fairly ordinary seasons to open the 1940s.

Over his career, Hubbell was selected to 9 All-Star games. He won the MVP award twice and received votes in six seasons. His peak was quick and brilliant, however, as is the case with many lefties, and he was on the Hall of Fame ballot four times before garnering enough votes for election in 1947.

Next: 10. Tommy

10. Tom Glavine, 305 wins, 118 ERA+, 4,413 1/3 innings, 2,607 strikeouts, 80.8 bWAR

A Massachusetts boy that had as many dreams of being the next Bobby Orr as he did being the next Luis Tiant, Glavine was a 2nd round pick by the Braves in 1984, and he worked his way quickly to the majors, making his debut in 1987 at 21 years old. He’d go on to lose 17 games in 1988 to lead the league in his first full season as a starter.

He would go on to have to solid seasons with very poor Braves teams in 1989 and 1990, but as the Braves made the leap to elite, so did Tom Glavine, winning 20 games in 1990, beginning a run of 3 straight seasons with 20+ wins. Glavine would top 20 wins twice more with the Braves before leaving after the 2002 season for the division rival New York Mets.

While some Braves fans are still bitter that his 300th victory was in a rival’s uniform, Glavine did return to Atlanta to finish his career in 2008. He now works as a broadcaster of Braves games and has made his way back to Braves good graces, even getting his number retired in 2010.

Glavine’s meteoric rise to the top of the National League’s pitching roles was keyed by a meeting with a former Dodger lefty to be profiled later on this list, who worked with Glavine on the circle change. Glavine would become a prophet of the circle change, teaching it to a host of young pitchers, especially left-handed pitchers within the Braves organization over the years.

Over his long career, Glavine was selected to 10 All-Star games, 2 Cy Young awards, received votes in 6 Cy Young ballots, and received votes on 5 MVP ballots. Glavine was always considered an adept hitter as a pitcher, winning 4 Silver Sluggers. He was elected to the Hall of Fame in 2014 on his first ballot with 91.9% of the vote.

Next: 9. Josie

9. Johan Santana, 139 wins, 136 ERA+, 2,025 2/3 innings, 1,988 strikeouts, 51.6 bWAR

This could be controversial to have him so high, but for many, there was not a better left-handed pitcher than Santana in the game at his peak, and that is saying something, considering a lefty that figures very prominently later in this list was still very active during Santana’s career. The story of his incredibly humble roots to his career makes his career story all the better.

Originally signed out of Venezuela by the Houston Astros, Santana was selected by the Marlins in the Rule 5 draft in 1999, but the Minnesota Twins traded with the Marlins to acquire his rights. Santana would spend his 2000 season as a seldom-used long reliever and spot starter, and then returned to the minor leagues, making his way back for another long relief role in 2001.

In 2002, Santana was one of the most dominant pitchers in the American League, and he repeated the feat in 2003, both while working as a long reliever. Then Johan’s 2004 happened. He won 20, led the AL in ERA, and led the AL in strikeouts.

Sanatana had quickly gone from one of the best left-handed pitchers in the American League, to one of the best left-handed pitchers in all of baseball, and by the time 2008 was completed, the discussion was where he ranked among the best left-handed pitchers in the history of the game.

However, it was after that 2008 season that his career went South. He made just 25 starts in 2009, returned to make 29 starts in 2010, including the first no-hitter in New York Mets team history, and then missed all of the 2011 season before coming back for one last attempt in 2012.

His shoulder was gone, and with it his career, a player who lived off his changeup, relying on his shoulder. He was selected to 4 All-Star games, won 2 Cy Young Awards, received Cy Young votes in 6 seasons, won a Gold Glove, and won the 2006 American League pitching triple crown.

Next: 8. The Left Arm of God

8. Sandy Koufax, 165 wins, 131 ERA+, 2,324 1/3 innings, 2,396 strikeouts, 49 bWAR

Brought to make his major league debut at just 19 years old, Sandy Koufax worked as a long reliever and a spot starter for his first three seasons with the major leagues, finally earning a rotation spot as the team headed West in 1958.

Interestingly, Koufax never had a full season under a 3.50 ERA until 1962, a season that he pitched less than 200 innings. He then went on one of the greatest four-year runs in the history of the game, and that run will have many people saying that Koufax should be much higher on this list.

Koufax went from a guy with one of the best curveballs in the game to discussions about him being the best left-handed pitcher that had ever gripped a baseball in less time than it takes a person to complete college.

From 1963-1966, Koufax averaged 24 wins, a 1.86 ERA, 0.91 WHIP, 298 innings, and 307 strikeouts. That was his average performance. One more time, because it may not have set in – THAT WAS HIS average SEASON.

Certainly, that run earns Koufax this spot on the best left-handed pitchers list, but his lack of depth makes it difficult to put him any higher. Over his career, Koufax was selected to 7 All-Star games, won 3 Cy Young Awards, and won the 1963 NL MVP. He also won the NL triple crown in 1963, 1965, and 1966.

Koufax was elected to the Hall of Fame in 1972 with 86.9% of the vote.

Next: 7. Kid K

7. Clayton Kershaw, 145 wins, 160 ERA+, 1,984 innings, 2,173 strikeouts, 62 bWAR

Many will be surprised to see Kershaw ahead of Koufax, but when you break it down, it’s simply where it should be. Kershaw’s been arguably as elite in his best seasons and for a longer dominant stretch than Koufax, even if he’s never the same again as he’s been in the past due to the injuries currently keeping him out.

Kershaw was the 7th overall selection in the 2006 draft, and he moved quickly, making his major league debut just a couple months past his 20th birthday in 2008. That 2008 season remains the only season of his career that Kershaw completed with an ERA over 3, even if he had an injury.

Of the 100 best left-handed pitchers by bWAR, Kershaw is first by a long shot in ERA+, which shows just how much more dominant he’s been than any other pitcher out there. He’s also 3rd all-time in strikeout percentage.

The remarkable thing with Kershaw is that he has been so incredibly elite in all aspects of pitching – not just at striking batters out (led the league 3 times), not just in preventing runs (led league in ERA 5 times), not just in endurance (led in innings once and complete games twice), and not just in victories (led league 3 times). He’s done it all.

Right now, it would be hard to make the argument against Kershaw entering the Hall of Fame, even if he never took the mound again, but that’s something for another article!

Over his 11 seasons, Kershaw has been selected for 7 All-Star games, won 3 Cy Youngs and received votes in 4 other years, won the 2014 NL MVP and received votes 5 other seasons, won a Gold Glove, won the 2011 National League pitching triple crown, and his work off the field has led to him winning the Roberto Clemente award. He’s a gem that we should all be enjoying while we have the opportunity!

Next: 6. Big Ruby

6. Rube Waddell, 193 wins, 135 ERA+, 2,961 1/3 innings, 2,316 strikeouts, 60.8 bWAR

He stood 6’1″ tall and weighed in at nearly 200 pounds. At the turn of the 20th century, that was a giant of a man, and to come from the left side with that size was nearly unfair. Such was the reputation of George Edward Waddell, known as Big Ruby or, more commonly, Rube.

Waddell made his major league debut at age 20, but he would not return to the big leagues until 2 seasons later in 1899, making an impressive debut with Louisville. A year later, he won the ERA title in the National League for Pittsburgh.

A rare well-traveled ballplayer, Waddell would be traded to the Cubs in 1901, then find his way to the Philadelphia Athletics. It was with the Athletics that Rube would establish himself among the best left-handed pitchers that have ever toed the rubber.

Waddell’s 1904-1905 seasons were ridiculously good. He tossed 711 2/3 innings with a 1.56 ERA and 66 complete games over that time. He wasn’t just an era-typical control specialist, working to create contact. Waddell struck out over 23% of hitters in those two seasons in an era where striking out even 15% was nearly unheard of.

That incredible usage had a toll, though, and Waddell was not able to take the mound again due to pain after age 33, but he had already made his impact by that point as one of the best left-handed pitchers in the game’s infancy, if not onde of the best pitchers in the game, regardless of handedness.

Waddell was elected to the Hall of Fame in 1946 by the Old Timers Committee.

Next: 5. Gettysburg Eddie

5. Eddie Plank, 326 wins, 122 ERA+, 4,495 2/3 IP, 2,246 strikeouts, 91.5 bWAR

Joining Waddell in that 1946 class was the guy who took over the mantle from him as the best left-handed pitcher in the game right away in his rookie year with the same A’s team that Waddell had starred for, and then he ran with that title for many seasons, finally jumping ship to the Federal League after a contract dispute, and returning, still dominant at 40 years old to the St. Louis Browns before walking away after posting a 1.79 ERA over 131 innings at 41.

Unlike Waddell, who was a power pitcher, Plank was known for his ability to keep hitters off balance and to pound the strike zone, walking just 6% of hitters over his career. Plank would work with meticulous precision in his routine on the mound, even talking with himself at times, often frightening other players who were curious of Plank’s mental stability.

Plank set the standard for lefty victories that would remain until Warren Spahn passed him, but he still remains the best left-handed pitcher all-time in shutouts with 69, pitching to an incredible 2.35 career ERA over almost 4,500 innings. However his quirks on the mound were such that when he began to complain about his contract, the Athletics were more than willing to let him walk.

Plank had a brilliant season at 40 years old with the St. Louis Terriers, but the league folded after the 1915 season, leaving Plank once again in turmoil about the future of his career. His former Terriers owner purchased control of the St. Louis Browns and brought Plank with him. Complaining of stomach issues that were overwhelming his ability to pitch, Plank retired after the 1917 season.

Plank passed away in 1926, 20 years before he would be immortalized by the Old Timers Committee.

Next: 4. Lefty

4. Steve Carlton, 329 wins, 115 ERA+, 5,217 2/3 innings, 4,136 strikeouts, 84.4 bWAR

A Miami boy, Carlton went from Miami-Dade College to the St. Louis Cardinals, yet another product of the incredible Cardinals scouting system in the era. Carlton was signed at 19, and he worked all the way to the MLB club in 1964, using his hard fastball and slider along with his impressive plane from his 6’4″ frame to generate plane on his pitches.

Carlton fought with the Cardinals about salary, and it eventually led to his exodus from St. Louis as he was traded after a 1970 holdout upset the Cardinals owner, even though the determined Carlton would go on to win 20 games in 1971 for the first time in his career.

After a trade to the Phillies, Carlton established himself immediately as the best left-handed pitcher in the game. He was so dominant immediately with the Phillies that he was able to win nearly half of the Phillies total team victories in his first season on the team (27 wins of the team’s 59).

Carlton would toil in Philadelphia on mediocre teams until the team started to really pick up at the end of the 1970s, eventually making the World Series in 1980 with Carlton at the front of the rotation. Overall, Carlton would sparkle in his career in the postseason, throwing 99 1/3 innings, striking out 84, with a 3.26 ERA.

For roughly two seasons in the early 1980s, Carlton was locked in a battle with Nolan Ryan over who would be the all-time leader in strikeouts. After both surpassed Walter Johnson in 1982, they went back and forth for two seasons before Ryan pulled away in 1985. Carlton remains 4th all-time in strikeouts and second among left-handed pitchers.

After injuries wreaked havoc on his 1985 season, Carlton struggled to open the 1986 season, but after being let go by the Phillies and Giants, he caught on with the White Sox and was able to post a 3.69 ERA over 10 starts. He was not able to replicate that success in 1987 with Cleveland or Minnesota, actually being left off the Twins postseason roster as they pushed toward the 1987 World Series. He’d come back for 4 more appearances with the Twins in 1988 that did not go well before being released and hanging things up for good.

Carlton was elected to 10 All-Star games, won 4 Cy Young awards and received votes in 2 more seasons, received MVP votes in 6 seasons, and won the 1981 NL Gold Glove. He also won the 1972 NL pitching triple crown.

He was elected to the Hall of Fame in 1994 with 95.6% of the vote.

Next: 3. Old Boss

3. Warren Spahn, 363 wins, 119 ERA+, 5,243 2/3 innings, 2,583 strikeouts, 92.6 bWAR

In the modern game, pitchers simply don’t win 400 games. Well, pitchers named Warren Spahn don’t win 400 games, that is. After making his major league debut in 1942, Spahn was whisked off to military service, missing all of the next three seasons and part of the 1946 season as he got back onto his game. With those three seasons in his early 20s back, it’s hard to believe that Spahn would not have had the 37 more wins to reach 400 wins.

While Spahn was not a guy who struck a ton of guys out, that does not mean that he ever pitched to contact. He wasn’t afraid to pitch around a bat or two in order to set up a hitter the way he wanted. Spahn was by no means a large man at 6′ tall and 175 pounds dripping wet, but he was intimidating on the mound in that he knew how to work around every batter to make him look foolish, and no hitter likes that.

Spah would haave preferred to play first base and slug long fly balls, but he didn’t have the contact ability to be a full-time hitter. His father had drilled into him the importance of a mechanically-sound delivery on the mound, and Spahn would later credit his high leg kick and long career both to his father as he was able to stay healthy and have deception on the mound while he did so.

None other than Casey Stengel managed Spahn in his first season and reportedly stated then that he could be one of the best left-handed pitchers in the league if he avoided injury. While many baseball players entertained troups from camps, well behind conflict lines during World War II, Spahn was on the front lines, taking bullets in the Battle of the Bulge, eventually earning a Bronze Star, a Purple Heart, a battlefield promotion, and a Presidential citation.

Spahn would remain incredibly humble about his service, often refusing to discuss himself as a hero and never allowing the discussion of how many more wins he “could have had” to come up, in contrast with many other players who served much less active roles. Instead, Spahn found his service gave him focus he didn’t have prevoiusly on the mound, allowing him to “read” hitters, attacking them with pitches they wer never expecting.

Over his career, Spahn was selected to 17 All-Star games and appeared on 15 MVP ballots, his best finish being in 1956, when he was 4th on the ballot. He won the 1957 Cy Young Award, when it was still one award for both leagues, and he was on 4 other ballots. The final award he won may have meant the most to him, however, as he won the 1961 Lou Gehrig Memorial Award. Growing up, Spahn adored Gehrig and wanted to be just like the Yankee first baseman.

Spahn was elected to the Hall of Fame in 1973.

Next: 2. Robert Moses

2. Lefty Grove, 300 wins, 148 ERA+, 3,940 1/3 innings, 2,266 strikeouts, 112.5 bWAR

Waddell, Plank, and then Grove. The Athletics were able to lay claim to arguably the three best left-handed pitchers to hold the title in the game’s history, and Grove grabbed those reigns quickly, debuting with the A’s a decade after Plank left the team, and in his second season winning the ERA title in the American League.

Not a guy who struck out a ton of hitters, Grove was a player that no one seemed to be able to square up. Even in the offensive explosion of the 1920s and 1930s, Grove allowed just 162 home runs, or to put in better perspective, for every 103 hitters that came to the plate to face Grove, one would hit a home run. For comparison, the lowest HR/9 of any qualified left-handed starter in 2017 was Giants lefty Ty Blach, who allowed a home run for every 41 hitters he faced, and that was on a top season for Blach versus Grove’s career rate, even during an era when home runs were flying out due to a shift in the ball’s manufacturing.

As was the case with many of the Athletics best players for the first half of the 20th century, contract squabbles led to a departure between player and team, and for Grove, it meant a trade to Boston, where he was frequently the best thing on a bad Red Sox team throughout his career.

The downfall of his second half of his career being played with the Red Sox in the state they were in was that Grove didn’t get another chance to pitch in the postseason. He excelled in his appearances in postseason baseball with the Athletics, pitching to a 1.75 ERA over 51 1/3 postseason innings, never allowing a postseason home run, and posting a 6/36 BB/K ratio.

Though the game started midway through his career, Grove was still selected to 6 All-Star games. He won the 1931 MVP award and received votes in 7 other seasons. He won the AL pitching triple crown in 1930 and 1931, the first lefty to ever win multiple triple crowns.

Grove was elected to the Hall of Fame in 1947.

Next: 1. Big Unit

1. Randy Johnson, 303 wins, 135 ERA+, 4,135 1/3 innings, 4,875 strikeouts, 103.6 bWAR

Scouts often use the phrase “all arms and legs”. Randall David Johnson seemed to have nothing but arms and legs, and they were always moving in a very, VERY violent manner toward the unfortunate hitter who was in the batter’s box against him.

Incredibly, with all the innings he tossed, Johnson still factors as the #2 left-handed pitcher in strikeout rate, which is a testament to just how great he truly was, not just one of the best left-handed pitchers of all-time, but definitely among the handful of the best pitchers in the game’s history, regardless of handedness.

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After a very good career with the University of Southern California, Johnson was a 2nd round pick of the Montreal Expos, but his incredible velocity had difficulty finding the plate, and the Expos made him part of a package of players they sent to the Seattle Mariners for fellow lefty Mark Langston, one of the best left-handed pitchers not on this list.

The Mariners were willing to live with the wildness to get the incredible combination of velocity and break on Johnson’s sweeping slider from Randy’s 6’10” long-limbed frame, which was nearly unhittable by batters as long as Johnson put the ball over the plate. Predictably, Big Unit led the league in walks in his first three years in the Mariners rotation, but as he began to figure out his control, he really figured it out.

In his final full season with the Mariners, 1997, Johnson walked 77 and struck out 291 hitters. In 1991, he had struck out nearly 70 less while walking nearly 70 more!

The Mariners traded Johnson in 1998, and he had a dominant finish to the season for the Houston Astros before signing with the Arizona Diamondbacks, where he would have one of the more legendary postseasons in recent memory in 2001. Johnson went undefeated in the NLCS and World Series in 5 appearances, 4 of them starts. He threw 33 1/3 innings, struck out 38 hitters, and walked just 6. He was selected as the World Series MVP as his Diamondbacks overcame a dynastical Yankee team to win.

Johnson would keep slinging the ball until he was 45, still striking out hitters at a dominating rate to his very end. He finished with 10 All-Star games, 5 Cy Young Awards, 10 Cy Young voting appearances, 9 times he received votes for MVP, and he won the 2002 pitching triple crown in the National League.

He was elected to the Hall of Fame in 2015 on the first ballot with 97.3% of the vote.

Next: Top Ten Negro League Players

That is our view on the 20 best left-handed pitchers in MLB history. Who is too high? Who is too low? Who is omitted altogether? Tell us in the comments!