Most Cy Young Award Wins of All Time

These pitchers have won the Cy Young Award more times than any other players in MLB history.

For the last 66 years, the greatest pitchers in Major League Baseball have been honored annually with the Cy Young Award — arguably the most well-known individual award in all of sports.

It’s the type of award that becomes almost your entire identity once you get one. For the rest of your life, everywhere you go, that’s how you’re introduced: “Cy Young Award winner…”

So, we’ve established winning one Cy Young Award would equal a great career by any stretch of the imagination. But what about winning two? Or five? Or seven? That’s almost transcending greatness to some ethereal pitching realm relegated to only a very lucky few.

Let’s go there right now. Here’s a look at the pitchers with the most Cy Young Awards in MLB history.

5. Justin Verlander (Tie)

David J. Phillip / AP Photo

Born: Feb. 20, 1983 (Manakin-Sabot, Virginia)

Throws: Right

Career: Detroit Tigers (2005-17), Houston Astros (2017-present)

Cy Young Awards (3): 2011, 2019, 2022

Career highlights: Two-time World Series champion (2017, 2022), American League MVP (2011), ALCS MVP (2017), Triple Crown winner (2011), American League Rookie of the Year (2006), American League Comeback Player of the Year (2022)

Bottom line: This list starts off with a seven-way tie between those pitchers who have won a total of three Cy Young Awards. And we’re starting with Justin Verlander, whose late-career resurgence has been truly something to behold as he won his second World Series championship with the Houston Astros and his third Cy Young Award in 2022 at 39 years old. (It was also the same year he won American League Comeback Player of the Year.)

Verlander has as many no-hitters as he does Cy Young Awards, and in another era of four-man rotations, he would have cruised past the 300-win mark long ago. Verlander is a lock to be a first-ballot Hall of Famer when he finally ends his career.

5. Max Scherzer (Tie)

Washington Nationals Pitcher Max Scherzer

Nick Wass / AP Photo

Born: July 27, 1984 (Chesterfield, Missouri)

Throws: Right

Career: Arizona Diamondbacks (2008-09), Detroit Tigers (2010-14), Washington Nationals (2015-21), Los Angeles Dodgers (2021), New York Mets (2022-present)

Cy Young Awards (3): 2013, 2016, 2017

Career highlights: World Series champion (2019), eight-time MLB All-Star (2013-19, 2021)

Bottom line: Max Scherzer not only has three Cy Young Awards, he also has two career no-hitters and holds the MLB record with 20 strikeouts in a nine-inning game alongside Roger Clemens and Kerry Wood.

Scherzer has led the league in wins four times and strikeouts three times along with winning a World Series with the Washington Nationals in 2019. He’s also the youngest pitcher to defeat all 30 MLB teams and the fifth pitcher in history to start the All-Star Game for both the National League and American League.

5. Clayton Kershaw (Tie)

Los Angeles Dodgers Pitcher Clayton Kershaw

Alex Gallardo / AP Photo

Born: March 19, 1988 (Dallas, Texas)

Throws: Left

Career: Los Angeles Dodgers (2008-22)

Cy Young Awards (3): 2011, 2013, 2014

Career highlights: World Series champion (2020), National League MVP (2014), nine-time MLB All-Star (2011-17, 2019, 2022), Triple Crown winner (2011), Gold Glove Award winner (2011), Roberto Clemente Award (2012)

Bottom line: Clayton Kershaw went from being a prep phenom at Highland Park High in Dallas, Texas, to a star pitcher for the Los Angeles Dodgers, where he’s not only won three Cy Young Awards but also helped lead his team to the World Series championship in 2020. We believe he can count himself among the greatest pitchers of all time.

Kershaw won the National League MVP Award in 2014 — the same year he pitched his only career no-hitter — and has banked an amazing $268.3 million in career earnings through the end of the 2022 season.

5. Pedro Martinez (Tie)

Jim Rogash / AP Photo

Born: Oct. 25, 1971 (Manoguayabo, Dominican Republic)

Throws: Right

Career: Los Angeles Dodgers (1992-93), Montreal Expos (1994-97), Boston Red Sox (1998-2004), New York Mets (2005-08), Philadelphia Phillies (2009)

Cy Young Awards (3): 1997, 1999, 2000

Career highlights: World Series champion (2004), eight-time MLB All-Star (1996-2000, 2002, 2005, 2006), Triple Crown winner (1999)

Bottom line: Pedro Martinez became just the second player from the Dominican Republic to be enshrined in the Baseball Hall of Fame in 2015, following Juan Marichal, and he made it in his first year of eligibility.

Martinez had the greatest stretch of his career from 1997 to 2003 when he won all three of his Cy Young Awards and became one of just a handful of pitchers to win the award in both the National League and the American League. His greatest season came in 1999 when he was runner-up for the American League MVP after he went 23-4 with a 2.07 ERA and 313 strikeouts. But his greatest accomplishment came after his career had peaked, and he helped lead the Boston Red Sox to a World Series title in 2004, ending an 86-year drought.

5. Jim Palmer (Tie)

AP Photo

Born: Oct. 15, 1945 (New York, New York)

Throws: Right

Career: Baltimore Orioles (1965-84)

Cy Young Awards (3): 1973, 1975, 1976

Career highlights: Three-time World Series champion (1966, 1970, 1983), six-time All-Star (1970-72, 1975, 1977, 1978), four-time Gold Glove Award winner (1976-79)

Bottom line: One crazy fact about Jim Palmer is he played all 20 seasons of his MLB career with the same team, the Baltimore Orioles, and won a World Series championship in three different decades — 1966, 1970 and 1983. He’s also the only pitcher in MLB history to earn a World Series win in three different decades.

Palmer was just 20 years old in 1966 when he became the youngest pitcher in MLB history to toss a complete-game shutout in the World Series, which he did against legendary Los Angeles Dodgers pitcher Sandy Koufax. In all, the Orioles won six American League pennants with Palmer on the roster.

5. Tom Seaver (Tie)

AP Photo

Born: Nov. 17, 1944 (Fresno, California)

Died: Aug. 31, 2020, 75 years old (Calistoga, California)

Throws: Right

Career: New York Mets (1967-77, 1983), Cincinnati Reds (1977-82), Chicago White Sox (1984-86), Boston Red Sox (1986)

Cy Young Awards (3): 1969, 1973, 1975

Career highlights: World Series champion (1969), 12-time MLB All-Star (1967-73, 1975-78, 1981), National League Rookie of the Year (1967)

Bottom line: Tom Seaver became a household name with the New York Mets in the late 1960s, earning National League Rookie of the Year honors in 1967 and then winning an improbable World Series title in 1969.

Seaver led the National League in wins three times, ERA three times and strikeouts five times in his career — and the Mets renamed the address of Citi Field to 41 Seaver Way in 2019. Seaver died in August 2020 at 75 years old after suffering from Lewy body dementia.

5. Sandy Koufax (Tie)

James P. Kerlin / AP Photo

Born: Dec. 30, 1935 (Brooklyn, New York)

Throws: Left

Career: Brooklyn/Los Angeles Dodgers (1955-66)

Cy Young Awards (3): 1963, 1965, 1966

Career highlights: Four-time World Series champion (1955, 1959, 1963, 1965), National League MVP (1963), two-time World Series MVP (1963, 1965), three-time Triple Crown winner (1963, 1965, 1966), seven-time MLB All-Star (1961-66), MLB All-Century Team, MLB All-Time Team

Bottom line: Sandy Koufax owns arguably the most dominant five-year stretch of any pitcher in MLB history — from 1961 to 1966 he won three Cy Young Awards (when just one was given out), won the National League Triple Crown three times, won the World Series and World Series MVP twice, National League MVP once and pitched a perfect game on Sept. 9, 1965.

Koufax would win the World Series four times in his 11-year career and retired in 1966 at just 30 years old after suffering chronic pain in his left pitching elbow.

3. Greg Maddux (Tie)

John Bazemore / AP Photo

Born: April 14, 1966 (San Angelo, Texas)

Throws: Right

Career: Chicago Cubs (1986-92), Atlanta Braves (1993-2003), Chicago Cubs (2004-06), Los Angeles Dodgers (2006, 2008), San Diego Padres (2007-08)

Cy Young Awards (4): 1992-95

Career highlights: World Series champion (1995), eight-time MLB All-Star (1988, 1992, 1994-98), 18-time Gold Glove Award winner (1990-2002, 2004-08)

Bottom line: Greg Maddux won all four of his Cy Young Awards in consecutive seasons — the first with the Chicago Cubs in 1992 and the next three with the Atlanta Braves, including the final one in a year when his team won the World Series.

Only Maddux and fellow Hall of Famer Randy Johnson have won Cy Young Awards in four consecutive seasons. Maddux is probably the most consistent pitcher of all time as well as the best fielding pitcher. He set MLB records with 18 Gold Glove Awards and had 17 consecutive seasons with at least 15 wins.

3. Steve Carlton (Tie)

Philadelphia Phillies Pitcher Steve Carlton

Bill Ingraham / AP Photo

Born: Dec. 22, 1944 (Miami, Florida)

Throws: Left

Career: St. Louis Cardinals (1965-71), Philadelphia Phillies (1972-86), San Francisco Giants (1986), Chicago White Sox (1986), Cleveland Indians (1987), Minnesota Twins (1987-88)

Cy Young Awards (4): 1972, 1977, 1980, 1982

Career highlights: Two-time World Series champion (1967, 1980),10-time MLB All-Star (1968, 1969, 1971, 1972, 1974, 1977, 1979-82), Triple Crown (1972), Gold Glove Award (1981)

Bottom line: Steve Carlton played for an incredible 24 seasons in the majors — he remains the last pitcher in the National League to win 25 or more games in a single season and the last MLB pitcher to throw over 300 innings in a single season.

Carlton became the first pitcher in MLB history to win four Cy Young Awards in 1982 and also holds another pretty amazing record. Carlton’s distaste for reporters was such that he refused to grant an interview for the final 14 years of his career, from 1974 to 1988. That, my friends, is a record that will never be broken.

2. Randy Johnson

Arizona Diamondbacks Pitcher Randy Johnson

Roy Dabner / AP Photo

Born: Sept. 10, 1963 (Walnut Creek, California)

Throws: Left

Career: Montreal Expos (1988-89), Seattle Mariners (1989-98), Houston Astros (1998), Arizona Diamondbacks (1999-2004, 2007-08), New York Yankees (2005-06), San Francisco Giants (2009)

Cy Young Awards (5): 1995, 1999-2002

Career highlights: World Series champion (2001), World Series MVP (2001), 10-time MLB All-Star (1990, 1993-95, 1997, 1999-2002, 2004), Triple Crown (2002), MLB wins leader (2002), four-time ERA leader (1995. 1999, 2001, 2002), nine-time MLB strikeouts leader (1992-95, 1999-2002, 2004)

Bottom line: The abject fear batters felt stepping into the box to face 6-foot-10 pitcher Randy Johnson over his 22 seasons in the MLB is best defined by John Kruk’s comical reaction when Johnson threw a fastball over his head during the 1993 All-Star Game.

Johnson started his career with the Montreal Expos and won his first Cy Young Award with the Seattle Mariners in 1995. Johnson won his next four Cy Youngs with the Arizona Diamondbacks in four consecutive seasons from 1999 to 2002, including in 2001 when the Diamondbacks won the World Series and he was named World Series Most Valuable Player.

1. Roger Clemens

AP Photo

Born: Aug. 4, 1962 (Dayton, Ohio)

Throws: Right

Career: Boston Red Sox (1984-96), Toronto Blue Jays (1997-98), New York Yankees (1999-2003, 2007), Houston Astros (2004-06)

Cy Young Awards (7): 1986, 1987, 1991, 1997, 1998, 2001, 2004

Career highlights: American League MVP (1986), two-time Triple Crown winner (1997, 1998), MLB All-Century Team, two-time World Series champion (1999, 2000), 11-time MLB All-Star (1986, 1988, 1990-92, 1997, 1998, 2001, 2003-05)

Bottom line: Roger Clemens has more Cy Young Awards than any other player in MLB history. And he did it by winning them in three different decades, with three different teams and 18 years separating his first Cy Young in 1986 and final Cy Young in 2004.

That he almost certainly did it with a nice helping of modern science in the second half of his career is what has kept him out of the Hall of Fame — he’s the only 300-game winner not in Cooperstown because of his PED use.

It’s fair to point out Clemens was acquitted on six counts of lying to Congress during its hearings on steroids in baseball after a mistrial the first time around.