Baseball Reference Blog
Top 8 Players with Most Cy Young Awards Won
Posted by Darren Baker on April 10, 2024
The Cy Young Award is given to the top pitcher in each league annually. Why call it the Cy Young? Well, this legendary hurler posted 22 seasons in MLB before World War I even started. He is the all-time leader in wins (511), games started (815), innings (7,356), and is third all-time in WAR (163.6). There were also those 14 consecutive 20-win seasons, five of them 30+. The point is that this award is well named for this luminary during the silent film era.
Since this award started in 1956, 22 pitchers have won it more than once. A deeper plunge shows only 11 men have won it at least three times. That’s who this list will focus on, with the exception of the three current players who have won the award three times (Clayton Kershaw, Max Scherzer, and Justin Verlander). For the sake of posterity, here are the eight pitchers with at least three Cy Young Awards.
Sandy Koufax
Position: Pitcher
Bats: Right • Throws: Left
6-2, 210lb (188cm, 95kg)
Born: December 30, 1935 (Age: 88-062d) in Brooklyn, NY us
High School: Lafayette HS (Brooklyn, NY)
Schools: Columbia University (New York, NY), University of Cincinnati (Cincinnati, OH)
Debut:
June 24, 1955
(Age 19-176d,
11,268th in major league history)
vs. MLN 2.0 IP, 1 H, 2 SO, 1 BB, 0 ER
Last Game:
October 2, 1966
(Age 30-276d)
vs. PHI 9.0 IP, 7 H, 10 SO, 1 BB, 2 ER, W
Hall of Fame: Inducted as Player in 1972.
(Voted by BBWAA on 344/396 ballots)
View Sandy Koufax’s Page at the Baseball Hall of Fame (plaque, photos, videos).
Rookie Status: Exceeded rookie limits during 1956 season
Full Name: Sanford Koufax
Nicknames: The Left Arm of God
Pronunciation: \KOE-facks\
View Player Info from the B-R Bullpen
View Player Bio from the SABR BioProject
Career
48.9
165
87
2.76
397
314
9
2324.1
2396
1.106
Unfathomably, this lefty legend retired at the age of 30: Sandy Koufax. Debuting at age 19 in 1955 for the Brooklyn Dodgers, Koufax had a very pedestrian first several seasons. In fact, he never had more than 11 wins, an ERA lower than 3.20, or a WHIP below 1.331. Then in 1961, once he was adjusted to Los Angeles, he had a meteoric last six years. He won Cy Youngs in 1963, 1965, and 1966 with win totals of 25, 26, and 27; three times he had more than 300 innings in a season. During his last five seasons, his ERA numbers were off the charts: 2.54, 1.88, 1.74, 2.04, and 1.73; his WHIP never was higher than .092 in that stretch. In 1963, he doubled as the NL MVP, and he helped lead the Dodgers to four World Series titles in his career. To this day, his 382 K’s in 1965 is the second highest total since the 1800s. There are a ton more of his sparkling stats that could be listed, but this isn’t a Koufax biography. Due to chronic elbow soreness, Sandy Koufax retired after the 1966 season, but this Dodger great has a plaque in Cooperstown, and he collected three Cy Young Awards along the way.
Jim Palmer
Position: Pitcher
Bats: Right • Throws: Right
6-3, 190lb (190cm, 86kg)
Born: October 15, 1945 (Age: 78-138d) in New York, NY us
High School: Scottsdale HS (Scottsdale, AZ)
Schools: Arizona State University (Tempe, AZ), Towson University (Towson, MD)
Debut:
April 17, 1965
(Age 19-184d,
12,341st in major league history)
vs. BOS 2.0 IP, 1 H, 1 SO, 2 BB, 0 ER
Last Game:
May 12, 1984
(Age 38-210d)
vs. OAK 2.0 IP, 5 H, 1 SO, 1 BB, 4 ER
Hall of Fame: Inducted as Player in 1990.
(Voted by BBWAA on 411/444 ballots)
View Jim Palmer’s Page at the Baseball Hall of Fame (plaque, photos, videos).
Rookie Status: Exceeded rookie limits during 1965 season
Agents: Ed Keating • Previously: Ron Shapiro?
Full Name: James Alvin Palmer
Nicknames: Cakes
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Career
68.5
268
152
2.86
558
521
4
3948.0
2212
1.180
Like Koufax, Jim Palmer debuted in the big leagues at age 19. From 1965 to 1984, Palmer was a stalwart on the hill for the Baltimore Orioles. Definitely the golden era of Oriole baseball, in addition to Jim’s three Cy Young Awards in the 1970s, he was a three-time World Champion who helped the O’s to 8 playoff appearances. He threw at least 208 innings in a season 11 times; think about that in today’s pitch-count controlled game. Seven times he had 20 wins or more. His three Cy Youngs came in 1973, 1975, and 1976 with ERA titles in ‘73 (2.40) and ‘75 (2.09). This former Jockey underwear spokesperson was never a huge strikeout guy, but he was a reliable innings-eater for some great teams in Baltimore, and he collected four Gold Gloves in his time as well. Jim Palmer’s days on the mound got him into the Hall of Fame, and those three Cy Young Awards are among the most in MLB history.
Tom Seaver
Position: Pitcher
Bats: Right • Throws: Right
6-1, 195lb (185cm, 88kg)
Born: November 17, 1944 in Fresno, CA us
Died: August 31, 2020 (Aged 75-288d) in Calistoga, CA
Draft: Drafted by the Los Angeles Dodgers in the 10th round of the 1965 MLB June Amateur Draft from University of Southern California (Los Angeles, CA) and the Atlanta Braves in the 1st round (20th) of the 1966 MLB January Draft-Secondary Phase from University of Southern California (Los Angeles, CA).
High School: Fresno HS (Fresno, CA)
Schools: Fresno City College (Fresno, CA), University of Southern California (Los Angeles, CA)
Debut:
April 13, 1967
(Age 22-147d,
12,556th in major league history)
vs. PIT 5.1 IP, 6 H, 8 SO, 4 BB, 2 ER
Last Game:
September 19, 1986
(Age 41-306d)
vs. TOR 4.0 IP, 5 H, 1 SO, 2 BB, 3 ER, L
Hall of Fame: Inducted as Player in 1992.
(Voted by BBWAA on 425/430 ballots)
View Tom Seaver’s Page at the Baseball Hall of Fame (plaque, photos, videos).
Rookie Status: Exceeded rookie limits during 1967 season
Agents: Bob Lawrence
Full Name: George Thomas Seaver
Nicknames: Tom Terrific or The Franchise
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Career
109.9
311
205
2.86
656
647
1
4783.0
3640
1.121
From the late 60s to the late 70s, Tom Seaver was the New York Mets, as he was often called The Franchise. He was a part of the Miracle Mets winning it all in 1969 and the improbable 1973 NL Pennant winners. This three-time Cy Young winner (1969, 1973, and 1975) was a strikeout machine in Queens. He still sits sixth on the all-time K’s list (3,640). Tom Terrific threw at least 213 innings in his first 13 big-league seasons. For the ‘69 season, he had 25 wins, 2.21 ERA, and 208 strikeouts to secure his first Cy Young. He followed that up with seasons of 283 and 289 K’s; five times he led the National League in punched tickets. As a pitcher, he led the league in WAR three times. In 1977, he emotionally got sent to Cincinnati in one of MLB’s first notable mid-season trade deals. Undeterred, he went 14-3 the rest of that year for the Big Red Machine. Seaver memorably got his 300th career win at Yankee Stadium as a Chicago White Sox in 1985. This true ace and durable workhorse is 18th on the career wins list, and he was inducted in the Hall of Fame in 1992. With a stellar 20-season run in baseball and three Cy Young Awards, Tom Seaver will be remembered as one of the all-time pitching greats.
Pedro Martínez
Position: Pitcher
Bats: Right • Throws: Right
5-11, 170lb (180cm, 77kg)
Born: October 25, 1971 (Age: 52-128d) in Manoguayabo, Dominican Republic do
Debut:
September 24, 1992
(Age 20-335d,
16,246th in major league history)
vs. CIN 2.0 IP, 2 H, 1 SO, 1 BB, 0 ER
Last Game:
September 30, 2009
(Age 37-340d)
vs. HOU 4.0 IP, 6 H, 2 SO, 1 BB, 3 ER
Hall of Fame: Inducted as Player in 2015.
(Voted by BBWAA on 500/549 ballots)
View Pedro Martínez’s Page at the Baseball Hall of Fame (plaque, photos, videos).
Rookie Status: Exceeded rookie limits during 1993 season
Agents: Fernando Cuza, Bob Gilhooley
Full Name: Pedro Jaime Martínez
Nicknames: Pedro el Grande or Petey
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Relatives: Brother of Ramón Martínez; Cousin of Denny Bautista
Career
83.9
219
100
2.93
476
409
3
2827.1
3154
1.054
There have been few pitchers in MLB history with as much flair and electricity as Pedro Martinez. This three-time Cy Young Award winner (1997, 1999, and 2000) only stood 5’11 and was 170 pounds, but he could bring it; just ask Don Zimmer and Karim Garcia. Petey started as an LA Dodger before moving north of the border to the Montreal Expos. He broke out in 1997 with his first Cy Young; he led the NL in several categories: ERA (1.90), complete games (13), ERA+ (219), FIP (2.39), and WHIP (.932). Then Pedro truly became a legend in Boston. As a Red Sox, he led the AL in ERA four times, K’s three times, and WAR two times. His back-to-back Cy Young wins in 1999 and 2000 were truly historic performances. In 1999, he struck out 313 batters and had a 13.2 K per nine average. That year in the All Star Game at Fenway, Martinez started for the American League and mowed down five men (three future Hall of Famers), winning the All-Star MVP Award. The following season, Pedro repeated his dominance and led the AL in 11 pitching categories. Yes, there was the “who’s your daddy” fiasco at Yankee Stadium in the 2003 ALCS, but the fiery Dominican helped the Red Sox break the curse in 2004. He also had a memorable relief appearance to close out Cleveland in the 1999 ALDS. Pedro Martinez was a dynamic showstopper, and his three Cy Young Awards are among the most ever.
Steve Carlton
Position: Pitcher
Bats: Left • Throws: Left
6-4, 210lb (193cm, 95kg)
Born: December 22, 1944 (Age: 79-070d) in Miami, FL us
High School: North Miami HS (North Miami, FL)
School: Miami Dade College, North Campus (Miami, FL)
Debut:
April 12, 1965
(Age 20-111d,
12,325th in major league history)
vs. CHC 0.0 IP, 0 H, 0 SO, 1 BB, 0 ER
Last Game:
April 23, 1988
(Age 43-123d)
vs. CLE 5.0 IP, 9 H, 4 SO, 3 BB, 8 ER, L
Hall of Fame: Inducted as Player in 1994.
(Voted by BBWAA on 436/456 ballots)
View Steve Carlton’s Page at the Baseball Hall of Fame (plaque, photos, videos).
Rookie Status: Exceeded rookie limits during 1966 season
Agents: Dick Moss • Previously: David Landfield, LaRue Harcourt
Full Name: Steven Norman Carlton
Nicknames: Lefty
View Player Info from the B-R Bullpen
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Career
90.2
329
244
3.22
741
709
2
5217.2
4136
1.247
All you have to say is Lefty in Philadelphia; everyone knows #32 emblazoned against the backdrop of Citizens Bank Park. Steve Carlton is an iconic Philadelphia Phillie and leads the franchise in wins and strikeouts; if not for other franchise legends, Grover Alexander and Robin Roberts, Lefty would lead in more categories. Carlton was the first pitcher ever to win four Cy Young Awards (1972, 1977, 1980, and 1982). He was acquired by the Phils prior to the 1972 season from St. Louis for fan-favorite Rick Wise. Quickly, Carlton introduced himself to the City of Brotherly Love with an epic 1972 season and his first Cy Young. He won an astounding 27 games for a team that only won 59 overall; that year he also topped the NL in ERA (1.97), games started (41), innings pitched (346), strikeouts (310), and FIP (2.01). Lefty led the NL in K’s five times and is still fourth on the all-time list (4,136). He threw at least 229 innings 16 times and had five 20-win seasons. Winning the first World Series in franchise history, a nearly 100-year wait, will always make Lefty immortal in Philadelphia. Those four Cy Young Awards still rank Steve Carlton near the top in MLB history.
Greg Maddux
Position: Pitcher
Bats: Right • Throws: Right
6-0, 170lb (183cm, 77kg)
Born: April 14, 1966 (Age: 57-322d) in San Angelo, TX us
Draft: Drafted by the Chicago Cubs in the 2nd round of the 1984 MLB June Amateur Draft from Valley HS (Las Vegas, NV).
High School: Valley HS (Las Vegas, NV)
Debut:
September 2, 1986
(Age 20-141d,
15,224th in major league history)
vs. HOU 1.0 IP, 1 H, 1 SO, 0 BB, 1 ER, L
*
(*game was a suspended game and the player actually debuted the day following the day listed.)
Last Game:
September 27, 2008
(Age 42-166d)
vs. SFG 6.0 IP, 2 H, 2 SO, 0 BB, 1 ER, W
Hall of Fame: Inducted as Player in 2014.
(Voted by BBWAA on 555/571 ballots)
View Greg Maddux’s Page at the Baseball Hall of Fame (plaque, photos, videos).
Rookie Status: Exceeded rookie limits during 1987 season
Agents: Boras Corporation
Full Name: Gregory Alan Maddux
Nicknames: Mad Dog or The Professor
Pronunciation: \MADD-ucks\
View Player Info from the B-R Bullpen
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Relatives: Brother of Mike Maddux
Career
106.6
355
227
3.16
744
740
0
5008.1
3371
1.143
The Atlanta Braves won 14 consecutive division titles from the early 90s to the mid 2000s, and Greg Maddux was a major factor in that dominant run. His four consecutive Cy Young Awards from 1992-1995 have only been matched by one other, a tall pitcher yet to be named. Not overpowering but more knifing as a pitcher, Mad Dog five times led the NL in innings pitched and won four ERA titles; his season lows were 1.56 in ‘94 and 1.63 in ‘95. 1995 is also the year the Braves finally broke through and won the World Series. Greg’s remarkable durability and consistency were hallmarks during his prestigious career; he started over 30 games 19 out of 23 big league seasons, and he won at least 15 games in 17 consecutive years. In his 1994 Cy Young campaign, he posted the 11th best single-season WHIP (.811) ever. His cerebral style collected him 355 wins and 3,371 K’s, good enough for 9th and 10th all time respectively. You can’t tell the story of modern baseball history without Greg Maddux, and his four Cy Youngs are constant reminders of how phenomenal he was on the bump.
Randy Johnson
Position: Pitcher
Bats: Right • Throws: Left
6-10, 225lb (208cm, 102kg)
Born: September 10, 1963 (Age: 60-173d) in Walnut Creek, CA us
Draft: Drafted by the Atlanta Braves in the 4th round of the 1982 MLB June Amateur Draft from Livermore HS (Livermore, CA) and the Montreal Expos in the 2nd round of the 1985 MLB June Amateur Draft from University of Southern California (Los Angeles, CA).
High School: Livermore HS (Livermore, CA)
School: University of Southern California (Los Angeles, CA)
Debut:
September 15, 1988
(Age 25-005d,
15,564th in major league history)
vs. PIT 5.0 IP, 6 H, 5 SO, 3 BB, 2 ER, W
Last Game:
October 4, 2009
(Age 46-024d)
vs. SDP 1.0 IP, 1 H, 2 SO, 0 BB, 0 ER
Hall of Fame: Inducted as Player in 2015.
(Voted by BBWAA on 534/549 ballots)
View Randy Johnson’s Page at the Baseball Hall of Fame (plaque, photos, videos).
Rookie Status: Exceeded rookie limits during 1989 season
Agents: Alan Nero, Barry Meister
Full Name: Randall David Johnson
Nicknames: Big Unit
View Player Info from the B-R Bullpen
View Player Bio from the SABR BioProject
Career
101.1
303
166
3.29
618
603
2
4135.1
4875
1.171
Not only is Randy Johnson one of the tallest players in MLB history at 6’10, but he has one of the tallest pitching resumes as well. There have been few men more intimidating on the mound as the Big Unit, as John Kruk can attest. Johnson won five Cy Young Awards, including four straight from 1999-2002. He is second to only Nolan Ryan on the all-time strikeout list (nine times leading the league); he had five 300-K seasons. He helped save baseball in Seattle when the Mariners charged back to win the AL West in 1995. Maybe one of the greatest trade-deadline acquisitions ever in 1998 by going 10-1 with a 1.28 ERA for the Astros? Who can forget his clutch performances in the 2001 World Series (both as a starter and reliever) when he won the co-MVP with Curt Schilling? How about his two no-hitters with the latter being a perfect game? He even hit a bird throwing a pitch in a spring training game. Oh, and this man regularly hit triple digits on the gun. The accolades and stats are Mount Rushmore-worthy: 303 wins, 4,875 K’s, five-time ERA champion, ten-time All-Star, Cy-Young winner in both leagues, and a very well deserving first-ballot Hall of Famer. Randy Johnson’s five Cy Young Awards are the second most in history, and that undoubtedly qualifies as one of baseball’s legendary pitchers.
Roger Clemens
Position: Pitcher
Bats: Right • Throws: Right
6-4, 205lb (193cm, 92kg)
Born: August 4, 1962 (Age: 61-210d) in Dayton, OH us
Draft: Drafted by the New York Mets in the 12th round of the 1981 MLB June Amateur Draft from San Jacinto College (Pasadena, TX) and the Boston Red Sox in the 1st round (19th) of the 1983 MLB June Amateur Draft from University of Texas at Austin (Austin, TX).
High School: Spring Woods HS (Houston, TX)
Schools: San Jacinto College (Pasadena, TX), San Jacinto College, North Campus (Houston, TX), University of Texas at Austin (Austin, TX)
Debut:
May 15, 1984
(Age 21-285d,
14,896th in major league history)
vs. CLE 5.2 IP, 11 H, 4 SO, 3 BB, 4 ER
Last Game:
September 16, 2007
(Age 45-043d)
vs. BOS 6.0 IP, 2 H, 4 SO, 3 BB, 0 ER
Rookie Status: Exceeded rookie limits during 1984 season
Agents: Randy Hendricks, Alan Hendricks
National Team: us USA (WBC)
Full Name: William Roger Clemens
Nicknames: Rocket or The Texas Con Man
View Player Info from the B-R Bullpen
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Relatives: Father of Kody Clemens
Career
139.2
354
184
3.12
709
707
0
4916.2
4672
1.173
The Rocket has the most career Cy Young Awards (7) in MLB history: 1986, 1987, 1991, 1997, 1998, 2001, and 2004. That’s dominance with four different teams, over three decades, and in two leagues. Roger Clemens was the prototypical power pitcher: a fireballer and scary figure from 60 feet and six inches away, and he made a memorable cameo in Kingpin playing up that image. This sturdy Texan broke out with the Boston Red Sox in 1986; that year he won his first Cy Young and was also the AL MVP with a 24-4 record, and he led the league in multiple categories: ERA (2.48), WHIP (.969), and FIP (2.81). Roger also got the Sox to literally an out of winning that elusive World Series title. He repeated as the Cy Young winner the next year with eye-popping 18 complete games and seven shutouts. During his time in Boston, Clemens also added a third Cy Young, some more ERA crowns, and two 20-strikeout games (still a nine-inning record). When the Rocket moved north to Toronto in 1997, he added two more Cy Young Awards and two more ERA titles (2.05 and 2.65) in his only seasons as a Blue Jay. Then Clemens moved to the Bronx and helped the Yankees to two more World championships, and he helped himself to another Cy Young in 2001 with a 20-3 mark, 213 K’s, and over 220 innings. He also offered Mike Piazza some shard pine in the 2000 Fall Classic. The last stop on the Tour de Roger was in his home state as a Houston Astro. There he added his last Cy Young in 2004 and helped rocket Houston to the World Series the following season. The Rocket’s career statline is as impressive as almost any hurler: 354 wins (9th all time), 4,672 strikeouts (3rd all time), 138.7 WAR (3rd all time for pitchers), two pitching Triple Crowns, and 11 All-Star selections. Roger Clemens has the most career Cy Young Awards, which earns him a solid spot on the list of MLB’s greatest pitchers ever.
The Cy Young Award is the yearly honor given to the top pitcher in each league. This award is voted on by members of the Baseball Writers’ Association of America. It was first awarded in 1956. From 1956 to 1966, it was only given to the top pitcher in MLB. Since 1967, it has been given to the top pitcher in the American League and the National League.
Roger Clemens has won the most Cy Young Awards (7). He won three with the Boston Red Sox (1986, 1987, and 1991), two with the Toronto Blue Jays (1997 and 1998), one with the New York Yankees (2001), and one with the Houston Astros (2004).
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