Greatest Cy Young Award Winners of All Time

The best pitchers to win the Cy Young Award really were more impressive in the good old days.

Where have all the great pitching performances gone? To the showers, presumably. In the era of pitch counts, five-and-fly starters and relievers aplenty, pitchers aren’t around long enough to put up gaudy numbers that make eyes bulge.

For proof, look no further than this list of greatest Cy Young Award (CYA) performances, which I ranked according to Wins Above Replacement (credit Baseball Reference with a save.) Of the top 30, only one took place since the 2009 season. Sorry, but you’ll have to read on to know the culprit. As for the others, well, enjoy them now. There will be $2 beers at the ballpark before you see their likes again.

30. Pat Hentgen (1996)

Gary Stewart / AP Photo

Team: Toronto Blue Jays

Season statistics: 20-10 record/265.2 innings pitched/3.22 earned run average

WAR: 8.6

Bottom line: Hentgen edged out Andy Pettitte (21-8, 3.87) for Cy Young Award honors, but if the runner-up hadn’t pitched with the New York Yankees, I doubt that the result would have been close. The right-hander led the league in fewest home runs allowed per nine innings (0.7) — no small feat in a season that produced a record number of long balls.

29. Randy Johnson (1995)

Duncan Livingston / AP Photo

Team: Seattle Mariners

Season statistics: 18-2/214.1/2.48

WAR: 8.6

Bottom line: Remarkably, Johnson rang up 232 of his 303 career wins and all five of his Cy Young Awards after he turned 30 years old. Hmmmmm. Why was the Big Unit rarely suspected to be a steroids cheater then? Could it be that he intimidated the Hall of Fame voters as much as the batters? Look, I don’t pretend to know the answers here, but there was good reason to ask more questions. This is why I was among 15 who took a pass in his first (and final) year on the ballot.

28. Johan Santana (2004)

Jeff Roberson / AP Photo

Team: Minnesota Twins

Season statistics: 20-6/228.0/2.61

WAR: 8.7

Bottom line: In the first (and best) of three consecutive stellar seasons, Santana led the league in earned run average, strikeouts and fewest hits per inning. Yeah, and “Oye Coma Va” was pretty good, too.

27. Roger Clemens (1986)

AP Photo

Team: Boston Red Sox

Season statistics: 24-4/254.0/2.48

WAR: 8.8

Bottom line: Clemens was lights out in the regular season — the league leader in wins and earned run average garnered all 24 first-place votes. A subpar postseason took some of the gloss off the first of his seven such (tainted) awards, though.

26. Bob Gibson (1970)

AP Photo

Team: St. Louis Cardinals

Season statistics: 23-7/294.0/3.12

WAR: 8.9

Bottom line: Gibson fell short of his ridiculous 1968 standards (more on that later), but the mighty righty did enough to beat out Gaylord Perry and Fergie Jenkins in a three-horse race. A .767 win percentage was the best of his career.

25. Vida Blue (1971)

AP Photo

Team: Oakland Athletics

Season statistics: 24-8/312.0/1.82

WAR: 9.0

Bottom line: In his first full season in the bigs, the 21-year-old lefty became the youngest player to win Cy Young and Most Valuable Player awards in the same season. Team owner Charles Finley just hated that he was this good. He was the tightwad who had to pay him.

24. Pedro Martinez (1997)

Mike Poche / AP Photo

Team: Montreal Expos

Season statistics: 17-8/241.1/1.90

WAR: 9.0

Bottom line: It’s difficult to tell which is more impressive — that Martinez had more complete games (13) than 24 teams or that his earned run average was nearly 231 percent better than the major league average (4.38).

23. Greg Maddux (1992)

John Swart / AP Photo

Team: Chicago Cubs

Season statistics: 20-11/268.0/2.18

WAR: 9.1

Bottom line: It’s hard to believe that Maddux was a 20-game winner only twice in his career. This was the first of two in a row. He beat out teammate Tom Glavine (20-8, 2.76) by a comfortable margin. Together, that was about 38 inches worth of strike zone by my count.

22. Randy Johnson (1999)

Roy Dabner / AP Photo

Team: Arizona Diamondbacks

Season statistics: 17-9/271.2/2.48

WAR: 9.1

Bottom line: While Houston Astros ace Mike Hampson (22-4) bolstered a more impressive record — he also had supersaver Billy Wagner, who finished fourth in the vote — Johnson was easily the most dominant pitcher in his league. The Big Unit was the leader in earned run average, innings pitched and strikeouts.

21. Dean Chance (1964)

AP Photo

Team: Los Angeles Angels

Season statistics: 20-9/278.1/1.65

WAR: 9.4

Bottom line: How drop-dead great was Chance this season? He had more wins, complete games and shutouts, plus a better earned average than that other pitcher in town. Yeah, that’s him — Sandy Koufax.

20. Roger Clemens (1987)

Jim Mone / AP Photo

Team: Boston Red Sox

Season statistics: 20-9/281.2/2.97

WAR: 9.4

Bottom line: Clemens outdid himself in the second of back-to-back Cy Young Award seasons. His 18 complete games (in 36 starts) remain the most in the bigs in the last 34 years. By comparison, the American League had 21 complete games in the 2021 season. Total.

19. Ron Guidry (1978)

Paul Burnett / AP Photo

Team: New York Yankees

Season statistics: 25-3/273.2/1.74

WAR: 9.6

Bottom line: The unanimous Cy Young Award winner deserved far more consideration for Most Valuable Player honors. He was second to Boston Red Sox slugger Jim Rice (7.6), despite a much higher WAR number.

18. Bret Saberhagen (1989)

Paul Sakuma / AP Photo

Team: Kansas City Royals

Season statistics: 23-6/262.1/2.16

WAR: 9.7

Bottom line: That Saberhagen finished ninth in the Most Valuable Player vote was incomprehensible. The right-hander accounted for one-quarter of the Royals win total. Somehow, he didn’t receive one stinkin’ first-place vote. Kinda makes you wonder if any of the 27 judges actually watched the games.

17. Greg Maddux (1995)

Jeff Roberson / AP Photo

Team: Atlanta Braves

Season statistics: 19-2/209.2/1.63

WAR: 9.8

Bottom line: Unless you were a Braves fan, you did not want to attend one of their road games when Maddux was scheduled to pitch. In 15 starts outside of Fulton County, the spoilsport had a 13-0 record and .178/.205/.231 slash line.

16. Pedro Martinez (1999)

Charles Krupa / AP Photo

Team: Boston Red Sox

Season statistics: 23-4/213.1/2.07

WAR: 9.8

Bottom line: We’ve often seen players win major awards in the regular season and then go pffft in the playoff, so that’s what made this performance so special. Martinez pitched 17 shutout innings in the postseason, which included a two-hit, seven-inning victory over the New York Yankees.

15. Jacob deGrom (2018)

Jeff Roberson / AP Photo

Team: New York Mets

Season statistics: 10-9 /217.0/1.70

WAR: 9.9

Bottom line: Here’s the only pitcher of the last decade-plus to make the list. And deGrom did it with 10 victories. Ten. Because starters aren’t around when many games are decided, that’s less of a consideration now. Some seamheads call it progress. I call it really, really weird.

14. Ferguson Jenkins (1971)

AP Photo

Team: Chicago Cubs

Season statistics: 24-13/325.0/2.77

WAR: 10.1

Bottom line: Would you believe that Jenkins was almost as productive at the plate, where he hit six homers and drove in 20 runs in 115 at-bats? Add his 1.6 0WAR, and he moves to No. 4 on this list.

13. Randy Johnson (2001)

Gene J. Puskar / AP Photo

Team: Arizona Diamondbacks

Season statistics: 21-6/249.2/2.49

WAR: 10.1

Bottom line: Johnson produced back-to-back seasons (2001-02) that ranked among the best ever. The Big Unit set what would be his career high in strikeouts (372) in this one.

12. Steve Carlton (1980)

AP Photo

Team: Philadelphia Phillies

Season statistics: 24-9/304/2.34

WAR: 10.2

Bottom line: At 35, Carlton was as stingy on the mound as he was with his words — which is to say, very. His postseason wasn’t too shabby either.

11. Sandy Koufax (1966)

Bill Ingraham / AP Photo

Team: Los Angeles Dodgers

Season statistics: 27-9/323.0/1.73

WAR: 10.7

Bottom line: In the last hurrah before his left arm went out, the 30-year-old Koufax established career highs in games started (41), complete games (27), wins and earned run average. The GOAT of the expansion era flamed out too early, but he left nothing on the field.

10. Zack Greinke (2009)

Charlie Riedel / AP Photo

Team: Kansas City Royals

Season statistics: 16-8/229.1/2.16

WAR: 10.4

Bottom line: Never mind the Cy Young Award. Greinke should also have been the American League Most Valuable Player. Without him, the Royals (65-97) would have finished in the American Association. But nooooo, the voters believed 16 other players were more valuable to their teams.

9. Tom Seaver (1973)

AP Photo

Team: New York Mets

Season statistics: 19-10/290.0/2.08

WAR: 10.6

Bottom line: Seaver had competition from Mike Marshall (31 saves, 2.66) and Ron Bryant (24-12, 3.53), but the vote should not have been close. Tom was “terrific” again. The others were merely very good.

8. Sandy Koufax (1963)

Robert Houston / AP Photo

Team: Los Angeles Dodgers

Season statistics: 25-5/311.0/1.88

WAR: 10.3

Bottom line: Koufax won three Cy Young Awards in a span of four seasons (1963-66), and he would have deserved a fourth if each league had one of its own. He also is the only pitcher to appear twice among the top 11 on this list. Isn’t it time for Major League Baseball to rename it the Sandy Koufax Award in tribute to the GOAT of the expansion era?

7. Randy Johnson (2002)

Gene J. Puskar / AP Photo

Team: Arizona Diamondbacks

Season statistics: 24-5/260.0/2.32

WAR: 10.7

Bottom line: At the ripe young age of 38, Johnson was never more dominant than in this season, the second of his consecutive CYA seasons. Then, the Big Unit got lit up in Game 1 of the NLDS, which set the stage for a three-game sweep.

6. Gaylord Perry (1972)

AP Photo

Team: Cleveland Indians

Season statistics: 24-16/342.2/1.92

WAR: 10.8

Bottom line: The runner-up to Bob Gibson two years earlier, Perry had a career year to edge out Wilbur Wood (24-17, 2.51) in his American League debut. This just goes to show that a spitball can be highly effective in either league when thrown properly and (somewhat) discreetly.

5. Bob Gibson (1968)

AP Photo

Team: St. Louis Cardinals

Season statistics: 22-9/304.2/1.12

WAR: 11.2

Bottom line: Why isn’t Gibson and his legendary season at the top of the list? Because 1968 was the Year of the Pitcher — the average National League pitcher had a 2.99 ERA — his numbers aren’t quite as outrageous as they appear to be. Still, he had a sub-1.00 ERA as late as Sept. 5. Dude, a 1-0 count was a rally against him.

4. Pedro Martinez (2000)

Charles Rex Arbogast / AP Photo

Team: Boston Red Sox

Season statistics: 18-6/217.0/1.74

WAR: 11.7

Bottom line: On the heels of a phenomenal 1999 Cy Young Award season, Martinez did the unimaginable — he got even better. His 5.3 hits allowed per nine innings have remained the standard for 30 years.

3. Roger Clemens (1997)

Ted Mathias / AP Photo

Team: Toronto Blue Jays

Season statistics: 21-7/264.0/2.05

WAR: 11.9

Bottom line: Because Clemens spent all except five of his 24 seasons with Boston and New York teams, it’s easy to forget his two-year stint north of the border. The first was his most dominant virtually across the board. He led the league in seven major categories.

2. Steve Carlton (1972)

Bill Ingraham / AP Photo

Team: Philadelphia Phillies

Season statistics: 27-10/346.1/1.97

WAR: 12.1

Bottom line: The otherwise lame Phillies won 59 games in this lockout-shortened season. Carlton accounted for nearly half of them. If an average pitcher had made his 41 starts, they would have had a 47-109 record. Heck, that borders on ’62 New York Mets territory. That The Sphinx received one first-place vote in the Most Valuable Player election remains one of the greatest travesties in modern baseball history.

1. Dwight Gooden (1985)

AP Photo

Team: New York Mets

Season statistics: 24-4/276.2/1.53

WAR: 12.2

Bottom line: I could ramble on about this historic performance. Because I’m on a word count, I’ll just say this: Since the start of the 20th Century, only Walter Johnson (twice) and Cy Young himself had higher WAR totals in one season. At 20, Doc had his future in front of him, but he was never a 20-game winner again. Damn those demons, anyway.