How They Got There: The 1990-1999 AL Cy Young Winners

As baseball players continued to get bigger and stronger throughout the 1990s — by various legal and illegal means — the game was changing rapidly. Starting pitchers began throwing with ever increasing velocity. Meanwhile, a decrease in a typical starting pitcher’s innings per game, a heavier reliance on the bullpen, and a greater likelihood of injury — all trends that continue in today’s game — were all becoming part of this new era of baseball.

While the game became more favorable towards hitters, many of the best pitching performances during this era are legendary. Here’s a look back at how the AL Cy Young winners of the 1990s were acquired.

1990 AL Cy Young
Rank Name Team Age How Acquired W L IP ERA FIP WAR
CY Bob Welch OAK 33 Trade (LAD) Dec’87 27 6 238.0 2.95 4.19 1.8
2nd Roger Clemens BOS 27 Drafted 1st Rd (19) ’83 21 6 228.1 1.93 2.18 8.2
3rd Dave Stewart OAK 33 Free Agent (PHI) May’86 22 11 267.0 2.56 3.33 4.9

After a successful 10 year stint with the Los Angeles Dodgers, the team that drafted him in the first round (20th pick overall) of the 1977 amateur draft, Bob Welch was traded to the Oakland Athletics following the 1986 season in a three-team, eight-player deal with the Los Angeles Dodgers and New York Mets. The A’s, believing they were a team on the rise and close to playoff contention, fulfilled an offseason goal of adding a veteran starting pitcher to pair with Dave Stewart, who had just had his first of what would end up being four consecutive 20-win seasons.

In his debut season with the A’s, Welch won a career-high 17 games, helping his team capture a division title and a World Series appearance. This was followed by another 17-win season that ended with a World Series championship in 1989. While he would spend another five seasons in the majors, 1990 would be one for the ages.

With assistance from one of the best bullpens in the game and, arguably, the best offense, the 33-year-old Welch won an astounding 27 games in 35 starts. But he also had a sub-3.00 ERA and allowed two earned runs or fewer in 60% of his starts, making it easy for his teammates to finish the game with a lead.

Sure, it was clear to most observers that Roger Clemens was the best pitcher in baseball. But that was no longer a huge story. He had already won two Cy Young awards and wasn’t slowing down a bit. As can happen, even today, voters will focus on the shiny new thing. In this case, that would be the “27 wins,” which hadn’t been achieved since Steve Carlton did it in 1972 and hasn’t been accomplished since.

1991 AL Cy Young
Rank Name Team Age How Acquired W L IP ERA FIP WAR
CY Roger Clemens BOS 28 Drafted 1st Rd (19) ’83 18 10 271.1 2.62 2.57 8.5
2nd Scott Erickson MIN 23 Drafted 4th Rd ’89 20 8 204.0 3.18 3.76 3.2
3rd Jim Abbott CAL 23 Drafted 1st Rd (8) ’88 18 11 243.0 2.89 3.27 5.5

Seventeen teams passed on an All-American pitcher out of the University of Texas at Austin named Roger Clemens, including the Seattle Mariners twice (picks seven and 17). With the first overall selection, the Minnesota Twins drafted right-handed pitcher Tim Belcher, who they were unable to sign.

Within a year, those teams were regretting the decision to draft any other player but Clemens. The 21-year-old was already turning heads as a rookie and was only two years away from winning his first Cy Young award.

By 1991, the “Rocket” already had 116 career wins and 1424 strikeouts — he’d finish his career with more than triple each of those totals — and was coming off of a year in which he finished second in Cy Young voting despite 21 wins and a sub-2.00 ERA. While Belcher, who overshadowed him in the 1983 draft, turned in one of the best seasons of his 14-year career, Clemens would once again steal the show.

1992 AL Cy Young
Rank Name Team Age How Acquired W Sv IP ERA FIP WAR
CY Dennis Eckersley OAK 37 Trade (CHC) Apr’87 7 51 80.0 1.91 1.72 3.1
Rank Name Team Age How Acquired W L IP ERA FIP WAR
2nd Jack McDowell CHW 26 Drafted 1st Rd (5) ’87 20 10 260.2 3.18 3.41 4.8
3rd Roger Clemens BOS 29 Drafted 1st Rd (19) ’83 18 11 246.2 2.41 2.54 7.6

On an A’s team with superstars Rickey HendersonJose CansecoMark McGwire, and Dave Stewart, it was 37-year-old closer Dennis Eckersley who won the AL MVP (and Cy Young award) in 1992 after becoming just the second pitcher ever to save at least 50 games in a single season.

Eckersley was the premier closer in baseball by 1992, but still relatively new to the role. Following the 1986 season, the 32-year-old appeared to be on the decline after a long, 12-season career that included 359 starts and 151 wins. He also had an alcohol problem, which he acknowledged after the season when he checked into rehab. While he was done as a starting pitcher, chapter two of his big league career was about to begin.

Days before the start of the 1987 season, A’s general manager Sandy Alderson acquired Eckersley from the Chicago Cubs for minor leaguers Brian Guinn, Mark Leonette, and Dave Wilder, none of whom would reached the majors. His first appearance with the team came in relief when he pitched 2 2/3 scoreless innings to hand off a 4-2 lead to closer Jay Howell, who blew the save in the ninth. Manager Tony La Russa continued to take advantage of Eckersley’s ability to pitch multiple innings — he pitched at least four innings in 10 appearances, including two starts — but it was clear by season’s end that his job would be to close out the last inning or two of each win. He was one of the best in the game at that job for the next decade.

This write-up was originally published as part of How They Got There: The 1990-1999 AL MVPs.

1993 AL Cy Young
Rank Name Team Age How Acquired W L IP ERA FIP WAR
CY Jack McDowell CHW 27 Drafted 1st Rd (5) ’87 22 10 256.2 3.37 3.61 5.2
2nd Randy Johnson SEA 29 Trade (MON) May ’89 19 8 255.1 3.24 3.05 7.0
3rd Kevin Appier KCR 25 Drafted 1st Rd (9) ’87 18 8 238.2 2.56 2.90 6.8

With the fifth pick in the 1987 draft, the Chicago White Sox struck gold when they landed right-hander Jack McDowell out of Stanford. The man who would eventually be known as “Black Jack” was one of several players taken in the first round of that draft who panned out, including Hall of Famers Ken Griffey Jr. and Craig Biggio. He was the only one, however, who would make his major league debut later that season.

By 1993, McDowell was one of the best pitchers in baseball, with two All-Star selections and a 20-win season under his belt. His team, however, had not been to the playoffs in 10 years so his performance was all the more noteworthy as it coincided with the White Sox’s only division title and postseason appearance of the 90s.

1994 AL Cy Young
Rank Name Team Age How Acquired W L IP ERA FIP WAR
CY David Cone KCR 31 Free Agent (TOR) Dec’92 16 5 171.2 2.94 3.80 3.8
2nd Jimmy Key NYY 33 Free Agent (TOR) Dec’92 17 4 168.0 3.27 3.73 4.0
3rd Randy Johnson SEA 30 Trade (MON) May ’89 13 6 172.0 3.19 3.18 5.2

Eleven relief appearances into his first stint with the Kansas City Royals, who had selected him in the third round years earlier, David Cone was traded to the New York Mets in March 1987. By the time he returned to his hometown team six seasons later after signing a three-year, $18 million contract, Cone was one of the premier pitchers in the game, a two-time All-Star and World Series champion. He would soon add “Cy Young Award winner” to his resume, although his second stint with the Royals was also a short one.

Prior to Opening Day 1995, the 32-year-old was traded to the Blue Jays. Less than four months later, he was traded to the New York Yankees. Cone had an eventful stint in the Bronx, where he’d pitch a perfect game and collect four more World Series rings over the next five-and-a-half seasons, making it much more difficult to remember him pitching three consecutive shutouts and winning his lone Cy Young award while with the Royals during the strike-shortened 1994 season.

1995 AL Cy Young
Rank Name Team Age How Acquired W L IP ERA FIP WAR
CY Randy Johnson SEA 31 Trade (MON) May ’89 18 2 214.1 2.48 2.08 9.5
Rank Name Team Age How Acquired W Sv IP ERA FIP WAR
2nd Jose Mesa CLE 29 Trade (BAL) Jul’92 3 46 64.0 1.13 2.70 2.1
Rank Name Team Age How Acquired W L IP ERA FIP WAR
3rd Tim Wakefield BOS 28 Free Agent (PIT) Apr’95 16 8 195.1 2.95 4.53 2.6

When the Montreal Expos traded 25-year-old Randy Johnson in a deal to land veteran Mark Langston from the Seattle Mariners in May 1989, the 6-foot-10 lefty didn’t seem like a guy who was close to figuring out how to throw strikes consistently.

At the time, the Expos were a fourth place team, but only three games out in the division. They hadn’t finished higher than third place since 1982, although they had four winning seasons, an 81-win season, and a pair of 78-win seasons during that span. In other words, they were an average team that was desperate to take a step forward. They were not in a place where they could be patient with a young pitcher who had walked 26 batters in 29.2 innings, including six over four innings in his last start.

Johnson was an All-Star for the Mariners in 1990, despite walking close to five batter per nine innings. He was still an effective starter over the following two seasons, despite walking more than six batters per nine innings. But in 1993, Johnson finally “figured it out.” It was the first of 16 consecutive seasons in which he posted a BB/9 rate under 4.0, including 1995 when he won the first of his five Cy Young awards would after leading the league in ERA, strikeouts, and strikeout-to-walk ratio.

1996 AL Cy Young
Rank Name Team Age How Acquired W L IP ERA FIP WAR
CY Pat Hentgen TOR 27 Drafted 5th Rd ’86 20 10 265.2 3.22 3.94 6.0
2nd Andy Pettitte NYY 24 Drafted 22nd Rd ’90 21 8 221.0 3.87 4.08 4.6
Rank Name Team Age How Acquired W Sv IP ERA FIP WAR
3rd Mariano Rivera NYY 26 Amateur FA (PAN) Feb’90 8 5 107.2 2.09 1.88 4.3

In an otherwise unsuccessful 1986 draft, the Toronto Blue Jays made a splash when they chose high school pitcher Pat Hentgen with the 133rd overall pick. After breaking in primarily as a reliever for the Jays in 1992, he was an All-Star the following season, winning 19 regular season games and another in the World Series for the eventual champs. Two years later, Hentgen posted a 5.11 ERA with 14 losses for the last place Jays. He would head into the 1996 season with questions about his ability to bounce back after leading the league in earned runs and hits allowed.

The 27-year-old did more than just bounce back. He was never better, posting a career-low 3.22 ERA while leading the league in innings (265.2), complete games (10), and shutouts (3). And while homers in the American League increased by nearly 600 from the previous season, Hentgen led the league with an 0.7 HR/9 rate. Perhaps Andy Pettitte, a 21-game winner on a first place Yankees team, should’ve given him the edge in a close race, but Hentgen’s previous success and new-found ability as a workhorse — he completed at least eight innings in more than half of his starts — likely pushed him over the top.

1997 AL Cy Young
Rank Name Team Age How Acquired W L IP ERA FIP WAR
CY Roger Clemens TOR 34 Free Agent (BOS) Dec’96 21 7 264.0 2.05 2.25 10.7
2nd Randy Johnson SEA 33 Trade (MON) May ’89 20 4 213.0 2.28 2.82 7.0
3rd Brad Radke MIN 24 Drafted 8th Rd ’91 20 10 239.2 3.87 3.81 4.9


1998 AL Cy Young
Rank Name Team Age How Acquired W L IP ERA FIP WAR
CY Roger Clemens TOR 35 Free Agent (BOS) Dec’96 20 6 234.2 2.65 2.65 8.2
2nd Pedro Martinez BOS 26 Trade (MON) Nov’97 19 7 233.2 2.89 3.40 5.7
3rd David Wells NYY 35 Free Agent (BAL) Dec’96 18 4 214.1 3.49 3.80 4.4

Following the 1996 season, 34-year-old free agent Roger Clemens would pass on a four-year, $32 million guarantee from the New York Yankees in favor of a three-year, $24.75 million contract with the Blue Jays. The Yankees would “settle” for free agent and former Blue Jays pitcher David Wells, who would win 34 games over the next two seasons and help lead the team to a World Championship in 1998.

One of the most dominant pitchers in baseball from 1986-1992, Clemens had no All-Star appearances or Cy Young votes over the previous four seasons. Despite the decline in performance, his value was high — the contract with Toronto made him the highest-paid pitcher in baseball history — because he was the “Rocket” and still very good by most standards. Clemens would return to his old form, however, giving the Blue Jays two of his best seasons ever, leading the league in wins, ERA, and strikeouts.

The Yankees would finally get their man when they acquired Clemens prior to the 1999 season in a deal that included Wells, who would win 37 games for Toronto in 1999 and 2000. Clemens would get his two World Series rings in 1999 and 2000, and after crossing paths for years, he’d join forces with Wells when both pitched for the Yankees during their ages 39-40 seasons in 2002 and 2003.

1999 AL Cy Young
Rank Name Team Age How Acquired W L IP ERA FIP WAR
CY Pedro Martinez BOS 27 Trade (MON) Nov’97 23 4 213.1 2.07 1.39 11.6
2nd Mike Mussina BAL 30 Drafted 1st Rd (20) ’90 18 7 203.1 3.50 3.25 6.0
Rank Name Team Age How Acquired W Sv IP ERA FIP WAR
3rd Mariano Rivera NYY 29 Amateur FA (PAN) Feb’90 4 45 69.0 1.83 2.92 2.1

At 25 years of age, Pedro Martinez had established himself as one of the best pitchers in baseball with one of the greatest single-season pitching performances of all-time in 1997. Heading into his final season before free agency, it was clear that he wouldn’t be sticking around with the small-market Montreal Expos, who had already shed their roster of most high-priced talent and were ready to build around a young and inexpensive superstar named Vladimir Guerrero.

The Expos traded Martinez to the Boston Red Sox on November 18, four years after acquiring him from the Los Angeles Dodgers in a lopsided deal for Delino DeShields. The general manager acquiring the future Hall of Famer in both cases was Dan Duquette, who had left Montreal for Boston prior to the 1994 season. In return for one year of their ace, the Expos received pitching prospects Carl Pavano, who Baseball America ranked as their second best prospect behind Nomar Garciaparra, and Tony Armas Jr.

After falling short in the AL Cy Young race after his debut season in Boston — Clemens won the award unanimously — the 27-year-old Martinez would prove that he was head and shoulders above the competition in 1999. In a season in which American League starting pitchers had a 5.03 ERA, Martinez was nearly a run better than teammate Bret Saberhagen, who was second in the league with a 2.95 ERA, and had 106 more strikeouts than Chuck Finley, who was second in the league.

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2 years ago

My main takeaway from this argument is that it’s ridiculous to use Cy Youngs for/against a player’s Hall of Fame worthiness. At least half the winners here shouldn’t have won

Six Ten
2 years ago
Reply to  Dmjn53

If Cy Young awards won is a primary factor that’s absolutely true. But when you drill down into this list, it doesn’t feel nearly so important.

5/10 wins in this article were deserved according to fWAR. So it’s “at most half” not at least half who shouldn’t have won with any certainty. So let’s talk about the half that shouldn’t have won.

Welch and Eckersley were clearly bad choices, but Eck absolutely deserves to be in the Hall anyway, and 3.1 WAR for a reliever is impressive as hell. And Welch was never anywhere close, so it’s not a useful part of any argument; there’s just no argument to be had there.

Pat Hentgen shouldn’t have won; he looks great in this article because the top two by fWAR (Clemens and Appier) didn’t make the top three vote getters. McDowell also shouldn’t have won, clearly. Those two both had careers that at one point seemed headed for marginal Hall-worthiness, but they fell off enough that it wasn’t ever a close call. If it was close, we’d have a point to argue.

That really only leaves one where an iffy Cy Young might have been a difference maker for an iffy Hall of Fame resume: David Cone. But using fWAR alone makes the injustice of it seem bigger than it was. Cone actually led all AL pitchers in bWAR (6.9 vs Clemens’s 6.0). So it’s more legit than it first looks here.

Career stats tell us a lot more than any award about how good someone was. But, to resort to a cliché, we don’t watch for the stats, we watch for the memorable things that happen. If we’re looking at a borderline HoF guy, I think it’s perfectly fine to mention “And there was that year when people who watch a lot of baseball decided to say he was the best pitcher in the game” as part of the argument. Some people watched and remembered and were impressed. And that matters.

2 years ago
Reply to  Dmjn53

The only questionable one on here was 1990. The rest are fine.