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

Whether you’re assembling a fantasy baseball team or a real-life one, my number one rule is to never trust pitchers. Don’t trust that a pitcher will stay healthy. And even if they can avoid an extended stint on the Injured List, don’t trust a pitcher to put up numbers that resemble any previous season.

But even in the wildly unpredictable game of baseball, there is a very small group of starting pitchers who stand above the rest due to a rare combination of command, stuff, consistency, and durability. The winners of the Cy Young Award often come from this group of aces. Several have won the award multiple times. Twenty-one pitchers have accounted for more than half of the 118 Cy Young awards handed out since the honor was created in 1956 (Don Newcombe was the first recipient).

Back in 1981, a 19-year-old rookie named Fernando Valenzuela won the hearts of Cy Young voters after “Fernandomania” ran wild through the baseball world. But he’s the rare exception, an overnight sensation who won the award. The Cy Young typically goes to well-established stars with track records of success. Where they differ is the beginning of their paths and how it led them to their respective team.

Here’s a look back at how the NL Cy Young winners of the 1990s were acquired.

1990 NL Cy Young
Rank Name Team Age How Acquired W L IP ERA FIP WAR
CY Doug Drabek PIT 27 Trade (NYY) Nov’86 22 6 231.1 2.76 3.28 4.2
2nd Ramon Martinez LAD 22 Amateur FA (DOM) Sep’84 20 6 234.1 2.92 3.03 4.9
3rd Frank Viola NYM 30 Trade (MIN) Jul’89 20 12 249.2 2.67 2.88 5.8

When you think of the players on the great Pittsburgh Pirates teams that won three consecutive division titles from 1990-92, Barry Bonds is the first name that comes to mind for most. But Bonds, though he considered the greatest baseball player on the planet at the time, couldn’t do it all by himself. The Pirates pitching staff was one of the best in baseball over that three-year span, too, and the leader of that group was Doug Drabek, a twice-traded former 11th round draft pick of the Chicago White Sox.

After falling shy of the playoffs in 1986, the New York Yankees were looking to improve their starting rotation the following offseason. Rick Rhoden, a 15-game winner and an All-Star for the Pirates, was their target. To acquire the 33-year-old veteran and a pair of relievers (Pat Clements and Cecilio Guante), the Yankees sent pitchers Logan Easley, Brian Fisher, and Drabek, who Baseball America had ranked as their fourth best pitching prospect during the previous offseason, to the Pirates.

While Rhoden was solid in his two seasons with the Yankees, winning 28 games and posting a 4.09 ERA, Drabek quickly progressed from holding his own to reliable workhorse to Cy Young winner.

1991 NL Cy Young
Rank Name Team Age How Acquired W L IP ERA FIP WAR
CY Tom Glavine ATL 25 Drafted 2nd Rd (47) ’84 20 11 246.2 2.55 3.06 5.4
Rank Name Team Age How Acquired W Sv IP ERA FIP WAR
2nd Lee Smith STL 33 Trade (BOS) May’90 6 47 73.0 2.34 2.44 2.0
Rank Name Team Age How Acquired W L IP ERA FIP WAR
3rd John Smiley PIT 26 Drafted 12th Rd ’83 20 8 207.2 3.08 3.36 3.4

Selected by the Braves in the second round of the MLB draft, 16 picks after future teammate Greg Maddux, and by the Los Angeles Kings in the fourth round of the NHL draft, Tom Glavine had to make a choice following his senior year at Billerica High School in Massachusetts. He chose baseball.

At the time Glavine joined the Braves’ organization, things were headed in the wrong direction. The team was about to endure one of their worst runs in franchise history. From 1985-1990, they averaged 96 losses and had four last-place finishes. Since moving to Atlanta 25 seasons earlier, they had two post-season playoff appearances and zero wins.

But in 1991, they would begin a string of 15 straight winning seasons, which included 14 division titles and a World Series championship. And the face of the team’s newfound success was Glavine, one of a trio of young pitchers, along with Steve Avery and John Smoltz, who the team had been pointing to as a sign of hope during its bleakest moments.

1992 NL Cy Young
Rank Name Team Age How Acquired W L IP ERA FIP WAR
CY Greg Maddux CHC 26 Drafted 2nd Rd (31) ’84 20 11 268.0 2.18 2.58 7.0
2nd Tom Glavine ATL 26 Drafted 2nd Rd (47) ’84 20 8 225.0 2.76 2.94 4.6
3rd Bob Tewksbury STL 31 Free Agent (CHC) Dec’88 16 5 233.0 2.16 3.14 4.0

If a pitcher you draft in the second round wins 133 games and a Cy Young award in more than eight seasons for your team, you’d normally think that you really can’t ask for much more than that. But when that pitcher — let’s call him Greg Maddux — wins three Cy Young awards and 194 games for another team — we’ll call them the Atlanta Braves — you’d probably feel like you got the short end of the stick.

Still, Maddux alone made the Cubs’ 1984 draft a success even if their first round pick, Morehouse State pitcher Drew Hall, was a bust, and fourth round pick Jamie Moyer only spent three of his 25 major league seasons with the team. Both Hall and Moyer, along with Rafael Palmeiro, were traded to the Texas Rangers in December 1988 for six players, including Mitch Williams.

1993 NL Cy Young
Rank Name Team Age How Acquired W L IP ERA FIP WAR
CY Greg Maddux ATL 27 Free Agent (CHC) Dec’92 20 10 267.0 2.36 2.85 7.5
2nd Bill Swift SFG 31 Trade (SEA) Dec’91 21 8 232.2 2.82 3.43 4.5
3rd Tom Glavine ATL 27 Drafted 2nd Rd (47) ’84 22 6 239.1 3.20 4.01 3.3


1994 NL Cy Young
Rank Name Team Age How Acquired W L IP ERA FIP WAR
CY Greg Maddux ATL 28 Free Agent (CHC) Dec’92 16 6 202.0 1.56 2.39 7.4
2nd Ken Hill MON 28 Trade (STL) Nov’91 16 5 154.2 3.32 4.01 2.3
3rd Bret Saberhagen NYM 30 Trade (KCR) Dec’91 14 4 177.1 2.74 2.76 5.4


1995 NL Cy Young
Rank Name Team Age How Acquired W L IP ERA FIP WAR
CY Greg Maddux ATL 29 Free Agent (CHC) Dec’92 19 2 209.2 1.63 2.26 7.9
2nd Pete Schourek CIN 26 Waivers (NYM) Apr’94 18 7 190.1 3.22 3.42 4.2
3rd Tom Glavine ATL 29 Drafted 2nd Rd (47) ’84 16 7 198.2 3.08 3.49 4.3

It’s not like the Cubs didn’t try to hold on to Maddux, who had been trending upwards for years but only began to emerge as an ace in his final season before becoming a free agent. After turning down their five-year, $27.5 million offer during the 1992 season, Maddux did slightly better in free agency when he agreed to a five-year, $28 million contract with the Braves.

In choosing a team that had won the NL Championship in back-to-back seasons and already had one of the best rotations in baseball over the Cubs and Yankees, both fourth place teams in 1992 — reportedly the Braves’ top competition for Maddux — he made clear that winning a championship was his top priority.

1996 NL Cy Young
Rank Name Team Age How Acquired W L IP ERA FIP WAR
CY John Smoltz ATL 29 Trade (DET) Aug’87 24 8 253.2 2.94 2.64 8.4
2nd Kevin Brown FLA 31 Free Agent (BAL) Dec’95 17 11 233.0 1.89 2.88 6.7
3rd Andy Benes STL 28 Free Agent (SEA) Dec’95 18 10 230.1 3.83 4.44 2.4

As MLB Network’s Casey Stern likes to say, “Prospects are cool. Parades are cooler.” He’s not wrong. More often than not, making a win-now gamble to try to push a team over the top won’t come back to hurt in a big way. Prospects are often over-hyped and years away from approaching their potential. By the time they reach the majors, most fans will have forgotten who they were even acquired for. That is, unless that player turns out to be one of the best in the game. Then everybody remembers. And they bring it up. All the time.

On August 12, 1987 the Detroit Tigers were only 1 1/2 games behind the first place Toronto Blue Jays after trailing by as much as 11 games in early May. They determined that starting pitcher Doyle Alexander would further assist them down the stretch and that trading away their best pitching prospect, John Smoltz, was worth the risk. Whether or not it was is arguable.

The 36-year-old Alexander was at his best, posting a 9-0 record and 1.53 ERA in 11 starts as the Tigers won the AL East before losing to the Minnesota Twins in the ALCS. He was an All-Star for the first and only time in 1988. Smoltz made his first of eight All-Star teams in 1989, which was Alexander’s last season.

1997 NL Cy Young
Rank Name Team Age How Acquired W L IP ERA FIP WAR
CY Pedro Martinez MON 25 Trade (LAD) Nov’93 17 8 241.1 1.90 2.39 8.5
2nd Greg Maddux ATL 31 Free Agent (CHC) Dec’92 19 4 232.2 2.20 2.43 8.0
3rd Denny Neagle ATL 28 Trade (PIT) Aug’96 20 5 233.1 2.97 3.34 5.2

In November 1993, the Montreal Expos acquired the undervalued Pedro Martinez from the Los Angeles Dodgers for Delino DeShields, who was overvalued after hitting over .290 with more than 40 stolen bases in back-to-back seasons. At the time, DeShields for Martinez, an undersized pitcher with durability questions, did not appear to be a lopsided trade. The Dodgers were looking for a leadoff man and a second baseman. The Expos were looking for a starting pitcher to replace veteran free agent Dennis Martinez. It seemed like a good value-for-value match that filled needs for each side. It was not.

While DeShields disappointed in Los Angeles, the Expos got three good seasons out of Martinez before he broke out in year four to win his first of three Cy Young awards. With a rebuild on the horizon, the Expos had a golden opportunity to turn Martinez’s final season before free agency into a prospect haul. He was traded to the Red Sox for prospects Carl Pavano and Tony Armas Jr. The golden opportunity was wasted.

1998 NL Cy Young
Rank Name Team Age How Acquired W L IP ERA FIP WAR
CY Tom Glavine ATL 32 Drafted 2nd Rd (47) ’84 20 6 229.1 2.47 3.50 4.8
Rank Name Team Age How Acquired W Sv IP ERA FIP WAR
2nd Trevor Hoffman SDP 30 Trade (FLA) Jun’93 4 53 73.0 1.48 2.04 3.1
Rank Name Team Age How Acquired W L IP ERA FIP WAR
3rd Kevin Brown SDP 33 Trade (FLA) Dec’97 18 7 257.0 2.38 2.23 9.6

Ten seasons and 150 wins into his career in the big leagues, Glavine was still going strong. The Braves, not even at the halfway point of their aforementioned 15-year run, were continuing to add young talent from their farm system and make key trade and free agent acquisitions.

Aside from Smoltz, the roster had been completely made over since Glavine had won his first Cy Young award seven years earlier. But it was the same ol’ Glavine: 20 wins in both seasons and nearly identical stat lines. He even had 17 hits in each season.

1999 NL Cy Young
Rank Name Team Age How Acquired W Sv IP ERA FIP WAR
CY Randy Johnson ARI 35 Free Agent (HOU) Dec’98 17 9 271.2 2.48 2.76 9.5
2nd Mike Hampton HOU 26 Trade (SEA) Dec’93 22 4 239.0 2.90 3.64 4.9
3rd Kevin Millwood ATL 24 Drafted 11th Rd ’93 18 7 228.0 2.68 3.53 5.5

It wasn’t a huge surprise when Randy Johnson signed with the Arizona Diamondbacks following the 1998 season. After all, he was a resident of nearby Paradise Valley, a suburb of Phoenix. And at four years and $52.4 million, he wasn’t taking a hometown discount. But at the age of 35, with no World Series rings and only three post-season appearances during a career that spanned over a decade, the Big Unit was taking a big chance that a 97-loss team heading into its second year of existence would make a quick rise into playoff contention.

As it turned out, Johnson’s window for winning a championship was much wider than anyone could’ve expected. He would go on to pitch another 11 years, although he would get his World Series ring (and a World Series MVP award) within three. He would also win four consecutive Cy Young awards in his ages 35-38 seasons, one of the most amazing feats in baseball history.

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4 years ago

The 90s were great.

4 years ago

Yeah, mostly strong economy, balanced national budget for a while, not much terrorism aside from a major incident in Oklahoma City, the only major military action was a sound victory in defense of Kuwait, the Internet went public, computer technology in general improved exponentially, animated entertainment was at its peak, and the Cubs were still the lovable losers for the most part.

Pirates Hurdles
4 years ago
Reply to  Lanidrac

Forgot that Rock’nRoll had its last great stand as well.

4 years ago

Robert Downey Jr. disagrees