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Pinstripe Alley Top 100 Yankees: #95 Jimmy Key

The southpaw will go down as one of the best starters in Jays history, but his move to the Yankees helped usher in the turn-of-the-millennium dynasty era.

New York Yankees’ starting pitcher Jimmy Key during game aga Photo by Linda Cataffo/NY Daily News Archive via Getty Images

Full Name: James Edward “Jimmy” Key
Position: Starting pitcher
Born: April 22, 1961 (Huntsville, AL)
Yankee Years: 1993-96
Primary number: 22
Yankee statistics: 48-23, 3.68 ERA, 3.87 FIP, 94 GS, 604.1 IP, 400 K, 80 ERA-, 84 FIP-, 13.5 rWAR, 12.4 fWAR


The 1980s were a challenging period for the Yankees, as they were never able to capitalize on a potent lineup that consisted of the likes of Don Mattingly, Dave Winfield and Rickey Henderson thanks to a perennial dearth of quality pitching. This only worsened as the decade flipped over to the ‘90s, as the team posted four consecutive sub-.500 campaigns from 1989-92.

A change was needed, and heading into the 1993 season, the Yankees brought in the 31-year-old Jimmy Key to head their rotation. The signing of the admittedly unheralded southpaw away from the division rival and reigning World Series champion Blue Jays served as one of the primary signals of New York’s shift toward championship-caliber pitching to complement their reliably dangerous bats.

Growing up in Alabama

James Edward “Jimmy” Key was born April 22, 1961, in Huntsville, Alabama to Carol — a 30-year employee for NASA — and Ray Key, a US Army Engineer for 35 years. From the very beginnings of his interest in baseball, Key’s father was a stern mentor. He prohibited his son from throwing hard or simply playing catch, stating that if Key “wasn’t going to throw to a catcher, then [he] was wasting [his] time.” Instead, Ray preached the importance of precise control, something which his son would come to epitomize during his playing career.

The strict coaching paid off, Key becoming the dominant leader of the S.R. Butler High School pitching staff. His senior year, Key went 10-0 with nine shutouts and a 0.30 ERA while also batting .410 with 11 home runs and 35 RBI as the team’s DH. It was enough to attract the attention of the White Sox, who attempted to draft Key in the 10th round of the 1979 amateur draft. However, Key had another enticing offer from National College Baseball Hall of Fame coach Bill Wilhelm of Clemson University:

“Gene Compton, a former Clemson player who was living in Huntsville, kept telling me about this left-hander that I had to see. He was being heavily recruited by all the schools, so I made the trip to Birmingham to watch him pitch in the state quarterfinal game in front of 4,000 people. He struck out 19 batters in 11 innings and won 1-0. I was so impressed that I went up to him after the game and offered him a full scholarship. Without any hesitation and ever seeing Clemson, he said, ‘I’ll take it.’ He was certainly one of the easiest to recruit.”

At Clemson, Key continued to refine his craft, leading the staff as a freshman in starts (15) and innings pitched (111.1) en route to being named the Game 1 starter of the 1980 College World Series. After experiencing slight regression on the mound as a sophomore, Key truly put it all together his junior year, becoming the first Clemson player to be receive All-ACC first-team honors at two positions: pitcher and DH.

Key finished the year with an ACC-best nine wins (including seven complete games) and a 2.79 ERA. He also led the team by batting .359, slugging a then-school record 21 doubles along with four home runs, 49 RBI, and eight stolen bases.

Quietly making a name in Toronto

The Blue Jays of the ‘80s and ‘90s boasted some of the most fearsome rotations across the sport. When you start for a team that also boasted the likes of Dave Stieb, David Cone, Jack Morris, and later Roger Clemens, it’s easy to get overshadowed by their oversized performances on the field and personalities off it. For some players, this might have been an intimidating scenario, but for the stoic and introspective Key, it was likely just how he wanted it.

Following his standout performances at Clemson, Toronto selected Key in the third round of the 1982 amateur draft, one round after they selected David Wells. Key spent just two years in the minor leagues, pitching to a 3.38 ERA in 44 appearances across all four levels before making the major-league squad out of spring training in 1984. He made his MLB debut as a reliever on April 6, 1984, tossing 3.1 innings of scoreless relief to close out an 11-5 victory over the Angels, and finished the year with a 4.65 ERA in 63 appearances.

Nonetheless, his rookie campaign impressed manager Bobby Cox enough for a promotion to the starting rotation. Key responded by earning the first of five All-Star nods, pitching to a 3.00 ERA (141 ERA+) with 85 strikeouts across 32 starts totaling 212.2 innings as Toronto picked up its first division title and a franchise-record 99 wins that still stands to this day. Unfortunately, Key got roughed up in Games 2 and 5 of the ALCS as Toronto blew a 3-1 series lead to the eventual World Series champion Royals.

Perhaps motivated by this first taste of adversity, Key turned in the best season of his career two years later. The southpaw led MLB with a 2.76 ERA (164 ERA+) and 1.057 WHIP, going 17-8 in 36 starts totaling 261 innings en route to a career-best 5.6 fWAR and second-place AL Cy Young finish behind Roger Clemens. Unfortunately, a seven-game losing streak by the Blue Jays to end the season saw them pipped to the AL East title — and a berth in the postseason — by the Tigers.

He would have to wait six years between his first and second All-Star selections, the second coming in a 1991 campaign in which Key went 16-12 in 33 starts with a 3.05 ERA (139 ERA+) in 209.1 innings to rack up his second five-plus win season by FanGraphs’ calculations. It helped Toronto capture their third AL East title, though they would fall in five games to the eventual-champion Twins with Key spoiling the early lead he had been given in Game 3.

After coming up short in multiple postseasons, the Blue Jays finally got their revenge by securing their first AL pennant in six games over the A’s, helped by the trade deadline acquisition of Cone from the Mets to give them a playoff rotation of Cone, the aforementioned Morris, and underrated contributor Juan Guzmán. Key may have played a bit part in the ALCS, making just one appearance out of the bullpen, but his performances in the Fall Classic were indispensable to the Blue Jays exorcising their playoff demons.

Facing the nascent juggernaut Braves in the 1992 World Series, Toronto manager Cito Gaston handed Key his World Series debut, naming him the starter of Game 4 against Game 1 starter Tom Glavine. Key outdueled the NL Cy Young winner from the prior season, tossing 7.2 sparkling innings, holding Atlanta to a run on five hits before being pulled for Duane Ward. As he was in the final year of his contract, the Blue Jays crowd sensed that they may have witnessed Key’s final pitch for the team, and treated him to a rapturous standing ovation as he walked off the mound, tipping his cap to those showing their appreciation.

It would end up as his penultimate act in Blue Jays colors as the Braves fought back from the brink of elimination, taking Game 5 at the SkyDome to send the series back to Fulton County Stadium. With two outs in the bottom of the ninth facing closer Tom Henke — who only two games earlier set down the side in order to put his team on the precipice of a title — the Braves rallied to send the game to extra innings.

Gaston turned to Key with one out in the 10th, and the lefty held the Braves in check long enough to become the pitcher of record when Dave Winfield’s two-run double in the top of the 11th gave the Blue Jays the decisive lead. Though Key would surrender a run in the bottom half, Mike Timlin sealed the title on an Otis Nixon bunt groundout to make Key the winning pitcher and the Blue Jays World Series champions for the first time.

1992 World Series Game 4 Photo by MLB via Getty Images

Into the New York spotlight

Growing tired of the mounting streak of losing seasons, George Steinbrenner targeted the superstar-studded free agent class of 1993 in an attempt to restore the Yankees to championship contention. As it happens, that free agency could scarcely have started worse for the Yankees, with Barry Bonds spurning the Bombers for San Francisco and reigning NL Cy Young winner Greg Maddux accepting $6 million less than the Yankees’ offer to join Atlanta.

After he also whiffed on number two target Cone and on the advice of GM Gene “Stick” Michael, Steinbrenner pivoted to Key.

Michael called Key “the best control pitcher in the game. When you think about an artist painting a picture or a genius on the mound, he is it. Obviously, he’s smarter than the hitters.”

The Yankees initially tendered a four-year, $16 million deal, besting the Blue Jays’ offer as they had a strict policy of not offering more than three years to a pitcher. Represented by his wife Cindy Key — owner of a business administration degree from Clemson and at the time one of only five female agents representing major league players — the Keys countered asking for an additional $1 million in the third year of his contract. After never hearing back from the Blue Jays, Key accepted the Yankees’ offer from the cabin of his cruise ship vacation to Hawaii on December 10, 1992.

There are always questions of how a player will adapt to the bright lights of New York. However, Cindy never had any doubts about her husband’s ability to handle the pressure, calling her husband, in a word, un-crushable.

“Jimmy has never kicked or broken anything in the clubhouse. If it were me, I’d snap every once in a while. I think that’s normal. I’d like to see some emotion sometimes. But I have accepted the fact that that’s his nature. If he did change it, it would probably be a detriment to his career. Because he doesn’t have an overpowering fastball and isn’t intimidating in that way, he compensates with location. In order to have great location, he can’t be overly excited or he’ll lose it. A long time ago, he learned the only way he’d make it to the major leagues is by control. That really made him into the player he is.”

Key echoed these sentiments, minimizing the frenzy of the New York media market, the rabid fanbase and the unstable situation from clubhouse to front office he was stepping into:

“The thing I couldn’t understand is that people couldn’t see me pitching here. If anybody’s perfect for this atmosphere, it’s me. I’m not trying to blow myself up. But my personality is as good as anybody’s for facing distractions. No outside factor has ever bothered me. I guess that means I should fit New York pretty well.”

His statements could not have been more accurate, rocketing himself up the rotation pecking order to become the ace of Buck Showalter’s staff. In his debut Yankee season of 1993, Key went 18-6 in 34 starts totaling 236.2 innings, with a 3.00 ERA (139 ERA+) and AL-best marks in walks per nine (1.6) and strikeout-to-walk ratio (173:43). It gave Key his third and final five-plus win season per FanGraphs, third All-Star selection and an eventual fourth-place finish in Cy Young voting.

More importantly, Key established himself as a leader in the beginning stages of a new era for the Yankees, as alongside captain Don Mattingly, fellow free agent additions Paul O’Neill and Wade Boggs, and the up-and-coming Bernie Williams, New York improved to a second-place finish in the division. They may have had to watch Key’s old teammates in Toronto capture the first back-to-back titles since the Bombers’ own achievement in 1977-78, but there was clearly something exciting brewing in the Bronx.

Key followed that 1993 campaign up with his best season in pinstripes from an awards voting perspective. He earned back-to-back All-Star nods, finishing the strike-shortened 1994 season with an MLB-best 17 wins and 3.27 ERA (140 ERA+) in 25 starts totaling 168 innings, leading the AL in starts and home runs per nine (0.5) to earn his second runner-up Cy Young finish (behind Cone in Kansas City) and even a sixth-place finish in MVP balloting.

With the Yankees having emerged as the AL’s most dangerous squad, they were champing at the bit for a postseason appearance after being denied that opportunity in ‘94. Unfortunately for Key, he saw his 1995 season cut short after just five starts by what was first diagnosed as shoulder tendinitis but later was revealed as a far more serious injury to his left rotator cuff, necessitating surgery. He had to watch from the sidelines as the Yankees and deadline acquisition Cone sneaked in as the inaugural AL Wild Card, only to squander a 2-0 lead by losing three straight to the Mariners.

1996: Launching a dynasty

The Yankees boasted a new manager in Joe Torre and a new-look rotation heading into 1996, but change isn’t always a guarantor of improved results. On the contrary, uncertainty abounded the staff outside of the re-signed Cone. Key was returning from his fourth major arm injury, Andy Pettitte was only embarking on his second season, and newcomers Kenny Rogers and Dwight Gooden arrived with wide error bars for varying reasons. Things only took a turn for the worse when Cone required emergency surgery to remove an aneurysm in his pitching arm that limited him to just 11 starts in the regular season.

However, Key rose to the moment. Learning how to manage pitching and recovery with a reconstructed shoulder, Key missed just four starts in ‘96, finishing 12-11 with a 4.68 ERA (107 ERA+) in 30 starts totaling 169.1 innings while also taking the young Pettitte under his wing, helping the fellow southpaw with his pickoff move. Thankfully for the Bombers, 1996 marked the transition of the team into an offensive powerhouse, ushered in by the arrival of eventual AL Rookie of the Year Derek Jeter and strong campaigns at the plate for Williams, O’Neill, and trade addition Tino Martinez. The regular season ended with the Yankees winning 92 games to claim their first division crown in 15 years.

Facing the Rangers in Game 3 of the ALDS, Key limited the potent Rangers lineup to two runs in five innings on a Juan Gonzalez solo shot in the fourth — his fourth in three games — and an Ivan Rodriguez RBI double in the fifth. However, opposing starter Darren Oliver imposed his will on the Yankees lineup for eight innings following a Williams homer in the first, the Bombers requiring a two-run ninth inning rally via a Williams sac fly and Mariano Duncan RBI single to grab a 2-1 lead in the series.

Key again got the Game 3 nod, this time against the Orioles in the ALCS. Despite not losing in Baltimore during the regular season, the Yankees had to feel nervous facing three games in enemy territory after a David Wells gem in Game 2 leveled the series at a game apiece. It had to feel even more hopeless staring down arguably the best pitcher in the AL in Mike Mussina, and that despair likely deepened after Key surrendered a first inning two-run bomb to Todd Zeile on a hanging curveball. To his credit, Key made the adjustment, allowing just one more hit en route to an eight-inning, two-run masterpiece.

Mussina largely matched him stride for stride but melted down in the eighth as Jeter clubbed a two-out double and scored the tying run on a Williams single, who himself would score on a Tino double and Zeile throwing error before Cecil Fielder blew it open with a two-run blast. The game marked a death blow for the Orioles as the Yankees swept all three games at Camden to return to the Fall Classic for the first time since 1981.

The Yankees would soon learn that it would be no cake walk against the defending champion Braves and their three-headed rotation monster of Glavine, Maddux, and John Smoltz. Pettitte was shelled for seven runs in 2.1 innings while the Cy Young-bound Smoltz held the Bombers to one run in six innings in an ugly 12-1 Game 1 loss. That deficit widened to 0-2 with Key getting roughed up for four runs on ten hits in six innings while Maddux silenced the Bomber bats to the tune of eight shutout innings. To put it mildly, things were looking bleak staring down three games in Atlanta.

Williams took matters into his own hands the following game, driving in three runs including a two-run blast in the Yankees’ three-run eighth. At the same time, Cone outpitched the reigning World Series MVP, allowing one run in six innings to Glavine’s two. Rogers struggled in his debut season with New York and that only continued in Game 5, coughing up five runs in two-plus innings of work. The Yankees found themselves in a 6-0 hole through five, but cut that deficit in half in the sixth before Jim Leyritz clubbed a 2-2 Mark Wohlers slider to left for the game-tying three run blast and Wade Boggs drew the go-ahead bases loaded walk in the tenth. Pettitte avenged his Game 1 performance with 8.1 scoreless innings in Game 5, a fourth inning Fielder RBI double off Smoltz moving the Yankees to within one game of the ultimate prize.

Thus set up the defining moment of Key’s 15-year career as Torre handed the 35-year-old veteran the ball in the Yankees’ first World Series elimination game in almost two decades. He navigated around a Javy Lopez walk in the second and runners on second and third in the third to open the game with three scoreless, allowing his offense to spot him a three-run lead of Maddux, O’Neill leading off the third with a double and scoring on an unlikely RBI triple from Joe Girardi followed by RBI singles from Jeter and Bernie.

It was Key’s turn to sweat in the fourth, a Fred McGriff walk and singles from Lopez and Andruw Jones loading the bases with one out. Key walked Jermaine Dye on five pitches to surrender the Braves’ first run, but then made likely the biggest pitch of his life against Terry Pendleton. With the count 3-1 and nowhere to put the Braves’ DH, Key got Pendleton to roll over a perfectly located sinker right on the corner down and away, Jeter gathering to field the ball, step on second, and laser a throw to first for the inning-ending double play to strand the bases loaded and keep the Yankees’ 3-1 lead intact.

After facing the minimum in the fifth, Key surrendered a leadoff ground-rule double to Chipper Jones to bring former teammate and future Hall of Famer Fred McGriff to the plate, but Key got Crime Dog to ground out on what would be his final pitch for the Yankees. Torre replaced Key with David Weathers followed by Graeme Lloyd in a scoreless sixth. Mariano Rivera pitched a shutout seventh and eighth, allowing closer John Wetteland to collect a record-tying fourth save in a World Series en route to the Yankees’ 23rd championship.

Departure from Yankees and post-retirement

Key played two more big league seasons after his contract with the Yankees expired, signing a free agent deal with the Orioles prior to the 1997 season. He would make 59 appearances (45 starts) for Baltimore, pitching to a 3.64 ERA (122 ERA+) in 291.2 innings while narrowly missing out on a third World Series appearances as the Orioles were eliminated by Cleveland in the 1997 ALCS. As arm issues limited his availability in his second season with the Orioles, he officially called it quits following the 1998 season.

Since his retirement, Key has been inducted into the Clemson Hall of Fame and Alabama Sports Hall of Fame. He is an avid golfer, participating in amateur tournaments for over 15 years. He has passed on this love of golf to his son, James, who is a sophomore member of the Bucknell University Men’s Golf Team.

Key will never be cited as the best pitcher on most if not all the teams he played for across his 15-year big league career. However, he was exactly what those early-’90s Yankees needed — a veteran presence whose professionalism on the field spoke far louder than the quiet man ever would. In helping the team end its 14-year playoff drought and capture its first championship in 18 years, Key will forever be remembered by fans as one of the catalysts of the team’s most recent dynasty.

Staff rank: 95
Community rank: 88
Stats rank: N/A
2013 rank: 97


Baseball Reference



BR Bullpen

Pinstripe Alley

Curry, Jack. “Yankees Finally Get it Right and Land a Lefty.” New York Times, December 11, 1992.

Curry, Jack. “Jimmy and Cindy Key Are Co-Stars in ‘Honey, I Blew Up Your Salary’.” New York Times, January 24, 1993.

Curry, Jack. “Jimmy Key: The Man in Control.” New York Times, June 26, 1994.

Heyman, Jon. “While Key Pitches, His Wife Controls Money in Family.” Los Angeles Times, August 4, 1993.

Hennessy, Brian. Nine Former Greats to be Inducted into Clemson Hall of Fame.

McFarland, Joe. “Key to the Game.” Alberta Dugout Stories, April 22, 2022.

Glew, Kevin. “Nine Things You Might Not Know About... Jimmy Key.” Cooperstowners in Canada.

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