Jimmy Key Helped Turn Mid-90s Yankees Into Champions

By Sal Maiorana

May 8, 2024

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Sal Maiorana, a friend of the site, shares some of his thoughts on the Yankees.

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George Steinbrenner was supposed to be banned for life in 1990 from partaking in the day-to-day operations of the Yankees after he was found to have paid shady gambler Howie Spira to dig up dirt on Dave Winfield.

But after just 2 ½ years, baseball commissioner Fay Vincent reversed course and lifted the punishment before the 1993 season, and upon his return Steinbrenner wasted no time jumping right back into the running of the team and planned to come out guns blazing in free agency.

The Yankees finished the 1992 season 10 games under .500, their fourth straight losing record and 11th consecutive year of missing the postseason, just an appalling situation for Steinbrenner who was obviously paying attention and privately gritting his teeth during his exile.

The free agent class was loaded, and Steinbrenner was convinced he would be able to acquire the necessary big-name pieces to end the Yankees misery. Instead, he dealt mostly with rejection, particularly from outfielder Barry Bonds and pitcher Greg Maddux who he made lavish offers to, but also from pitchers Doug Drabek, David Cone, Jose Guzman and Greg Swindell, and position players Kirby Puckett, and Mark McGwire among others.

Rejection, especially those turning down his money, was not something Steinbrenner was accustomed to, but he shrugged his shoulders and said, “We’ll find a way to win without them.”

And it turned out that he was right because two players who did take George’s money - 35-year-old third baseman and future Hall of Famer Wade Boggs, and 32-year-old left-handed pitcher Jimmy Key - went on to eventually help the Yankees end their franchise-record 18-year championship drought.

General manager Gene Michael - who during Steinbrenner’s time in purgatory had begun rebuilding the franchise by getting players into the farm system like Derek Jeter, Andy Pettitte, Jorge Posada, Bernie Williams and Mariano Rivera - had to sell Steinbrenner on Key, though.

He pointed out that in nine seasons with the Blue Jays, Key had pitched to a 3.42 ERA and a 1.196 WHIP, and in 1987 he was runner-up to Roger Clemens in the Cy Young balloting when he led MLB in ERA (2.76) and WHIP (1.057). He had also performed in four postseasons for Toronto including 1992 when he was the winning pitcher in two World Series game as the Blue Jays defeated the Braves for their first championship. Oh, and he’d also gone 8-1 against the Yankees at Yankee Stadium.

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.”

That might have been a stretch with a guy like Maddux, another future Hall of Famer, out there on the market, but his point was that Key was always around the strike zone and would be a nice alternative signing.

“You can’t dwell on Bonds or Maddux or Cone,” Yankees manager Buck Showalter said the day Key signed Steinbrenner’s four-year, $17 million offer. “If one part of the equation doesn’t work out, then you move on to the next part. I’m excited about getting a player of his background and with his track record coming to New York. As important as that is, I’m excited that he wanted to come to play in New York.”

Showalter’s point about Key wanting to perform on the big stage in New York was important. There were some who believed that Key, who had pitched in relative obscurity up in hockey-crazed Canada, would not hold up under the bright lights of New York. He always laughed at that.

“The thing I couldn’t understand is that people couldn’t see me pitching here,” Key said. “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.

“I’ve been in clubhouses for nine years and I know some guys have reservations about New York. Some guys are looking for a comfortable place to play so that when you mess up, nobody gets on you. The good thing about New York is when you do play well, everybody is on your side.”

It did not make for the big offseason splash Steinbrenner had hoped for, and the turnaround of the Yankees’ fortunes did not begin immediately, but by the time Key’s four seasons in pinstripes were complete, the Yankees won the 1996 World Series and he was an integral reason.

He went 18-6 with a 3.00 ERA in 1993 when the Yankees took their first step toward their return to relevance with an 88-74 record. In 1994 when the strike ended the season the Yankees had the best record in the AL at 70-43 and Key was 17-4 with a 3.27 ERA and finished second to Cone in the Cy Young vote.

In 1995, the year the Yankees ended their playoff drought with a wild-card appearance, Key missed almost the entire season due to a rotator cuff injury, but he returned in 1996 and while he was starting to show signs of decline, he made 30 starts and picked up the slack when Cone, who had joined the Yankees in 1995, missed four months with an aneurysm in his shoulder.

Key started Game 3 of the 1996 divisional sweep against the Rangers, and Game 3 of the ALCS triumph over the Orioles - “Jimmy Key was spectacular,” Joe Torre said that night. He was cuffed around by the Braves in Game 2 of the World Series, but then was the winner in Game 6 when the Yankees completed their rally from two games down to win their first championship since 1978. Oh, and the Braves’ starter in Game 6? Greg Maddux.

The Yankees won three of Key’s four starts that postseason and he pitched 24.1 innings to a 3.33 ERA, a fitting end to his time in the Big Apple. That offseason, the Yankees put forth a weak attempt to re-sign Key and he wound up with the rival Orioles, and there was no small amount of criticism that they received.

“They looked at this as a business decision,” Key said of the Yankees’ front office, who ultimately replaced him with Orioles free agent David Wells. “This is the way the game is these days. Players move. It was my time to move again.”

Torre, who would go on to have a frosty relationship with Wells, sounded a warning sign almost as soon as the two players switched uniforms. “I’m partial to the guys who were on the club last year, especially Jimmy Key,” he said. “Jimmy Key proved he can win in the postseason. We’ll see if David Wells can do that.”

Key was terrific for the Orioles in 1997, 16-7 with a 3.43 ERA, then declined in 1998, after which he retired with a career record of 186-117, a 3.51 ERA and a 1.229 WHIP.