New York Yankees 1982 1995

The New York Yankees 1982–1995 Captain Don Mattingly

Following the team's loss to the Dodgers in the 1981 World Series, the Yankees had their longest absence from the playoffs since 1921. The Yankees of the 1980s, led by All-Star first baseman Don Mattingly, had the most total wins of any major league team but failed to win a World Series. They consistently had a powerful offense; Mattingly at various times was teammate to Dave Winfield, Rickey Henderson, Mike Pagliarulo, Steve Sax, and Jesse Barfield, but the starting pitching rarely matched the team's performance at the plate. After posting a 22–6 record in 1985, arm problems caught up with Ron Guidry, and his performance declined in the next three years.

The team came close to winning the AL East in 1985 and 1986, finishing second to the Toronto Blue Jays and Boston Red Sox respectively, but fell to fourth place in 1987 and fifth in 1988, despite having mid-season leads in the AL East standings both years. Despite their lack of championships and playoff appearances the Yankees posted the highest winning percentage of all MLB teams during the 1980s.

By the end of the decade, the Yankees' offense was on the decline. Henderson and Pagliarulo had departed by the middle of 1989, while back problems hampered both Winfield and Mattingly. Winfield's tenure with the team ended when he was dealt to the Angels.

From 1989 to 1992, the team had a losing record, spending significant money on free-agents and draft picks who did not live up to expectations. In 1990, the Yankees had the worst record in the American League, and their first last-place finish since 1966.

The poor showings in the 1980s and 1990s would soon change. Steinbrenner hired Howard Spira to uncover damaging information on Winfield and was subsequently suspended from day-to-day team operations by Commissioner Fay Vincent when the plot was revealed. This turn of events allowed management to implement a coherent acquisition/development program without owner interference. General Manager Gene Michael, along with manager Buck Showalter, shifted the club's emphasis from high-priced acquisitions to developing talent through the farm system. This new philosophy developed key players such as outfielder Bernie Williams, shortstop Derek Jeter, catcher Jorge Posada, and pitchers Andy Pettitte and Mariano Rivera. The first significant success came in 1994, when the Yankees had the best record in the AL, but the strike ended the season and Mattingly's best chance for a World Series title.

A year later, the team qualified for the playoffs in the new wild card slot in the strike shortened 1995 season, their last prior playoff appearance occurred in a strike shortened year. In the memorable 1995 American League Division Series against the Seattle Mariners, the Yankees won the first two games at home and dropped the next three in Seattle. Mattingly, suffering greatly from his back injury, retired after the 1995 season. He had the unfortunate distinction of beginning and ending his career on years bookended by Yankee World Series appearances (1981 and 1996).