Don Mattingly: 1991-1995
The first modern-era Yankee to be regularly referred to as The Captain, Mattingly held the title during one of the worst down years in franchise history in 1991, a 71-win campaign led by Stump Merrill.
Prior to the 1992 season, Buck Showalter was hired and things began to turn, with Mattingly building ever-so-subtly towards the first postseason appearance of his remarkable career.
The '92 Yankees won 76 games, and they won 'em for Mattingly. In 1993, they acquired Paul O'Neill, signed Wade Boggs, and reached 88 wins, falling seven games short of the Toronto Blue Jays -- but they would've won the AL Wild Card by one game if that honor had existed back then.
In 1994, Mattingly's Yankees surged toward the postseason as he attempted to fend off his bodily breakdown, but the strike sliced the season at the worst possible point, with New York sitting at 70-43 and leading the AL East.
1995 was Mattingly's final season, his first playoff appearance (!), and ... arguably the team's worst postseason ending, non-2004 division. They surrendered a 2-0 series lead and a late lead in Game 5 on the road in Seattle in the ALDS, and though it shattered The Captain (and David Cone, who felt responsible), it led only to better things for the storied franchise.