15 worst trades in New York Yankees history

New York Yankees v Toronto Blue Jays
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6. Nov. 26, 1986: Yankees Trade Doug Drabek for Pirates Package

We're now entering the "1980s Yankees Pull the Plug on a Prospect Too Quickly" portion of the list, starring future 1990 Cy Young winner Doug Drabek in the No. 6 spot.

Following the '86 season, the Yankees sacrificed Drabek in a package meant to acquire Pirates veteran hurler Rick Rhoden. Rhoden had made the All-Star team and finished fifth in the Cy Young chase in '86, and was actually (clears throat) solid in the Bronx! He went 16-10 with a 3.86 ERA in 1987 with the Bombers, but was unable to overcome Steve Trout's stink, as the team again missed the playoffs. Rhoden was solid again in '88 before being dealt to Houston and finishing his career there in 1989.

Drabek? He leveled up almost immediately in the 'Burgh. The next four seasons were like an incline pyramid:

1987: 11-12, 3.88 ERA, 176.1 innings
1988: 15-7, 3.08 ERA, 219.1 innings
1989: 14-12, 2.80 ERA, 244.1 innings
1990: 22-6, 2.76 ERA, 231.1 innings, Cy Young Award

Honestly? He didn't hit the downward slope until 1995 with the Astros. It would've been very nice for some of the worst teams in Yankee history to have Drabek fronting their rotations during the dead years. Particularly ironic that he got much worse in '95, though, just as the Yankees were ascending. His struggles probably prevented the Yankees from trading for him at that year's deadline and absorbing his late-career implosion.