3. July 21, 1988: Ken Phelps for Jay Buhner
I got a lot of problems with you people.
Years before George Steinbrenner was on Frank Costanza's couch explaining that his son had likely passed away, while also justifying this deal by saying his people loved Ken Phelps' bat, the Yankees once again believed they were swapping out the right young talent for a veteran leader. Wrong-o.
Buhner certainly prevailed in the Feats of Strength, and Phelps' career was done by 1990. He spent half of both 1988 and 1989 in the Bronx, actually posting an .890 OPS in 35 successful games immediately after the trade. The next season, he slowed down, with a .718 mark in 86 games before he ended up in Oakland and regressed further into retirement.
Phelps' "bat" made noise like Steinbrenner was promised for about 30 games, but Buhner left Big Stein wearing the bucket, hitting 40 homers annually from 1995-1997. He might've been a great addition to some early-90s Yankee teams that were a few pieces away from being truly competitive (1993, for example).
Hey, maybe without this brutal trade, the Yankees ultimately never swap Roberto Kelly for Paul O'Neill, though, a silver lining if there ever was one. Still, Steinbrenner got swindled, much the same way he did when he mistook a burning jacket placed in front of the vent for the smell of delicious calzones.