15 worst trades in New York Yankees history

New York Yankees v Toronto Blue Jays
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7. July 5, 2002: Yankees Trade Ted Lilly, Add Jeff Weaver in Three-Team Whirlwind

Tons of interesting players changed hands in this one! The Yankees received none of them. When the dust settled, the Detroit Tigers had added future rotation stalwart Jeremy Bonderman and eventual '08 Rays masher Carlos Peña, while the Oakland A's had secured eventual All-Star left-hander Ted Lilly. The Yankees? They had Jeff Weaver, whose long, flowing locks never quite fit in in the Bronx.

Weaver, another member of the somehow-never-ending club of pitchers from small-market teams who the Yankees believed had another level to their games, flamed out in the Boogie Down, too. He posted a 4.04 ERA in 15 games post-trade in 2002, but put up a 6.75 ERA in two outings in a five-game ALDS defeat at the hands of the Angels.

2003? Weaver went 7-9 with a 5.99 ERA. Absurdly garish today, but somehow, the Yankees had one of these guys on the staff every season from 2002-2011. He was given one, singular playoff appearance, stepping into the bottom of the 11th of Game 4 of the World Series in Miami. Somehow, Joe Torre got it to work! He retired Jeff Conine, Lowell, and Derek Lee in order to preserve the tie! Wow!

Then, the first batter of the 12th, Alex Gonzalez, walked him off and flipped the series. Can't win 'em all. Lilly, who posted a 4.34 ERA in Oakland that summer and was one year away from his first All-Star appearance, probably wouldn't have done that.