Worst Trades in Yankees History

The New York Yankees are one of MLB's most legendary franchises, hoisting the World Series trophy at the end of 27 different seasons. However, that doesn't mean they've always taken the easy road to get there -- far from it, in fact.

Sometimes, New York's championship seasons have been boosted by brilliant maneuvers and three-dimensional chess. Other times? They've won in spite of their own mistakes, needlessly gutting their farm system and betting on clear blunders. This article? It's about the failures.

6. Juan Rivera, Nick Johnson and Randy Choate for Javier Vazquez, 2004

This would've been a blunder no matter who the Yankees were surrendering, but giving up two productive players in Rivera (who was a thorn in their side in Anaheim) and Johnson hurt, too. Vazquez lost all his shine when he hit the AL East, registering a 4.91 ERA in the Bronx after boasting a 3.24 ERA and 241 Ks in 2003. He was part of a beleaguered staff that helped blow the 2004 ALCS to Boston. Somehow, the NYY didn't learn their lesson here -- they reacquired Vazquez for Melky Cabrera after a top-five Cy Young season for Atlanta in 2009, and he was...terrible again, posting a 5.32 mark in his inglorious return.

5. Doug Drabek for Rick Rhoden, 1986

Doug Drabek reached the majors with the Yankees in 1986 after fighting his way through the ranks, but he was dealt for veteran Rick Rhoden in a six-man trade following the campaign, and immediately became a Cy Young contender. Drabek won the Cy in 1990, a time when the Yanks...really could've used a stable young arm. Rhoden? He was done by '88, and helped some non-competitive Yankee teams...not compete.

4. Mike Lowell to the Marlins, 1999

Mike Lowell was a Yankee before he tormented them in two different spots. Jettisoned because...well, because Scott Brosius was better than expected in 1998, Lowell went to the Marlins, where he blossomed into an All-Star and defeated the Yankees in the 2003 World Series. He was eventually traded again...with Josh Beckett to the Red Sox, and tortured New York some more, serving as a veteran leader and capturing the '07 title, too. His grit would've fit well in New York. We love Brosius, but there was enough room for the both of 'em.

3. Willie McGee for Bob Sykes, 1981

The spark plug who made the '80s Cardinals go? Yeah, it would've been nice for the Yankees to have kept him. Four years after Willie McGee was their first-round pick (15th overall), they shipped him out to the Cards for Bob Sykes, who never appeared in the bigs again, and who's difficult to find on Google, usurped by an Alabama BBQ restaurant. McGee was the 1985 MVP, stole 40 bags a year for the early part of the decade, and would've fit nicely alongside Rickey Henderson in New York.

2. Jay Buhner for Ken Phelps, 1988

The Yankees spent the '90s being tormented by Buhner in Seattle. Jay was truly bad to the Bone, drilling over 40 homers a year from 1995-1997. But back when he was a bit less intimidating (no skulled-out look or goatee), he was a Yankee farmhand, and was traded to the M's in 1988 for Ken Phelps, who couldn't hit .250 in pinstripes and was sent away in a deal midway through the next season. This is the trade that made Frank Costanza the most upset of all.

1. Fred McGriff to the Blue Jays, 1982

The Yankees of the '80s trading away a vaunted prospect just because George Steinbrenner felt like it? No way. The Yanks traded McGriff (and valuable pitcher Mike Morgan) to Toronto, within their own division, just one year after they drafted him, receiving nothing of note in return. McGriff hit .272 with nine homers and 41 RBI in rookie league ball for the Yanks in '82, but never advanced further. Of course, he hit 493 round-trippers in the bigs, and owned the early '90s with the Braves. Would've been nice to have him at first in Don Mattingly's twilight years.