15 worst trades in New York Yankees history

New York Yankees v Toronto Blue Jays
New York Yankees v Toronto Blue Jays / Abelimages/GettyImages
1 of 15

The New York Yankees have long been hesitant to trade top prospects for help that can get them over the World Series hump. Perhaps it's because they're ... bad at it?

The unfortunate reality is that, no matter how many Ls you've taken on the trade market, dealing prospects for impact talent is basically always the right way to go -- as long as you've scouted your impact talent properly. The Yankees can't let their recent rear-view mistakes dissuade them from continuing to push towards a title ... but they've still let their issues compound recently, chasing a lopsided deal with another false idol.

Notice how none of these stinkers are from the Yankees' heyday in the '40s, '50s and '60s? Back then, the Yankees seemingly won every trade, from the Don Larsen swap with the Orioles to the Roger Maris plunder to any one of the hundreds of successful deals they pulled off with the Kansas City A's.

Now? The rest of MLB has caught up, and they've figured out the Yankees will -- 9 times out of 10 -- pick the wrong prospects to protect. Exaggerating. Sort of.

Of all the Yankees' big swings, these are the 15 that worked out the worst.

15 Worst New York Yankees Trades of All Time

15. Dec. 13, 2003: Yankees Acquire Kevin Brown('s Contract) for Jeff Weaver, Yhency Brazoban, Brandon Weeden

Immediately after falling to the Yankees in the 1998 World Series, Kevin Brown traded Padres brown for Dodger Blue, signing a free agent contract that helped redefine the pitching market in the years that followed. His seven-year, $105 million deal made him the still-unexpected answer to a trivia question as baseball's first $100 million man.

Fittingly, he spent Years 6 and 7 of that deal with the Yankees after performing quite well in three 200+-inning years with the Dodgers, dominating in a fourth shortened season, and basically losing 2002 to injury.

At the age of 39 in 2004, Brown managed a 10-6 record with a 4.09 ERA in 132 innings. Nearly overnight, he aged out of inducing swings and misses (83 Ks, 132 hits allowed), and poisoned his solid numbers by becoming infamous in pinstripes. He punched a clubhouse wall with his left hand in September, breaking bones down to the wrist, but was able to make it back for the postseason. Kind of a bigger bummer! He finished off the Yankees' 2004 collapse with two horrific starts including a Game 7 clunker, allowing 9 runs in 3.1 innings. He retired after 13 more troubled starts in 2005, making this a bad trade no matter what the Bombers had surrendered.