10 worst trades in New York Yankees franchise history

8. Kevin Brown Acquired for Jeff Weaver, Brandon Weeden, Yhency Brazoban and Cash, 2003

Realizing Jeff Weaver was not the consistent starter they longed for, the Yankees traded Weaver and others to the Los Angeles Dodgers for Kevin Brown. This made a bad situation worse.

Brown had pitched the previous five seasons with the Dodgers. ending 2003 with a 2.39 ERA. But the good performances were rumored to have been helped by performance enhancing drugs.

In fact, the famous Mitchell Report named Kevin Brown as a user of PEDs during his time in with the Dodgers.

His performance with the Yankees showed that report to be accurate. In his final year in Los Angeles, hitters had a .236 batting average against Brown. This number rose to .262 in 2004 and .341 in 2005 with the Yankees. Of course, his 2004 season was marred by a shattered hand after Brown punched a dugout phone, which is always what you want to see in a major acquisition, as well as the Game 7 bomb he dropped in a last-ditch attempt to hold off the charging Red Sox.

Another interesting player in this trade was Brandon Weeden. Weeden eventually retired from baseball and became a quarterback for Oklahoma State University. He was then drafted by the Cleveland Browns 22nd overall. He turned 30 before his rookie season in the NFL. Sadly, he lacked the basic fundamentals necessary to compete in the NFL. His signature moment for the Browns was getting caught under the American flag pregame.

Weeden did ultimately escape from under the flag, but his career never recovered. The Yankees did find a redeeming moment in this trade by shipping him out.  But the next trade on our list was so horrific that it should have been a crime.