-The Red Sox Trade Babe Ruth to the Yankees for Cash
Okay, so this wasn’t exactly a trade, but it was probably the most famous transaction of baseball history. With Babe Ruth demanding more money and the Red Sox not wanted to pay it (owner Arthur Franzee also needed funding for some of this Broadway plays), the team sold Ruth to the Yankees for 125,000 in cash and a 300,000 loan in 1919. You can safely say that the two teams went in opposite directions, with the Yankees winning 28 World Series since and the Red Sox taking over eight decades to get to another one. And Ruth, well, he became a pretty decent player.

-The Lakers Trade Shaquielle O’Neal to Miami Heat for Caron Butler, Lamar Odom, Brian Grant and a future first-round draft choice
O’Neal apparently didn’t want to play for the Lakers anymore. Fine. What makes this trade so mind boggling is that the Lakers were willing to break up a team that had just gone to the NBA Finals and could have easily won three of four more titles (they had already won three previous one with virtually the same team). While it made no sense at the time, it worked out for both teams as the Heat won a title in 2006 and the Lakers have one two straight coming into this season.

-The Dallas Cowboys Trade Herschel Walker and Four Draft Picks to the Minnesota Vikings for Jesse Solomon, David Howard, Isaac Holt and Eight Draft Picks Over Three Years
So what do you get in return for an aging running back who never had another quality season in the NFL? How about draft picks that turn out to be Emmitt Smith, Russell Maryland, Kevin Smith, Darren Woodson and Clayton Holmes, which lead your team to three Super Bowls. Maybe hindsight is 20/20 but from a sheer talent standpoint, this trade was mind boggling.