Chicago Cubs: Ranking the team’s 3 worst trades of the last 50 years

No matter which team you root for, there are some trades in history that just didn’t break your way – and the Chicago Cubs are no exception. The one everyone constantly points to is the Lou Brock deal, and rightfully so. Brock went on to win a pair of World Series rings and amass over 2,700 hits in a Cardinals uniform while hitting a scorching .334 against his former team over the next 16 seasons.

Every generation of fan has that one trade they just can’t get over – or in some instances, there are more than one. But I took a crack at singling out 3 trades that stand out above the rest, including one that might be too soon to judge, but is still worth calling out given the events of recent years.

Cubs: 3 worst trades of the last 50 years: #3 – DJ LeMahieu heads to Colorado in the ill-fated trade that netted Ian Stewart

Theo Epstein largely gets a pass given he was the architect of the first Cubs World Series team in more than a century, but one of the first moves of his tenure is one that only looks worse with time.

Chicago sent infielder DJ LeMahieu and outfielder Tyler Colvin to the Rockies in exchange for Ian Stewart and reliever Casey Weathers. Colvin had never been the same since his freak injury, unable to recapture any semblance of power and, to that point, LeMahieu showed no signs of being anything remarkable.

However, since that trade, LeMahieu has won a pair of Silver Sluggers, two batting titles and three Gold Gloves while batting .301 with a .357 OBP with the Rockies and Yankees. Thinking of his bat-to-ball skills ahead of the likes of the Cubs’ core is enough to prompt some wild fantasies. Instead, we got Stewart, who put the team on blast and was shown the door mid-season back in 2013.