The Absolute Worst Trades in Chicago Cubs History
By Jerry Trotta
It goes without saying that the Chicago Cubs are one of the MLB's most storied franchises even though they only have two world championships to show for it. Most of the club's misfortunes are simply due to the fact that it almost always faltered on the big stage.
A healthy chunk of Chicago's woes, however, can be traced back to some egregious decisions in the front office, particularly on the trade front. Since we're without baseball for the foreseeable future, let's do a deep dive into some of the worst deals in Cubbies history.
5. Dealing Josh Donaldson to Oakland, 2008
In another laughable example of Chicago giving up on young talent, the organization traded Josh Donaldson, Sean Gallagher and Matt Murton to the Athletics for Rich Harden and Chad Gaudin. Donaldson, of course, went on to become a perennial All-Star and win the AL MVP award with Toronto in 2015. Oh, Donaldson is still playing while Gaudin and Harden have been out of the league since 2013 and 2011, respectively.
4. DJ LeMahieu and Tyler Colvin to Colorado for Ian Stewart and Casey Weathers, 2011
Imagine the Cubs having DJ LeMahieu's clutch gene to bail them out in the postseason in recent years? Instead, Chicago inexplicably bailed on DJ at a young age in 2011 and dealt him alongside Tyler Colvin to the Rockies in exchange for Ian Stewart and minor leaguer Casey Weathers. LeMahieu, as we know, is one of the game's most established hitters. Stewart, meanwhile, spent one season in the Windy City, during which he played just 55 games and hit .201/.222/.382.
3. Lee Smith to Boston for Al Nipper and Calvin Schiraldi, 1987
Jim Frey's first trade as general manager for the Cubs was a disaster. While Chicago was still highly competitive, Frey sanctioned a trade that offloaded stud reliever Lee Smith. The Hall of Famer earned five more All-Star selections and finished in the top five of Cy Young voting on three separate occasions.
2. Lou Brock to the Cardinals, 1964
Not only did the Cubs trade a Hall of Famer in Lou Brock, but they traded him to the Cardinals, the team's most bitter rival. After the deal, Brock went on to hold the all-time stolen base record until Ricky Henderson shattered his mark. In 1974, Brock set the MLB record for stolen bases recorded in a single season with 118. That feat was also surpassed by Henderson. The Cardinals rightfully retired his No. 20 jersey and inducted him into the team's Hall of Fame.
1. Trading Dennis Eckersley to Oakland, 1987
This wasn't so much bad business as bad luck, but it still qualifies. In 1987, the Cubbies dealt Dennis Eckersley to the Athletics and he subsequently blossomed into a Hall of Famer. He won the AL MVP in 1992, the Cy Young in 1992, the ALCS MVP in 1988, was a two-time Reliever of the Year, and was enshrined in the Hall of Fame. What an absolute atrocity of a trade for Chicago. It deserves to take the cake here.