We've done the best Cubs trades of the past 50 years, now let's do the worst. In some ways, this list was tougher, not because there weren't enough bad trades but because there were too many. I could have limited this list to just 11 terrible deals like last time, but that would have meant leaving a few off the list that really irked me at the time. So I gave up trying to pare down the list and went with an unlucky 13 with one honorable mention. The Lou Brock deal is often singled out as the Cubs worst trade, but I consider the Lee Smith trade to be even worse. It's bad enough that they turned down a far better deal involving a future Cy Young pitcher (whom I'll reveal later), but they turned around and accepted a terrible offer from the Red Sox instead. In the long term view, the Smith deal would also spur a series of unfortunate events that would set the Cubs back for a decade. Two things to note as you read through the captions in the gallery:
1) Note how many times the Oakland A's seem to be involved when it comes to making great players out of Ex-Cubs.
2) Note the love/hate relationship the Cubs have had with relief pitchers. They oscillated between trading good young players for washed up relievers and trading young, talented relief pitchers for journeymen. Whether it was love or hate, however, one thing was consistent: The Cubs always seemed to wind up on the wrong end of the trade. Perhaps when it came to making trades involving relievers, the Cubs would have been wise to follow the George Costanza formula for success -- Do the complete opposite of your instincts.
In the interest of brevity, I've left out a couple of throw-ins who didn't make an impact one way or the other, but the principle players are all mentioned in the list.
This list is not for the faint of heart....