Ian Stewart 3B- Foul Tip
This one requires a bit of extra digging to understand why this player means anything to the Cubs. He was ranked as highly as the number two prospect in baseball in 2005, so when the Cubs traded for him in 2012 some of his prospect shine had faded.
However, there was still hope. This was the first relatively important deal of the Epstein/Hoyer regime and it saw the Cubs try to help Stewart regain his footing on a rebuilding team in return for a relatively unknown soft-hitting middle infield prospect named DJ LeMahieu.
Epstein didn’t make many deals that ended up looking bad in the long run but this is definitely one of them. LeMahieu would go on to be worth 31.5 WAR over his 13-year MLB career (that’s still going), whereas Stewart would only play one season (55 games) for the Cubs in 2012 and only 24 more games in his career for the Angels in 2014.
That being said, if the Cubs had kept LeMahieu there’s nothing that says that the Cubs would subsequently make the trade for Addison Russell, or have a poor enough season to draft Kris Bryant or Kyle Schwarber (who we’ll hear about again later).
While this trade looks awful on paper, in baseball everything happens for a reason.