Chicago Cubs: Best deadline trades during the Theo Epstein regime

The Chicago Cubs’ Theo Epstein has been on both ends of the deadline. Previously as sellers, and now as buyers. But each deadline deal had importance to the Cubs in some form. We look at the deadline moves he’s made over the past six years.

There have been trades that have happened outside of the deadline, but those won’t count here. We’re looking at the Chicago Cubs moves at the trade deadline (and a little before) to see just how important the moves that Theo Epstein & Co. made were. Whether looking to the future or going all in now, Epstein has done an excellent job of putting the team in fantastic position to succeed.

had shown will take us back to the beginning–or “the before time”–of Cubs baseball. Epstein inherited a team that was less than impressive on the field, and even worse on the team’s checkbook. So Epstein went to work each deadline to change the focus of this Cubs team. From “lovable losers” to a borderline dynasty, Epstein has hit on more than he’s missed with the deadline deals he’s made.

Let’s take a look at what he’s done in his time in Chicago, and why this might only be the beginning of this list.