Chicago Cubs: What’s been Theo Epstein’s best trade?

It’s been a successful five-year tenure in Chicago for Theo Epstein and his crew. Epstein has made many trades, and many of these trades have helped shape the team into what it is today.

We know about the trades for Miguel Montero, Dexter Fowler, and Justin Grimm. Grimm and Carl Edwards, Jr. were both acquired together for Matt Garza. Let us not forget about the trade for Kyle Hendricks, coming over from the Rangers for Ryan Dempster, in 2013.

Or this year, when they acquired a young, cost-controlled arm in Mike Montgomery, who can be a swing man between the bullpen, and the rotation.

Montgomery has experience doing both, as he was a starter in the minor leagues for the Royals and the Rays. Once the Mariners acquired him, they turned him into a reliever, and it’s worked well.

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The thing about rebuilds is that they take a little bit of everything, meaning good drafting, making good acquisitions in free agency, and making trades that acquire young, impactful players, all to build up a strong farm system, where the young players can develop until they are ready for the big leagues.

The Cubs have done that very thing. Not to mention, they’re farm system is still very strong to this day. They are still looking to make trades before this year’s August 1st trade deadline, mostly for young, cost-controlled pitching. Jayson Stark mentioned a possible match with the Rays.

With newly acquire Aroldis Chapman joining the team, it’s time to sit down and examine which trades have been Epstein’s best, most impactful trades?

Next: Cubs find their ace, bullpen horse