Thinking Back on the Very First Trade of the Theo Epstein Era - It Was Not Good

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Thinking Back on the Very First Trade of the Theo Epstein Era – It Was Not Good

Chicago Cubs

On the whole, the Theo Epstein era of the Chicago Cubs was a success. That’s obvious, right?

We could go through the litany of individual moves that worked out – some of them outrageously outsized successes – or we could point to the five postseason appearances in nine years, the three NL Central titles, the three NLCS appearances, or the World Series win.

But it’s also fun(?) to look back on some of the clunkers. Every organization has them, and with the benefit of hindsight, the ones that are REALLY bad stand out for just how silly they now seem.

Incidentally, in a few weeks we’ll be at the anniversary of Epstein’s first trade as the President of Baseball Operations for the Chicago Cubs, and it may actually have been his worst. Getting the bad ones out of the way early, eh:

It isn’t just that Stewart didn’t work out, it’s that the Cubs decided to keep him for another season after it clearly wasn’t working, a decision that wound up later seeing Stewart dumped because of some late-night tweets. There were red flags even before the trade, but the Cubs – knowing they were rebuilding – wanted to take a big swing on controlled upside. Whiff:

(via FanGraphs)

And, of course, it was a whiff to include D.J. LeMahieu in the deal, which seems like a matter of not taking the time to really know what you had in the guy. Maybe he doesn’t become quite what he did with the Rockies, but any concerns that he was too big to play quality second base or wouldn’t succeed offensively without power were clearly mistaken. (That said, it’s only fair to point out the LeMahieu didn’t actually start to hit much until 2015, his FOURTH year with the Rockies.)

For what it’s worth, if you want to reminisce to the downside, Sahadev Sharma and Patrick Mooney looked at the other worst moves of the Epstein era here (well, and best moves, too, but you already know all about those). Not getting Justin Verlander in 2017 will always stick out as a big one, given how much he wanted to come to the Cubs, and how obscenely well he pitched thereafter for the eventual World Champion Astros. There’s no telling what might have been if the Cubs had grabbed him.

Other moves that come to mind: the Edwin Jackson signing, not trading more of the core earlier on, some big draft pick whiffs (every org has those, though). Ultimately, there haven’t been *THAT* many totally disastrous moves/non-moves. And the worst one by far was the very first one. So that seems pretty decent.

Anyway. I just thought this was some backwards fun for your Saturday afternoon, the day after Epstein’s departure.

(Photo by Jonathan Daniel/Getty Images)

Author: Brett Taylor

Brett Taylor is the Editor and Lead Cubs Writer at Bleacher Nation, and you can find him on Twitter at @BleacherNation and @Brett_A_Taylor.