Chicago Cubs: This trade was years in the making for Theo Epstein

The Chicago Cubs finished last in the NL Central for the first three years of Theo Epstein’s tenure in Chicago. If it’s possible to say it was “calculated”, that may have been the case. After years of building through losing, the trade for Aroldis Chapman was about winning–and has been a long time coming.

When the Chicago Cubs hired Theo Epstein in October of 2011 to be the President of baseball operations, many fans had high hopes after what the young executive had accomplished in Boston–ending the 86-year drought and bringing a World Series to Beantown. One of the first things Epstein talked about was “the plan”.

The plan was a similar blueprint to what they had used in Boston to win a title in 2004 and then again in 2007. No, it might not be “original”, but I’m pretty sure the fans around Chicago aren’t going to mind. The team began to focus on player development. Grooming players through their own system. While that process was underway the Cubs started dealing players who put up solid first half numbers for young prospects to add to the bunch.

The sign-and-flip has been one of the Cubs’ signature moves over the past four years. The first was Paul Maholm and then Ryan Dempster. Maholm netted Arodys Vizcaino, who made a brief cameo but has since been traded back to the Braves. Dempster to the Rangers garnered a couple of young prospects–a RHP named Kyle Hendricks and INF Christian Villanueva.

More from Cubbies Crib

• Cubs: P.J. Higgins deserves to be in the lineup on a daily basis
• Cubs might start to limit Justin Steele’s workload soon
• Cubs: Adrian Sampson is forcing his way into the conversation
• Projecting the Chicago Cubs bullpen to open the 2023 season
• Cubs fans are beginning to see the light at the end of the tunnel

Later they dealt Scott Feldman to the Orioles for Jake Arrieta and Pedro Strop. Jason Hammel and Jeff Samardzija were sent to Oakland for Addison Russell and Billy McKinney. He also sent the onetime poster boy for the Cubs, Starlin Castro to the Yankees for Adam Warren. Hammel returned this year via free agency while McKinney and Warren were two of the players dealt to get to the focus of this article. The acquisition of Aroldis Chapman.

Chapman came in with some baggage, but this isn’t the post for that. If you’re interested you can check out these two posts on Chapman in defense of him and against him. This is about the path that the Cubs have taken to finally get to this point. To the moment of making that trade that would help them crush 100+ years of misery. Did Epstein know this was coming all along? Not specifically for Chapman–but a trade of this magnitude he did.

For three years the Cubs were sellers. The deadline was about getting the most out of what they had and building for the future. Last year, with the Cubs on the verge of pushing through, many felt a blockbuster move was coming. But it never did. The Cubs acquired Dan Haren and Tommy Hunter, neither of which had any bearing on the Cubs second half run which ended with a trip to the NLCS.

As fans, we watch the trade deadline and wonder what teams are willing to do to get “over the top”. The Cubs paid a price. But for much of the last four years they’ve been schooling teams in how to take advantage of the trade market. The Cubs acquired many of the young players they have now and developed them into All-Stars. They’ve drafted some of the best pure hitters over the past few drafts (Kris Bryant, Kyle Schwarber, Ian Happ), showing they can grow their own prospects as well.

But now was the time. The Cubs had the assets to make the deal, and are in a position to make a deep run into the playoffs–hopefully ending at Wrigley Field on a late October night with one final “W”. There were a lot of ups and down, plenty of heartache (there’s only so much positivity in three last place finishes), but now they’re within reach. As Theo said, “If not now, when?”.

Next: Are the Cubs done making trades?

The hope is that question is not a closed ended one. That the Cubs will have the ability to ask it again next year, and the year after that. And possibly the year after that one. But it was a long time coming to be able to even ask the question.