When Theo Epstein took over as President of Baseball Operations for the Chicago Cubs in 2011 he immediately indicated the desire to build a consistently competitive and healthy organization both in the bigs and throughout the minor leagues.

Epstein vowed to develop “a foundation of sustained success.” 

Cubs fans were elated. For the first time in what seemed like forever they had an owner that appeared to be concerned as much with the product on the field as the bottom line, and arguably the best front office mind in baseball running the daily operations.

The word “fans” stems from “fanatics”, however, and even though Theo Epstein indicated it would be a process in his very first official comments as a member of the Cubs front office, fans grew angry over the next 3 seasons as the Cubs roster was being rebuilt from within.

Theo and Chicago Cubs GM Jed Hoyer, thankfully, were less concerned about fanatic reaction and more concerned about following their vision. As Theo Epstein would state:

 “when you make decisions based on fan reaction, it’s not long before you’re just one of the fans.”

Slowly the pieces started falling into place. 
The Cubs would make strategic, one-year signings to flip at the deadline. Some of those playing a major role in bringing back pitcher Jake Arrieta and shortstop Addison Russell, amongst other current roster pieces.

They would deal Andrew Cashner, Ryan Dempster, and Matt Garza during the first 2 seasons, as well as the unpopular move at-the-time of trading Jeff Samardizja in 2014. Slowly, the roster was coming together.

They were also developing players much more efficiently within the system. A near finished product when acquired from San Diego, Anthony Rizzo was provided the means and coaching to maximize his ability. 

After being acquired in the Ryan Dempster deal, Kyle Hendricks was given instruction from one of the best in the business. Derek Johnson was a lesser-publicized, yet extremely savvy signing as Minor League Pitching coordinator.

For some pitchers it would be honing in on command of pitches that were already considered “plus” offerings. For other pitchers it would be developing adequate secondary pitches. Each pitcher would have a personalized plan, however all would have the same objective. Controlling the strike zone. 

Hendricks exemplified how the development of the minor league system had come so far, so quickly under Theo’s watch. A pitcher that would likely had turned into a spot starter/reliever under previous regimes progressed immediately and was named the Cubs Minor League pitcher of the year in 2013. He is now penciled in the Cubs rotation and, even if the Cubs do acquire 2 starters this offseason, Hendricks has a long career as a MLB starting pitcher ahead of him.

Super-prospects have been able to develop and improve as well. Javier Baez, a player that came with the reward of the highest of ceilings and the risk of extremely low floors, was given the time needed to adjust his approach in a way where he can fulfill his FULL potential and not just be a free-swinger at the plate each time.

Going into the 2014 offseason Theo stated that they expected to compete moving forward. The “youth movement” had begun with Jorge Soler, Arismendy Alcantara, Kyle Hendricks, and Javier Baez all making their debuts in the bigs in 2014. Anthony Rizzo and Starlin Castro had both also had bounce-back seasons under new manager Rick Renteria. The stars were aligned.

There was one thing missing, however. That bonafide “we’re serious about winning” type signing. 

The Cubs fans had grown frustrated with the front offices lack of big-name signings. Many had hoped for Pujols or Fielder to be announced in previous offseasons and ignored the fact that the Cubs had been willing to spend big when they felt the player was right, such as they attempted to do with Tanaka. 

The only major signing the Cubs had actually achieved was a complete bust in Edwin Jackson. A move Theo regretted and seemed rushed after Anibal Sanchez had seemingly used the Cubs thought-to-be done deal of 5/75 to maximize his monetary return from the Tigers. It’s fitting he’ll now have to watch from afar as Detroit tries to “reload/rebuild” while the Cubs appear set for the next half decade at least.

With Jon Lester being dealt from the Red Sox to the Oakland A’s at the 2014 trade deadline, he matched everything the front office was looking for. He had World Series experience, he was a left handed pitcher, an ace, had  familiarity with Theo Epstein and Jed Hoyer from their Boston days, and was ineligible to receive a QO, meaning the Cubs would not have to give up their top draft pick to draft him. 

As the 2014 winter meetings kicked off in San Diego, the Cubs had momentum from the recent controversial signing of manager Joe Maddon coming on the heels of a competitive final 2 months of the 2014 MLB season. 

Could Theo seal the deal? Could he bring in that bonafide signing to signal the end of the rebuild?

The week of the winter meetings left Cubs fans across the world refreshing Twitter and browsers at a record pace. Even though Lester would receive an offer of the highest dollar amount being $168 million from the Giants, the decision would come down to the Red Sox and the Cubs.

On December 10th, Jon Lester would sign with the Cubs for 7 years and $155 million, $20 million more than the Red Sox reported final offer. As importantly for Lester was what the Cubs had shown over with their youth development the last couple of seasons, the signing of Joe Maddon signaling the team being serious about contending, and the Cubs appreciation of his involvement in the community. 

Both Lester and team-leader Anthony Rizzo had overcome cancer at different times and both felt passionate about community involvement. 

At his introductory press conference, Lester spoke passionately about coming here to win immediately. Being quoted saying:

“I’m never going to say we’ll be alright, we’ll get them next year”

Completely dismissing the Cubs decades long “there’s always next year” mantra for their century of losing. 

The rest is history. Lester stepped in and did exactly what he was supposed to do in providing the Cubs 5 WARP in his debut season with the club. Though Jake Arrieta would rise up to be the ace of the ball club in his Cy-young 2015 year, the Lester signing had changed the attitude and mentality of the Chicago Cubs. 

The Cubs were no longer the “lovable losers”, no more “wait til next year”. No, the Cubs had won the Lester sweepstakes and had proven they were serious about contending. In case any team had missed the memo,  a trip to the 2015 NLCS would  put the entire league on notice.

It’s ironic, really. Theo Epstein’s end in Boston likely was etched in stone when the ownership pushed Theo to sign Carl Crawford, a high -priced, veteran to a major deal and to trade for Adrian Gonzalez. Yet, what feels like the BEGINNING of the Theo legacy in Chicago likely stems from a high-priced, veteran signing.

Coming to the Cubs, Theo reiterated a long rebuild that would result in a pipeline of talent that would reduce the need for major free agent signings to when the club needed it only to supplement. In 2014 he did exactly that, and the story is only beginning to be written.

Next chapter?  Nashville, TN-Winter Meetings-2015…..