Jim Hendry to Theo Epstein; It’s not just writing the biggest check

When Theo Epstein came from the Boston Red Sox, he was somewhat of a rock star. The boy wonder that turned around the fortunes of the Red Sox, whose struggles were near as lengthy as the Cubs. Epstein pitched “The Plan”. Along with Jed Hoyer and Jason McLeod, the team would build from within, flip talent where possible; and when the time came, sign the players they needed. But it would require great amounts of patience.

Jun 30, 2014; Boston, MA, USA; Chicago Cubs vice president and general manager Jed Hoyer before a game against the Boston Red Sox at Fenway Park. Mandatory Credit: Bob DeChiara-USA TODAY Sports

It was never going to be easy, and Epstein knew that. Almost 200 losses in two years had people wondering what in the world he was doing. Then, he signed Anthony Rizzo an Starlin Castro-who he called the cornerstones of the plan-to big deals, but at fantastic savings. He essentially was banking on their success, and wagering his job, that signing them early at a better rate was worth the gamble. In 2013 both struggled, and immediately the questions arose..Do they know what they’re doing?

The answer has become a resounding yes.

Rizzo and Castro had bounce back, All-Star campaigns. The rookies that have been the talk since his arrival began making their way to the Cubs; and making statements immediately. Javier Baez and Jorge Soler made huge impacts in their first few games. Kyle Hendricks was brilliant, and Arismendy Alcantara gave the team the initial spark from the rookies.And this wasn’t a case of having a few rookies that, if they bust, there’s nothing else behind them. The Cubs are loaded, thanks to savvy deals and great player development.

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This wave has been great. And Kris Bryant, Kyle Schwarber, and Addison Russell are on the way, just to name a few.

In Epstein’s time in Chicago, it’s become typical for the Cubs to take on pitchers, develop them, and flip them for more talent. Low risk/high reward moves. The Cubs have acquired Arodys Viscaino, and Jake Arrieta through such deals. And pitching coach Chris Bosio continues to take the hand he’s dealt and turn in aces consistently.

Epstein was also able to take Matt Garza, who the Cubs gave up considerable talent for, the best they had in all honesty at the time (Chris Archer), and sent him to Texas for a plethora of talent. Mike Olt, Justin Grimm, and CJ Edwards all came to Chicago, helping level what the Cubs had given up for Garza.

The Ryan Dempster trade brought Kyle Hendricks. Jeff Samardzija and Jason Hammel were dealt to the A’s, bringing Billy McKinney, and the highly touted Russell. He keeps making deals for young players, under team control for several years, and avoiding simply spending big money to get the players to come into Chicago.

It hasn’t been a completely smooth operation. The bloated four-year deal given to Edwin Jackson has hurt the Cubs. Jackson has come close to losing 20 games in back-to-back seasons. Epstein has put Jackson on notice that thing’s have to change, or he’ll be gone.

Jose Veras was signed in the off-season to be the Cubs closer. That quickly soured as Veras couldn’t get ANYBODY out. He was injured, went to the DL for a stint, and was then DFA’d as the team needed to simply realize the mistake, and fix it as best as possible.

In Boston, Epstein built a winner through the draft initially. But when you’re competing with the New York Yankees, who seem to have a limitless account, you catch yourself doing things to “keep up with the Joneses”. some bad contracts left the red Sox in a tough spot, but nothing like Hendry left for Theo in Chicago.

So far it seems Theo has learned his lesson from his time in Boston. A few hiccups, but he’s stayed the course he discussed upon his arrival. The Cubs are very close, if Theo and Co. can add the last few pieces-mainly pitching and veteran leadership-they could contend for the division soon, and on a yearly basis.

Epstein will eventually open the checkbook. But only when the timing is right, and only for the right pieces.