Spiegel: Theo Epstein ends a second historic run with elegance

Epstein genuinely cared about those in the Cubs organization during his tenure, and it showed.

(670 The Score) While interviewing Theo Epstein during the 2015 season, I mentioned to him a favorite story from his first curse-breaking title in 2004.

There’s a graveyard in Boston, not far from downtown, off Tremont St. near the Common. The night the Red Sox won, a man couldn’t help himself and hopped the fence to share a moment with his deceased father. A policeman’s flashlight stopped him cold. As he apologized to the cop, he prepared to be arrested -- or at least sent back outside the gates.

“Are you kidding?’ asked the cop. “Look around you.”

There were dozens of people already there, doing the same thing with hats and tears.

Epstein knew that graveyard and treasured being the man who helped those fans have that satisfaction in leading the Red Sox to a World Series title.  He brought that same dream to Chicago, and it genuinely meant something to him as he led the Cubs' baseball operation.

Imagine now embarking in late 2011 with three years of “not prioritizing winning on the big league level,” all building toward a hopeful shot at the title, knowing all the time the emotional, generational weight that fans brought to the endeavor.

Then, imagine actually getting it done. You’d go on a bender too.

Epstein brought a holistic approach to the Cubs organization that it desperately needed. There was so much that needed to be done. A real analytics department needed to be created. Facilities at every level needed to be modernized, with an eye toward development practices becoming standardized and taught with consistency.

With Epstein now on his way out after nine seasons in charge, the holistic approach was obvious once more. New top baseball executive Jed Hoyer is armed with revamped scouting and development departments, a product of last offseason’s intensive focus. Chairman Tom Ricketts was in lockstep with Epstein for this peaceful transfer of power, removing as much drama and discomfort as possible.

We all learned to be smarter baseball fans during the Cubs' build. Even if you disagreed with “The Plan,” its sensibility was undeniable, and Epstoyer’s commitment to eventually delivering fans a full meal instead of the occasional cookie was unwavering. Their patience taught us patience.

And Epstein's Cubs got it done, winning a championship in the fifth season of a five-year plan. It was perfect. Probably too perfect.

Immediately, Epstein had to enter the “maintenance” phase of trying to continue the winning ways. This has never been his favorite part. Free-agent contracts brought mixed success. Yu Darvish’s broken 2018 was immensely damaging to multiple years in the window, as his failures led to the acquisition of Cole Hamels and the necessity to pick up that costly contract option.

The failure of the Cubs' offense in big moments down the stretch and in the playoffs over the last three years was painful. Every offseason, Epstein would suggest the need for big change, then shy away from breaking up the beloved core, believing it could improve and perform.

This year, this winter, it must be done. At least two of the five Cubs position players set to be free agents after 2021 won't see Opening Day. Having drafted and/or developed these players and built lasting friendships with them, would you want to be the one who sends them away? When you yourself won't be here to deal with the ramifications in the clubhouse and on the field?

Me neither.  Must be nice to have a Jed to do dirty work as the next phase beckons. And the financial freedom to refuse one final year of salary.

Two iconic franchises both evolved mightily on the business side as Epstein led them to winning and beyond. That wasn't happenstance. Both could've moved out of their landmark shrines, to the suburbs or another city entirely, but instead found ways to stay and grow. They both ended parasitic relationships with neighbors, buying property around the parks that lead to income. They both made space for luxury suites and advertising that transformed the economic model. Epstein was the dream partner for such progress.

This is because all the while, he genuinely cared about the people involved, completely honored the integrity of the winning goals and spoke candidly about the challenges that came his way. To be a part of the corporatization of tradition, while not letting the machine dilute the compassion, is remarkable.

In his final visit with the media, Epstein spoke to some of the game’s larger issues. In fact, he took some responsibility for the quality of the sport on the field, overall. He’s spoken about this stuff privately for years. The strikeout rate is out of control. Strategy within the game has developed with a near-uniform methodology that's undoubtedly more efficient but isn't the most aesthetically pleasing. This is why we should all be open to rule change conversations. We must accept, as he has, that to love the game is to be open to its advancement and survival.

Theo for commissioner?  Too much owner backside to smooch.  But he’ll make his opinions known.

When he, Hoyer and Jason McLeod arrived, they were young, handsome, exciting and -- in terms of winning -- exotic. Score colleague David Schuster said their opening press conference reminded him of The Beatles.

Epstein's letter to “Cubs Friends” on Tuesday (a must read) and the accompanying press conference showcasing his trademark eloquence was the “Let It Be” concert on the Apple rooftop in London.

One beautiful, final fleeting glimpse of greatness.​

Matt Spiegel hosts Hit & Run and Inside the Clubhouse on 670 The Score. Follow him on Twitter @MattSpiegel670. For more from and about Spiegel visit​​​