Bruce Miles: Thanks for the memories, Theo

It's no exaggeration to say that on my final Wrigley Field Sunday as a Cubs beat writer, all Hades was breaking loose around the joint.

The Cubs were in the midst of a nine-game losing streak that would scuttle their 2019 postseason hopes. Just the day before, closer Craig Kimbrel gave up back-to-back homers to Yadier Molina and Paul DeJong to start the ninth inning, turning an 8-7 lead over the St. Louis Cardinals into a crushing 9-8 defeat.

Just as that Sunday, Sept. 22 game was about to begin, my cellphone lit up with a text message.

“Oh, great,” I thought. “Now what?”

Turns out it was a text from Theo Epstein: “Congrats on a great run. Let me know if you ever need anything from us.”

Epstein was in the middle of a whole bunch of stuff that day, from enduring another late-season collapse to coming closer to a conclusion to part ways with manager Joe Maddon, a decision he would announce the following Sunday in St. Louis. So it said a lot to me that he would take a few seconds to wish an old hand well on his way to semiretirement.

The now-former Cubs president concluded his own great run this past week, announcing his resignation after nine eventful seasons in charge of baseball operations on the North Side.

• • •

Covering the Epstein regime on a daily basis from the fall of 2011 until October 2019 was an experience like no other.

In the years leading up to Epstein's hiring, the Cubs front office was somewhat of a mom-and-pop operation, headed up by general manager Jim Hendry, a friendly and gregarious guy who worked for years under the estimable Andy MacPhail, the scion of baseball royalty.

Epstein brought with him a reputation as “the smartest guy in the room,” based on his Ivy League education and a pair of World Series titles with the Boston Red Sox, ending that franchise's championship drought.

While Hendry is earthy, Epstein is erudite. Answers to reporters' questions often were measured in paragraphs, not sentences. But there was a human side as well. During his first few weeks on the job, Epstein and general manager Jed Hoyer hosted the beat writers for an informal lunch at Wrigley Field. Theo went around the table asking about each of us, everything from our family lives to our tastes in music.

When Epstein and Hoyer interviewed managerial candidates that fall, they put each man before the media for a news conference, just to see how they'd respond to reporters' questions. That was something I had never seen before.

• • •

The 2012-'14 seasons were tough to watch, and Wrigley Field was library quiet by the time 9:30 or so rolled around most nights.

For me, the first sign the arrow began pointing upward came on the Fourth of July 2014 when the Cubs again traded veterans for prospects, sending pitchers Jeff Samardzija and Jason Hammel to Oakland for Addison Russell and others. During a conference call the next day, I asked Epstein if this was the last of those kinds of deals he and Hoyer would have to make.

“We talked about that a lot internally as we went through this process, that we certainly hope that this is the last year that we'll be obvious sellers at the trade deadline,” Epstein replied.

You know the rest of the story. The best piece of advice I got from Theo during the 2016 postseason run to the World Series title was to take in each moment and not let it become a blur. I did the best I could with that one.

Epstein's legacy will land him in the Hall of Fame one day, both for his accomplishments in Boston and Chicago, as he broke championship droughts with two of the most iconic sports franchises in the country.

He brought the Cubs front office into the modern era (keeping many of Hendry's scouts, by the way) by introducing advanced analytics to a franchise that had resisted them for so long.

Epstein's trades brought players such as Anthony Rizzo (today's face of the franchise), Jake Arrieta, Kyle Hendricks, Pedro Strop, Miguel Montero and Dexter Fowler.

Although Epstein takes some justifiable heat for his free-agent signings, both in Chicago and Boston, the addition of Jon Lester before the 2015 season may be the best free agent signing in the history of the franchise, and one of the best in Chicago sports history, perhaps behind only Marian Hossa by the Blackhawks.

Free agent Ben Zobrist was MVP of the 2016 World Series and an exemplar of professionalism in a clubhouse filled with young, impressionable players. And although Jason Heyward's offensive numbers may not be what the Cubs hoped they would be when they gave him the huge contract, Heyward has contributed positively to the Cubs in so many ways.

And don't forget the signing of Maddon to manage the team after the 2014 season. Maddon deserved a contract extension just as Epstein and Hoyer got, but that's for another day.

On the down side, the farm system has not produced any pitching talent to speak of, forcing Epstein to buy costly arms. The farm system might not be what it once was as a whole, but that is a bit misleading. On any given day this past season, the Cubs could trot out a starting lineup of such homegrown players as Kris Bryant, Kyle Schwarber, Ian Happ, Albert Almora and Nico Hoerner, along with Javier Baez and Willson Contreras, both obtained by the Hendry regime. It's been a long time since the Cubs were able to do that.

When teams finish high in the standings, they pick lower in the draft, and their farm systems suffer. That's how the system works.

Epstein also drew criticism for obtaining closer Aroldis Chapman in 2016, given Chapman's history of domestic abuse, especially in light of Epstein's talk of wanting “character” players. He faced similar scrutiny for sticking with Russell after Russell's suspension for domestic violence issues.

Bottom line is that every exec in sports has a record of successes and failures. During Epstein's nine years in Chicago, the successes far outweighed the failures, and let's remember that most Cubs fans were totally on board for the “rebuild,” which resulted in those losing early years.

• • •

During Epstein's farewell news conference the other day, he mentioned he'd like to buy Cubs fans a beer if he ran into them in an establishment after the COVID-19 pandemic is over. On the last day of the 2019 season, he mentioned to me that we need to have a glass of wine together.

Thanks for the memories, Theo, and I'm holding you to that offer for the glass of wine.

In the spirit of Ernie Banks, let's make it two.

• Bruce Miles covered the Cubs for The Daily Herald from 1998 to 2019. Follow him on Twitter @BruceMiles2112.