Reflections on the long, successful Cubs tenure of Theo Epstein

No matter what you think of Theo Epstein’s nine years as Cubs President of Baseball Operations from October 2011 through the end of this week, this is the most important thing to remember:

Photo by Patrick Gorski/Icon Sportswire via Getty Images

That’s really all that matters. Tom Ricketts said, on the day the Ricketts family took control of the Cubs October 30, 2009, that one of his goals was to win the World Series. Two years later, Theo was hired to create a baseball operations department that did exactly that.

That’s something that more than a century’s worth of previous Cubs ownerships and executives could not accomplish.

For that, and for doing the same drought-busting in Boston, Theo Epstein’s place in baseball’s Hall of Fame is assured, some years down the road.

For that, every Cubs fan, myself included, will be eternally grateful. During his final news conference as Cubs President of Baseball Operations Tuesday afternoon, Theo offered to buy any Cubs fan who runs into him a beer, once the pandemic is over and bars can safely re-open. The thanks I have to offer him and his baseball ops team for making my dream, and every Cubs fan’s dream, come true, will last the rest of my life.

The legacy Theo leaves is a bit more complicated, though, so let’s take a look at what he accomplished in those nine years he ran the ballclub and where things stand as he departs.

When he took over, the baseball ops side was in shambles. There was little talent in the farm system — though, to give Jim Hendry credit, Javier Baez and Willson Contreras were beginning their careers and turned out to be stars still producing for the team — and that side of the ballclub wasn’t up to speed on analytics and was short on scouting staff. Theo bolstered both those areas; sadly, they have been somewhat decimated by the pandemic. Hopefully, Jed Hoyer will be able to hire back some of those let go when baseball returns to normal.

When Theo was first hired he spoke of “parallel tracks,” which I took to mean he’d try to put together a competitive team on the field while still rebuilding the system. In hindsight, this wasn’t the right thing to do and I was wrong when I complained about the awful losing seasons of 2012-14. Theo was ahead of the curve in “tanking,” as it came to be known, and without those losing seasons the Cubs don’t have Kris Bryant, Kyle Schwarber and Ian Happ, so that worked out all right.

He made shrewd trades in the early years of trying to rebuild things, acquiring key parts who would become important pieces of the World Series team: Anthony Rizzo, Jake Arrieta, Pedro Strop, Dexter Fowler, Kyle Hendricks, Carl Edwards Jr., Justin Grimm, Miguel Montero and Tommy La Stella, among others. Theo pounced on signing Joe Maddon to manage the team right after Maddon opted out of his Rays contract, even though Rick Renteria was still signed to manage the club. It was a tough thing to fire Renteria when he hadn’t done a bad job, but Maddon was the right choice for that particular group of players at that particular time in history. Further, I don’t think Jon Lester signs what’s probably the best free-agent contract in Cubs history if not for Maddon’s presence. That indicated to Lester, I think, that Theo and the Cubs wanted to “win now.”

Some of his other deals and signings didn’t work out. He spent $52 million over four years to sign Edwin Jackson, and Theo admitted later that had been a mistake. He traded DJ LeMahieu for Ian Stewart, and though it’s likely that no one could have predicted the stardom for LeMahieu that he now enjoys, Stewart was a bust on the field and was released after he dissed the team on Twitter. He traded Jorge Soler for one year’s worth of Wade Davis, and though Davis had a good year for the Cubs, Soler became a star in Kansas City, finally healthy. He made controversial trades for Aroldis Chapman and Daniel Murphy. Personally, I believe the Cubs don’t win the World Series without Chapman; they could have done without Murphy and I think Theo hung on to the disgraced Addison Russell one year too long.

The signing of Yu Darvish could pay dividends for the Cubs for the next three years and Jason Heyward, while perhaps not worth all the money he received when signing before 2016, has still produced solid value for the team on and off the field.

But those sorts of things happen to every baseball executive. Not one of them hits on 100 percent of their transactions. The biggest failure, though, in bolstering what had been a bottom-third organization, was the complete lack of drafting or signing and then developing pitching talent. Until Adbert Alzolay came along, the only pitcher who the Cubs had developed under Theo’s regime who had pitched in the big leagues was Pierce Johnson. Alzolay might still turn into something good, as might Brailyn Marquez, but the failure to have proper pitching development turned the Cubs into a “let’s see who’s on the relief scrap heap” team as opposed to many other teams who seem to trot out a constant stream of relievers who can throw 95-plus. This is something that Jed Hoyer and his team, whoever’s on it, will have to address going forward.

For his part, Theo does seem to understand himself quite well:

“If you look at my track record in Boston and then here, in the first six years or so, we did some pretty epic things and then the last couple years weren’t as impressive,” Epstein said. “Maybe what that tells me is, I’m great at and really enjoy building and transformation and triumphing. Maybe I’m not as good and not as motivated by maintenance, so to speak.”

The Cubs under Epstein did draft and sign good hitting prospects. I mentioned Bryant, Schwarber and Happ, and of course there’s also Gleyber Torres and Eloy Jimenez, who departed in trades. That’s one use of prospects, to help you win by trade, and as noted above, I believe that did happen in 2016 with the Torres trade and had Jose Quintana helped the Cubs win another World Series, the Jimenez deal would have been seen as useful as well. Unfortunately, that didn’t happen, but Cubs scouts did identify and draft hitting talent under Theo’s leadership, and I hope that continues.

Theo Epstein’s leadership brought Cubs baseball operations out of the Dark Ages. Before 2011, they were operating in a 1980s mindset, and that 1980s mentality had replaced a regime, under the Wrigleys, that had spent four decades working like it was still the 1930s or 1940s. For the modernization of baseball ops under Theo, we owe him many thanks. The team’s never going back to those old ways.

Theo promised us a team that would perennially contend and get as many chances at winning a World Series as possible, and he absolutely did that. Yes, the team won just once under his leadership. But they made the postseason five of the last six years, and if they’d won just one more regular-season game in 2018, maybe that year ends differently, too. Winning the World Series is hard. There’s a reason why no team has repeated as champion in 20 years.

One World Series? I had begun to despair that I wouldn’t see that in my lifetime. Is it enough? I’ve asked that question here before, and while of course I’d like to see another, or three, in some ways one is enough. The flag shown at the beginning of this post flies forever. The trophy belongs to the Cubs forever. I bought a replica World Series ring and I’ll have that forever. This is the mindset that Theo created, as he remembered Game 7:

I asked Mike Bojanowski what he thought about Theo’s departure and here’s what he told me:

There is a single, overwhelming aspect to the history of the Cubs, despite all their past glories. It can be summed up in one number: 108. Every fan of a team expects a championship at some point as a reward for their loyalty and investment of emotion. And every fan knows that, unless he is lucky enough to latch onto a team favored by time, circumstance, or history (e.g. Yankees), that such titles are usually a generational occurrence. I remember, as a little kid learning the history of my chosen team, for the first time looking at the list of World Series champions to find out when the Cubs had last won. And finding it, saying to my younger self: “Are you KIDDING me?!” And that was back THEN.

What the Cubs and their fandom endured is so inexplicable, so unlikely, so marred by almost tragic chance, that one could be forgiven for entertaining curses as the underlying cause. Undoubtedly, as it continued for decades on end, it became a palpable, if not crushing, burden on every Cubs team and front office.

Epstein destroyed that mindset from the front office, Maddon from the dugout. That legacy is unassailable. They have my imperishable gratitude as a fan of the Cubs and of the game. Given the prehistory, this six-year run of success is the greatest golden age in the long existence of this franchise.

If the current game tells us anything, it is that the athletic moment is fleeting. It happened once to this team, and that may need to be enough, nor is it denigrating to say so. It’s enough for me, and that little kid waited over fifty years. It may be, incredibly, a disappointment for some, but I can accept that with, at long last, a sage smile.

Thanks, Theo, for the trophy and for the memories, and best of luck wherever you go next. And I do think I’ll take you up on that beer.