Theo’s leaving. Can we go with?
An appreciation of a guy who did it the right way, and is already missed.

We knew it was coming, and soon, but it doesn’t make the news suck any less. Nine years ago Tom Ricketts stunned the world with an uncharacteristic, and fleeting, bout of competence and while looking for a “Theo Epstein type” to take over baseball operations for the Cubs, he somehow ended up with the actual thing.
But Theo has walked away from the final year of his contract with the Cubs. He didn’t have the courtesy to wear a gorilla suit this time when he did it.
Though the reality is that he long ago earned the right to choose when he wanted to go. He took an impossible job, and he made it work.
For the Cubs, his unexpected arrival in 2011 was the first of a series of cosmic dominoes that had to fall in just the right order to put an end to the saddest run in professional sports history.
Epstein arrived to a front office that had nothing. The analytics “department” was a former PR staffer with a calculator and a mechanical pencil, the scouts were all “Hendry guys” looking for the next Josh Vitters, they didn’t have enough office space, and they hadn’t completed screwing over the Hohokams yet to get their new spring training facility built in Arizona.
The task of turning the perennial loser Cubs into a consistent winner would have been daunting enough if Theo just had to worry about getting more good players. But he had to do so much more. They needed a culture change, they needed an identity that went beyond mostly-terrible-occasionally-tragic, and they needed a modern baseball operation.
He came with a plan that involved using the Cubs’ big market advantages to corner the international market, draft college declared prospects in the middle rounds and pay them first round money to buy them out of those commitments, and trade for players in the final year of their deals to get draft pick compensation for them. It was going to allow the Cubs to quickly stock a barren minor league system. It was a great plan, and it was going to work.
And then just months after the Cubs hired Epstein, cheap ass small market Major League owners (and wanna be small market owners like Jerry Reinsdorf) voted to change all of those rules.
So, for the first of many times during his reign with the Cubs, Theo had to change plans.
He brought his old buddy Jed Hoyer over to be the Cubs’ general manager and they convinced Hoyer’s successor with the Padres, Josh Byrnes, to trade them Anthony Rizzo. Ironically, the Padres had Rizzo to trade in the first place because Epstein had traded him to Hoyer’s Padres.
The Cubs struggled on the field under the grumpy leadership of Dale Sveum, but the losses turned into high draft picks. One of them turned into some guy named Kris Bryant. Epstein decided to go less grumpy for 2014 with new manager Rick(y) Renteria, and the Cubs started to show a little on-field spunk.
When the season ended, the Dodgers hired Rays’ GM Andrew Friedman, which had nothing to do with the Cubs, except, it meant that the Rays’ manager had the option to void his contract. After a little subtle tampering and some gas station wine in a Florida RV park, Joe Maddon was the new Cubs’ manager and Jed was off to California to fire Ricky on his doorstep.
During that 2014 season, the struggling Red Sox pulled off a deadline deal that sent Jon Lester to the A’s. Their plan was to bring Lester back as a free agent that offseason, but Lester took his two months in Oakland to get used to the idea that there was life after Boston, and when his old boss gave him the hard sell on the Cubs’ rebuild he bought it.
Lester and Maddon’s arrivals signaled the end of the Cubs rebuild. In three short seasons (that only seemed long while we were trying to watch any of it) the Cubs had transformed themselves on the field and in the front office. It was nothing short of a miracle, only we didn’t quite realize it yet.
The team a year later would stamp themselves as legends, but the 2015 Cubs were just so much damned fun. After a week in the minors to pause his service time clock…I mean, to work on his defense, Bryant arrived in the big leagues and became the rarest of all things…an overhyped prospect who was somehow even better than everybody thought.
Lester struggled for a few weeks and we all freaked out about his inability to throw to first base, and then suddenly the Cubs just figured out how to deal with it. Jake Arrieta turned into Tom Seaver for the entire second half. The Cubs got no-hit for the first time in 50 years (seriously) in late July and then basically stopped ever losing. They roared into the playoffs, which would have been enough but then they dominated the Pirates in the Wild Card Game, and in the most satisfying baseball week of our lives (to that point) they sent the haughty Cardinals packing with a barrage of home runs and strikeouts.
Their sweep in the NLCS to the Mets (who they had gone 7-0 against during the regular season) should have been crushing, but oddly, it wasn’t. For the first time in our lifetimes a Cubs season ended in the playoffs but didn’t feel like the end. We knew bigger things were coming, and the fact we had total confidence in Theo and his plan was a huge reason why.
They thought they stole Jason Heyward from the Cardinals (the fact the Cardinals offered him for more money and he signed with the Cubs without a face to face meeting is still pretty gratifying), from a financial standpoint it hasn’t worked out, but having Heyward has never been the problem, it’s just how much they’re paying him for what they’ve gotten. And, in a shrewd move they added Royals World Series hero Ben Zobrist—even if he did insist on playing his then-wife’s music before at bats.
The weight of 108 years without a World Series title didn’t seem to register with the team, but it was ever present to us, the fans. And as the Cubs tore out to a 25-6 start on their way to a 103 win season we cautiously started to believe that this time, it really was going to happen. They were too good and too oblivious to the past to let it weigh them down. They mounted an incredible ninth inning comeback in San Francisco to escape the first round, and then when the offense finally woke up in the NLCS they took control of the series and cruised to their first National League pennant in 71 years behind a Kyle Hendricks pitching performance for the ages. The Cubs were going to the World Series and they were taking us with.
And then the 108 year history of misery enveloped them like a fog. They fell behind the inferior Indians three gems to one. We were going to have to wait, again.
Or so we thought.
These Cubs Epstein had built were made of sterner stuff. After falling behind 1-0 in game five at Wrigley, Bryant tied the game in the fourth with a homer, and the Cubs added two more, and they hung on with an incredible eight out save by Aroldis Chapman. They never trailed in the World Series again. They cruised to a win in game six and well, you all remember the twists and turns of game seven. After a soul-crushing game-tying homer off of Chapman by Rajai Davis with just five outs to go, the Cubs did it again. They used a rain delay as a reset. They didn’t just have the talent to win it all, they had the guts.
As Zobrist, the guy who got the biggest hit in the history of the franchise in the 10th inning said, “We knew it would be hard. But we didn’t know it would be this hard.”
The Epstein regime was a complete and undeniable success. He came on a mission to do two things, turn them into a modern, consistently successful organization and most importantly to win the whole damned thing, and he had already done both.
Sure, not everything worked. The Cubs have been almost unbelievably crap at drafting and developing pitching since his arrival in 2011, and that lack of home grown pitching required them to pay more for pitchers to fill those voids than they’d planned. Their great young players mostly plateaued, and they didn’t pre-emptively flip any of them before that became apparent to the outside world. The Cubs have only won one playoff series since the World Series.
And yet, the franchise he leaves is 180 degrees from the one he inherited. The Cubs are a consistent winner, they have played in the postseason five of the last six seasons, they are a team players want to play for, they have a scouting and player development infrastructure where there once was none. In short, they are a bona fide successful franchise. We waited a very long time for that.
But that’s not the only reason we’re really going to miss Theo. His ability to build and maintain a team and a franchise is undeniable. He’s a Hall of Fame baseball executive, even now at just 46 years old. But he’s so much more than.
Theo is smart, thoughtful and articulate, and the Cubs had to lean on that a lot during his time with them. The franchise has a lot of people who say and do really dumb and really insensitive things, and Theo’s ability to clearly communicate with an unfailing sense of decency papered over a lot of it. Even he didn’t always handle things the right way. The roll outs of Aroldis Chapman and Daniel Murphy were botched, but then somewhat salvaged by Theo honestly and thoughtfully answering questions and explaining why they did what they did. You believed him because he always made sense. Always. That’s a very rare thing.
When the Ricketts family’s petty disagreements came to light, and their dad’s Islamophobic emails were leaked, and Todd committed a little light property tax fraud, we could be comforted by knowing the baseball side of things was run by a guy who consistently exhibited decency, and actual leadership.
There is no one left to fill that void, to remind Crane that the payroll is going the wrong way because he botched the launch of the team’s TV network and named the spring training facility after a company that makes toilet flappers, or to throw himself in front of the cameras to prevent Tom from delving into petty personal politics.
Jed has his hands full trying to navigate the transition of this current team to whatever comes next now that every good player’s contract ends in 11 months. We make a lot of jokes about Jed. About his height, about him having to be reminded to go to the general manager’s meetings because it was easy for him to forget he was actually the general manager, to every press conference ending with, “Any questions for Jed?” and there never being any.
But he is qualified and prepared for this job. Theo’s last act was to hand the reigns over to a capable successor. Jed won’t be Theo, but the job’s not as stupefyingly big as it was when Theo arrived. That’s not to say there isn’t a lot to do and some huge decisions to be made. Jed will have to find ways to thwart the inevitable penurious impulses of the trust funders who own the team. But we can (and will) worry about all of that some other time.
Today all we should do is thank Theo Nathaniel Epstein for being crazy enough to take on an impossible job and somehow getting it done. We live in a world where we all own a shitload of useless, yet treasured crap with the Cubs World Series Champions logo on it, and our beloved team is no longer the laughingstock of the sports world. We owe that all to him.
Baseball is better…when the Cubs no longer suck.
Thanks, Theo.

In a stunning development, Marquee Sports Network actually covered Epstein’s resignation with an hour long special hosted by Cole Wright, Len Kasper and Bruce Levine and it featured an interview with Theo. I hope they can recoup whatever it cost them to pre-empt whatever German B-league soccer match they were supposed to be showing.
The best part was the chance to play America’s fastest growing game show.
Bruce Levine’s shirt: logo or ketchup stain?


Sure it was our day to record the Bears podcast, but that didn’t stop Mike Pusateri and me from talking about Theo for the last 40 minutes.
