Theo Epstein has conquered every challenge thrown his way since coming to Chicago.

He has torn down and rebuilt the Chicago Cubs organization from top-to-bottom, implementing a system of vertical integration that baseball’s best franchises such as the Yankees, Dodgers and Cardinals have been using for decades to build and sustain winners. He has created a development machine that churns out young, flexible talent worthy, willing and able to play multiple positions at a moment’s notice.

And most importantly, he built a World Series champion.

Yet, Epstein finds himself with his eyes on a new mountain to climb. In an exclusive with Jon Greenberg of The Athletic, Epstein underlines what’s next for the Chicago Cubs.

When you finally win it all, new challenges arise.

“We have to avoid organizational arrogance setting in. We have to avoid entitlement. We have to avoid, and not to just players but front office types, looking more at themselves than the group,” Epstein told Greenberg. “We have to remind each other the best part of the 2016 experience was being part of something bigger than yourself. That’s going to take some nurturing going forward.”

There is a flurry of many other things going on in this piece, so I encourage you to read it over at The Athletic to get the full scope.

The 2016 Cubs – 45 players plus coaches, front office, staff and others – came together with the goal of bringing down the 108-year elephant in the room. Even with the accomplishment of that goal, Epstein realizes the next challenge isn’t just winning another World Series – it’s doing so while avoiding the kind of complacency that naturally comes after a great success. The 2016 World Series champions had the perfect mix of talent and selflessness.

And while the 2017 team is made up of a lot of those pieces, it won’t be the same team we saw in 2016. Yet, the goal is to repeat what the 2016 team did. No easy feat.

No team has repeated as World Series champion since the Yankees’ three-peat from 1998-2000. And it’s rare to see teams win back-to-back National League pennants – only the 1995-96 Braves and 2008-09 Phillies have done it in the last 22 years.

It’s interesting to see Epstein with this kind of big picture vision in January, weeks before pitchers and catchers report to Mesa. Once again, the Cubs aren’t avoiding the elephant in the room. Instead they are taking it head-on.

Epstein’s exclusive with The Athletic wasn’t the only recent deep dive into the mind of the Cubs’ top baseball executive. David Axelrod, a Cubs fan who is best known for being the Chief Strategist for Barack Obama’s presidential campaigns, sat down with Epstein for a lengthy chat on his podcast – The Axe Files.

Episode 113 sprays to all fields, with Epstein discussing everything from his childhood dream of playing shortstop for the Red Sox, how The Cubs Way manual came together during a four-day stay in a Mesa hotel, the similarities between sports, politics, and the role of media in those two arenas, why Branch Rickey will forever be The G.O.A.T. of baseball executives, how he bungled the GM search in Boston and more.

You can check out the entire podcast here – and believe me, you’ll want to dive into this one. But before you do that, some highlights:

  • Want to work in The Show? Epstein provides some quality advice on how to make it through sheer work based on his experience with the Padres. “Whoever your boss is or bosses are – 20 percent of their job they just don’t like. So if you can ask them or figure out what that 20 percent is and figure out a way to do it for them, you’ll make them really happy and improve their quality of life and work experience. And also gain invaluable experience for yourself. If you do a good job with it they’ll start to give you more and more responsibility.” [Brett: Wow. I didn’t know how true this was until reading it right now. Gonna need to call a staff meeting …. ]
  • Things were going so well for Epstein in San Diego, he was reluctant to leave before departing for his dream job with the Boston Red Sox. “I turned down an assistant GM job elsewhere just to stay with the Padres at a lesser position because we had such a tight-knit group and it was such a nice life out there. But it felt like time. The Red Sox was my ultimate dream. They were the ultimate ivory tower franchise.”
  • Epstein detailed how he has grown to appreciate and value a player’s makeup during the evaluation process, which is something he hasn’t always believed in. “When I first started working in baseball, I felt that talent always would triumph in the end. With every year I’ve spent in baseball, I’ve gained an increased appreciation for the importance of the chemistry of the group, the importance of filling your clubhouse with as many good teammates as you possibly can, the importance of the connections, relationships, conversations …. It’s not always the most talented team, but the best group with the most talent that wins.
  • With his contract renewed for another five years, does Epstein already have eyes for what he wants to do after his deal is up? “I think we have a lot more work to do with the Cubs. We have the opportunity to win a lot and I think our fans deserve that because they’ve been through a lot,” Epstein said. “We’d love to win a lot over these next five years. We have our best players under control through 2021 – basically the whole nucleus. We’d love to go out and become one of those teams like the Yankees or Braves that is synonymous with October baseball and plays in – and hopefully wins – multiple World Series. I haven’t thought much beyond that.”
  • As for moving up into a potential ownership role one day, Epstein sounded intrigued when he replied “sure” to Axelrod’s question, adding: “I think you can do things as an owner that you can’t necessarily do as an employee in helping the team really get involved in the community and doing some great work using baseball as a vehicle to do some important work for society.

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