MESA, Ariz. — If anyone lacks a clue about how to guide a team to back-to-back World Series titles, it’s hard to top Theo Epstein.

Epstein was general manager of the Boston Red Sox when they won World Series in 2004 and 2007. After becoming president of baseball operations for the Chicago Cubs, they won the World Series in 2016.

“I’m the wrong person to ask about how to repeat, but I am really experienced about answering questions about why it’s so hard to repeat,” Epstein said before the Cubs took on the Red Sox in the final spring training game for both teams.

“Because I’m 0-for-3.”

Epstein has tried (his 2005 Red Sox were swept in the Division Series), tried (2008 Red Sox: lost the 7th game of the ALCS) and tried again (2017 Cubs: lost the NLCS in five games).

Not that he thinks the 2019 Red Sox would have much of a chance against the Cubs in case of a World Series matchup this October, but Epstein happens to see encouraging signs from his former team.

“Watching and reading the clips from Red Sox camp and talking to a couple of my buddies over there, this team, it feels like they’re a really together group and you don’t get a sense at all that they’re going to be victims of a hangover,” said Epstein.

And that “hangover” effect is very real when it sets into the mindset of a reigning champion, said Epstein.

“Obviously ’16 to ’17 is freshest in my mind but there can be this sense that if you’re not careful, that when you report to spring training after winning the World Series, it feels like you’ve just climbed Mt. Everest, and what feels like just a few weeks later, even though it’s a few months later, you’re asked to do it again,” said Epstein. “How do you take that first step? You just got to the mountain top. I’ve had players admit this to me, that it can be disorienting. There’s a risk of not being fully bought in to the daily routine and the daily grind in the face of having just been so high on the mountain and then having to take the first step of the journey again.”

In addition to that challenge of a motivational re-boot, there is also the task of overcoming a sense of complacency that can settle in.

“There can be this risk of – and I’m not saying this applies at all to the Red Sox, I don’t know their situation – there’s always a risk of a sense of entitlement that creeps in,” said Epstein. “Players and front-office members, everyone goes home for the winter and after you’re all together for the whole postseason, you go home and no matter how selfless or benevolent or altruistic you are, it always reaches a point where you look in the mirror and say ‘Well, I was a pretty big part of that – what about me?’ Sometimes your agent is telling you how much you contributed and how much that’s worth – it can risk that great team connection that brings you the success in the first place, and that can be jeopardized with all the aftermath that comes with winning a World Series.”

Three years later, Epstein is all in on finding the right methods to re-motivate his still young and still elite Cubs team into repeating its 2016 magic. He is also still highly attuned to what goes on in Red Sox land and as he said, he keeps in touch with former associates still with the organization. Yes, he does retain plenty of pride about that 2011 draft class (Mookie Betts, Jackie Bradley Jr., Matt Barnes, Blake Swihart, Travis Shaw) and that he experienced, to a certain degree, joy from their joy when they won it all in 2013 and 2018.

That lack of letdown that Epstein is picking up on in this 2019 Red Sox team does not seem to surprise him, particularly when it comes to Alex Cora. He knows Cora well, having both traded for him (2005) and signed him as a free agent (2006). And what he saw from Cora last season and particularly in October sparked a significant amount of respect and admiration that bordered on awe from Epstein.

“You never want to be watching the postseason, you want to be in it, but the best part of watching the postseason last year was seeing how brilliant Alex was in every phase,” said Epstein. “Strategically, he pushed every right button and was incredibly creative how he integrated the starters into their bullpen mix, and then also his personality helped define the very nature of that club. You could see them becoming extremely assertive, extremely confident, just like he is. You could sense it from the way they were playing. That was as fine a job as a rookie manager has probably done in the history of baseball, it was just incredible. It was fun to watch.”
Epstein said that from his couch vista he was not employing any kind of “deep psychology” in analyzing Cora’s leadership. It was right there in his face.

“I know him,” said Epstein. “Everyone who knows him knows how confident he is, how assertive and aggressive, how engaged and into the game. There can be a risk sometimes in the postseason of over-managing and he never entered that territory. Everything he did was two steps ahead. It worked out. He knew his team better than anybody else, he knew what was possible. They kept their (pitching) plan secret and that was a big strategic advantage for them. You could tell the players believed in every little thing he was doing. I think it created a real competitive advantage of ‘belief.’ They were sort of dictating each game. They had a plan but it was adjustable and they were able to dictate some key moments in each game.”

That said, Epstein will do everything in his powers to have the Cubs spoil the Red Sox’ repeat bid.

But if they can’t, and the Red Sox do repeat, Epstein does not sound as if he will be that shocked. At least he’ll stop being asked about repeating as world champions. Dave Dombrowski can take over instead.