How the Cubs plan to climb out of the 'winner's trap' they now find themselves in

If the buzzword that came out of last year's end-of-season Theo Epstein press conference was "reckoning," the phrase that rises above all others in 2019 is "winner's trap."

Epstein referenced it three separate times Monday afternoon inside the Wrigley Field press conference room, just a few feet away from the Cubs clubhouse that was all cleared out before Oct. 1, with no champagne bottles popped or celebratory toasts.

The Cubs president of baseball operations began his 82-minute season eulogy by thanking fans and accepting responsibility for the absence of postseason baseball this fall. He knows there are high standards set for this team and he - like Joe Maddon and the players - acknowledge this organization fell short of meeting those expectations.

But why did they fall short? Why did Epstein sit in front of the Chicago media (and any fans watching via the numerous live streams) and say many of the same things he said 362 days ago when the 2018 Cubs were stunningly knocked out of the National League playoffs after only one game?

"I think a lot of the issues that we have now started to show themselves towards the end of last year," Epstein said Monday.

While admitting it's disappointing that he's highlighting many of the same problems with this team as he did a year ago, Epstein attempted to explain why, using the idea of the "winner's trap."

"If you want to say we were stubborn with this group, I think that's fair," he said. "We had real belief in this group. To be self-critical and to be honest and accountable, I think there can be a bit of a winner's trap dynamic sometimes where, when you've had great success and won - that group at that time had won more games than anyone else in baseball over those four years - when you look back, you look at the methods and the players and everything that had gone on and you attribute the success to them, rightfully. But it can lead to attributing too many good qualities or placing too much faith in that.

"I think it requires real leadership to move beyond that and that's an area where I need to do a better job as a leader, letting go of the past and focusing on the future. And this is clearly a moment of transition...where we're gonna build something anew."

Epstein said a lot of this came up in conversations with Cubs players throughout the course of the season and while he felt there were some strong efforts made to try to correct the issue from last fall to this one, the problems persisted.

That's why, he felt, there was a major need for change this offseason.

That change began when Epstein announced Sunday morning that Maddon would no longer be the manager of this club, so there will be a new voice and a new field general on the top step of the dugout.

One of the main themes throughout Epstein's press conference was his desire for the franchise to stop looking backwards - especially at 2016 - and instead keep their focus on the future and trying to fix things moving forward.

In other words, he doesn't want anybody to rest on their laurels - and that includes himself and the entire Cubs front office.

For example, why did this Cubs team that was filled with a bunch of World Series winners and battled-tested players need somebody like Nicholas Castellanos to come in and "remind them what hunger looks like"?

Why did they need to get a spark in the middle of a pennant race from a 22-year-old shortstop with only 89 minor-league games to his name (Nico Hoerner)?

"Complacency is a tough word," Epstein said. "If I say there were instances of complacency, it's too easy to paint everyone with a broad brush and I wouldn't do that because I respect our players and their work ethic. I'm getting a lot of this also from our players, they're open with us about things that we as a group can do differently. I think there's a winner's trap of looking backwards - that applies not just to us in the front office, but also to the players.

"There's a lot of looking back at things that have worked in the past. There's a lot of looking back at 2016. There's a lot of reliance on our natural ability and the fact that this is how we do things and we've always come through in the past and a certain mindset that we have here. If you look at the last couple Septembers, you can make a strong argument that that doesn't work anymore. And so we have to try to create a winning culture for now, not what was a winning culture a few years ago.

"We're intent on doing better in that area. All of our players are. They all want to be part of something that's the best culture in baseball. That should be the standard. … We want to have a culture where when a player steps in here midseason, he's not providing energy - there's already energy."

Epstein and some Cubs players - in particular, Kris Bryant Sunday evening - admitted it was difficult to face all these realities last fall, because even though the season ended in a disappointing fashion, this team still won 95 games and they had the best record in the NL through 162 games.

This fall, there is absolutely no way to spin it as anything other than the fact the Cubs fell short.

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How the Cubs plan to climb out of the 'winner's trap' they now find themselves in originally appeared on NBC Sports Chicago