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

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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Nolan Arenado would ‘love’ to play for Cubs, should Rockies move him


Nolan Arenado would ‘love’ to play for Cubs, should Rockies move him

The outcome of Kris Bryant’s service time grievance is in, with an MLB arbitrator ruling in favor of the Cubs. With Bryant losing the grievance, the club can move forward with potential trade talks, now knowing their star third baseman has two more years of club control and therefore more value.

One deal that has reportedly been discussed, at least in earnest, is a one-for-one that would send Bryant to Colorado in exchange for Rockies third baseman Nolan Arenado.

Shortly after breaking the result of Bryant’s grievance, ESPN’s Jeff Passan appeared on NBC Sports Chicago’s David Kaplan’s radio show. Kaplan proposed a trade that would send Bryant, Jason Heyward, Willson Contreras and a prospect to the Rockies for superstar third baseman Nolan Arenado.

According to Passan, the Rockies would hang up the phone if the Cubs offered that package. However, he made one thing certain: Arenado would love to play for the Cubs.

“I don’t think they are at the top of the list right now, even though Nolan Arenado would love to come and play in Chicago,” Passan said of the Cubs. “And I mean he would love it.”

The difficulty of adding Arenado for Bryant straight up is it doesn’t shed any salary, one of the Cubs’ offseason objectives. Arenado is owed $234 through 2026 and $35 million annually through 2024. Bryant will make $18.6 million in 2020.

Kaplan’s proposal would shed salary, though as Passan said, Heyward’s $86 million — or even half of it — would be too much for Colorado. Passan said a more likely scenario is the same deal but including Tyler Chatwood ($13 million salary in 2020) rather than Heyward.

The financial gymnastics of a Bryant-Arenado swap will make a deal difficult to achieve. If Arenado grows increasingly disgruntled with the Rockies, perhaps a trade becomes more likely.

Trading Kris Bryant for Mookie Betts solves literally nothing but it absolutely needs to happen


Trading Kris Bryant for Mookie Betts solves literally nothing but it absolutely needs to happen

Kris Bryant lost his grievance case this morning, which was a big win for the Cubs. Congrats on further alienating one of your best players! Any time you get the chance to ruin your relationship with the only player to ever win the Golden Spikes, Minor League Player of the Year, Rookie of the Year, and MVP in consecutive years, you've just gotta. Take THAT, Scott Boras! 

So what happens next? Given the Cubs' track record this offseason, probably absolutely nothing – but that doesn't make for an interesting article. So here's my idea, and friends, it is dumb: 

The Cubs and the Red Sox are sort of in the same position regarding these two. Both front offices are sufficiently spooked by the idea of market value, which means both players have found themselves fully wrapped up in the trade rumor mill. So why not trade them for one another? (this is rhetorical please stop yelling) Cubs fans deserve something this offseason besides shrewd minor league contracts. 

Here's the Cubs' logic/common sense in general: Mookie Betts is probably the best position player in baseball not named Mike Trout. He's coming off a "down" year in which he posted a 135 wRC+, which was only the 23rd best mark in 2019. What value! He was roughly a 6-win (6.6 fWAR) player in 2019. To put that in perspective, Kyle Schwarber, Nick Castellanos, and Jason Heyward were worth 6.5 wins combined. All of Statcast's fancy numbers say that Betts was basically the same as Heyward in right field last year, too. So Betts, at least last year, was quite literally a combination of Jason Heyward's glove and Kris Bryant's bat (135 wRC+). They're clearly itching to stop paying both of them, a bill that'll end up costing them about $41 million this season; Betts will run the Sox $27 million. Getting the same amount of production for $14 million is quite literally the Ricketts' dream.

There are lots of problems. That move, in a vacuum, would get the Cubs under the luxury tax – but just barely. It'd require the Red Sox, who are ALSO looking to get under the luxury tax (being a big market team is just such a burden), to probably take on an albatross of a contract that prevents them from that. The Sox also have Rafael Devers at third, and just brought Mitch Moreland back to handle first base. Jackie Bradley Jr. and Andrew Benintendi are by no means blocking Bryant from those spots, but the organization specifically brought new GM Chaim Bloom on to avoid these types of deals. 

Both teams would want prospects, too. Neither farm systems are particularly flush with established talent at the moment, but there's actually a lowkey-fun fit there. The Red Sox system's Top-10 is RHP-heavy, which has been the bane of Chicago's existence. There's quietly more upside in the Cubs' minors than they get credit for, so maybe that's a starting point? The Cubs get some righties for The Pitch Lab, and the Sox get some high-ceiling guys that can help better fill out their Top-10. 

To be clear, this won't happen. Bryant-for-Betts doesn't make nearly as much sense as, say, Bryant-for-Arenado might, and trading for Betts would mean shedding even more salary than they already have. But it'd be FUN, and that's something that Cubs baseball could undoubtedly use. I told you guys this was dumb. There's a reason no one liked the Tweet.