Theo Epstein Says Cubs Will Try to Escape ‘Winner’s Trap’ This Offseason

So how would Theo Epstein top last year’s 71 minutes of napalming the organization with calls for more urgency from a broken offense? By going about 10-15 minutes longer and saying even less (watch the full video here). While there were some interesting nuggets in there, a large majority of the conversation touched on problems that have been apparent for at least a year or two.

If we were to distill the whole thing down to a single catchphrase and concept, it’d be that the Cubs need to get out of what Epstein called the “winner’s trap.” They achieved success in 2015 and ’16 on the backs of young hitters and veteran pitchers, trading off a wealth of young assets to fuel that dynamic. But what worked in the past won’t always work in the future, a reality the Cubs acknowledged when they let Joe Maddon become a free agent.

Epstein bore all the blame for the Cubs’ issues while speaking glowingly of Maddon, not to mention ownership’s willingness to spend, which is as it should be. Of course, that blame was a little easier to hoist when so much fault had already been strapped to Cousin Eddie to be hauled away to parts as yet unknown.

The Cubs have fallen behind, Epstein said, and their goal this offseason is to play catch-up in terms of player development and culture. Once the archetype of holistic organizational culture-building, the Cubs became a team that needed constant injections of energy via trade and promotion as the season wore on. Once a team that made other players want to be better, complacency has taken hold and must be shaken off.

That is where a managerial change is really expected to have an impact, though such a move will only be effective if the players buy in. As such, there were be personnel changes on the roster as well as in the front office and coaching staff. The Cubs will create roles for directors of hitting and pitching to ensure greater developmental continuity and prevent the kind of stagnation they’ve seen when it comes to success with pitching prospects and lower-round draft picks.

Though they’ve not deviated much from the idea of drafting more polished college hitters early, the Cubs may be shifting away from the notion that players should reach MLB as nearly finished products. It’s a young man’s game and Epstein admitted the need for development to continue at the highest level, which could mean keeping Nico Hoerner in Chicago to open the 2020 season.

The organization has very obviously struggled to develop pitchers during Epstein’s tenure, a failure that was at least partially to blame for Jason McLeod’s transition out of minor-league oversight. Early returns from their Pitch Lab have been good, elevating players like Rowan Wick, Brad Wieck, and Kyle Ryan, but that’s the kind of stuff other successful teams have been doing for years.

The Cubs’ efforts have gone wanting when it comes to things like tunneling, sequencing, and velocity increases, areas in which the Astros and other teams have excelled. That’s why the pitching never caught up to balance out the early influx of hitters, forcing the Cubs to keep spending big on arms and eroding their margin for error all the while.

The residual effects of those failures could mean trading away some of their core players, something Epstein hinted was a possibility if long-term deals can’t be reached. This really isn’t anything different from what he’s said in the past, repeating familiar tropes like not having untouchable players and being willing to listen on anyone. Naturally, there could come a point at which a trade proposal makes sense because the Cubs need to get something back from a player who might otherwise bolt for free agency.

At the same time, the front office isn’t trying to rebuild the whole thing over a two-year period and trading away players like Kris Bryant or Javy Báez would be indicative of wholesale change. Reconfiguring the periphery is much more likely, with second base and center field standing as obvious positions for improvement. Hoerner fills one of those spots, maybe both, but it sure seems as though Albert Almora Jr. is no longer being considered as a solution.

In the end, Epstein himself acknowledged that words weren’t going to get it done. He surely understood that last season as well, but hammering concepts like urgency and edge ended up meaning nothing where there were no tangible actions behind them. That is going to change moving forward, or at least it had better if the Cubs expect to do better than a third-place finish with a team that appeared to be going through the motions far too often.

How things will look different next year is anyone’s guess at this point, with a new manager as the only certain change. All the signs at this point are that David Ross is the top choice, but Epstein would only confirm that the cult hero was on a “broad list of candidates.” Ross was, however, the only candidate mentioned by name, primarily because he’d already discussed the possibility on ESPN. Current bench coach Mark Loretta is thought to be on the list as well, though Epstein declined to confirm that with staff meetings scheduled for Tuesday.

All he would cop to is that there was one potential candidate from among the current coaching staff, which seems very light given how many of those men were hand picked by the front office. Even with the calls to change culture for the better, you have to think several of the coaches will stick around under the new skipper.

No longer working with the luxury of time and low expectations, Epstein and the rest of his revamped front office will now have to put actions behind these words. They can’t miss on trades or signings and they need to get someone in that dugout who will set the tone for a reinvigorated culture. As odd as it may sound, I believe we’ll know pretty quickly just how successful this offseason overhaul is going to be.

It’ll take more than a week, but maybe not much more than a month for the Cubs to show us who they are with the way they play. And if that play looks like what we saw most of this season, that whole “season of reckoning” may really come to pass.

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