How Will Theo Epstein Lay Out Plans for 2020?

In a few hours, Theo Epstein will sit down and do his annual postmortem press conference at Wrigley Field. It usually takes place a day or two after the Cubs’ season has ended, which means it’s happening a little early this year. For the first time since 2014, the Cubs will not be in the postseason.

You can’t deny that this has been the finest stretch of Cub baseball since the back-to-back championships of 1907 and ’08, neither of which any of us witnessed. The Epstein-era Cubs went to the playoffs four years in a row from 2015-18 and turned the franchise from lovable losers into a team that fans expected to win and be in contention for the World Series every year. That’s a hell of an accomplishment after the previous century.

But now that the playoff streak is over, there are lots of questions to be raised, fingers to be pointed, and, most importantly, changes to be made. Joe Maddon is already out the door, so finding his replacement will be job number one of the off-season. But that’s not all that needs to be done.

When you think about the Cubs this year, here are a couple things to keep in mind.

1. Since the middle of May, they were a sub-.500 team. That’s what they played like, and everybody complained about their lack of consistency and their inability to win close games.

2. The offense needs fixing. Even though they had a positive run differential, most of that was gained in the 23-game span. For over 130 games, the Cubs averaged less than four runs a game. That’s not a championship team, and it’s not even one you want to bring back for another shot.

I imagine Epstein’s going to be pretty coy about who he has in mind for Maddon’s spot as well as the players he has in mind to keep and who he wants to set free. When spring training comes around in late February, we could see at least 2-4 new everyday position players, a couple new bench players, and some new arms.

Four of the five starting pitchers are going to be back except for Cole Hamels, so there will be some competition for one spot. I don’t expect the Cubs to go out and sign another high-priced arm like Gerrit Cole, which means rolling the dice with either Alec Mills, Tyler Chatwood, or Adbert Alzolay. Who knows, maybe Colin Rea will be in that discussion as well.

As for the bullpen, it’s a matter of getting a couple of guys back on track. The Cubs have plenty of relievers stacked up at Triple-A and they’ve been able to go out and find guys on the cheap they can improve. The days of Steve Cishek being trotted out there constantly by Maddon constantly should be over and next year’s bullpen management should be different.

Finally, the postmortem could include some discussion about the Cubs’ MiLB system and draft. With Jason McLeod shifting to a major-league role, Jaron Madison could be next on the chopping/moving block. The Cubs could go outside and bring in someone from the Twins, Rays, or Astros, three systems that are using technology way beyond what the Cubs are currently doing.

I would also expect to see some changes to the structure of the scouting department with McLeod out of the way. This could be an overhaul across the organization, bu the Cubs are not going to go whole hog and strip the MLB team and system of resources this winter. This should be more of a reload and retool rather than a rebuild.

It’ll also be interesting to hear and see just how frustrated Epstein is about this whole mess, a part of which I am sure he will take the blame for. He’s not going to name names, throw anyone under the bus, or tarnish their rep, though we will know by the absence of some individuals just what he thought of their impact, or lack thereof.

In the end, the postmortem will likely leave most of us hanging on a lot of questions about the future. But it should, in the short term at least, point to the new direction for big club and the system as a whole.