Chicago Cubs: Reasons championship window is quickly closing

Reason #2: Theo Epstein

I was conflicted about including Theo Epstein on this list. After all, Epstein was the mastermind behind the team’s rebuild that culminated in a historic championship for the Cubs. He’s broken two of baseball’s biggest curses and will be a legend forever in Chicago and Boston.

However, it’s tough to ignore some missteps Epstein has made in the aftermath of the 2016 World Series. It’s a criticism Epstein faced after winning two World Series in the Boston Red Sox front office.

Epstein stood before the media after the shockingly disappointing end to the 2018 season and insinuated that big changes were coming. Many fans were hopeful the team would overhaul a bullpen that was underperforming.

Despite some solid free agents being available in the winter of 2019, the Cubs added just one reliever that offseason. After the bullpen issues popped up again in-season, the Cubs desperately signed reliever Craig Kimbrel to a three-year contract.

That deal now seems like a mistake as Kimbrel hasn’t looked right since his struggles with the Red Sox in the 2018 postseason. He got a late start last year by holding out until June, which didn’t help. He blew key saves down the stretch in 2019 but will remain the team’s closer.

There are some concerning reports out there, like Epstein’s failure to acquire pitcher Justin Verlander at the trade deadline in 2017. There are also persistent rumors that he wants to trade superstar third baseman, Kris Bryant.

Epstein may not be the most to blame for the team’s recent failures, but he’s made obvious missteps. I want to see him turn things around, but his hands are somewhat tied by ownership.