Chicago Cubs: Five storylines to watch in the 2020s

Chicago Cubs: How long will Theo Epstein last?

It’s hard to believe, but it’s been eight years since Theo Epstein took over as President of Baseball Operations. In that time, Chicago Cubs fans have seen the lowest of lows (particularly 2012, one of the worst years in team history) and the highest of highs (a championship just four years later).

Epstein will always be remembered as the architect of the team that finally got the job done, just like Joe Maddon will always be the one who led the way on the field. Yet Maddon is gone just three years after it happened, which goes to show that nothing lasts forever in this game (except that championship flag). And it begs the question: How much longer will Epstein be around?

Just like on the north side of Chicago, Epstein was the one who got the job done in Boston, breaking another long championship drought. Yet he too fell out of favor and ended up leaving for the Cubs job. Three years after the championship, Epstein is falling out of favor with Cubs fans, as for the second offseason in a row the team is doing nothing to improve after a disappointing finish to the previous season.

The situation the Cubs’ front office is in right now is largely due to some questionable decisions they’ve made in recent years: the signing of Jason Heyward, who’s been a huge disappointment and still has four years left on his contract; the trade of two top prospects, Eloy Jimenez and Dylan Cease, for a pitcher (Jose Quintana) who’s been essentially a #4 starter; and signing closer Craig Kimbrel to a massive three-year deal when he clearly wasn’t prepared to pitch last year come to mind right away.

Now, the team has no money (or so they say) to bring in anyone new and still have tough decisions on several players, as mentioned above, coming up over the next couple of years. Can Epstein guide the team out of this mess? Or, will ownership look for someone to lead a new direction? There’s no indication right now that ownership is ready to get rid of Epstein, but it will be interesting to see how patient they indeed will be if there’s no improvement on the field in 2020 and beyond.