Chicago Cubs History: Ranking the Theo Epstein era’s top 10 moments

Entering a new era under Jed Hoyer is not an easy pill to swallow. Considering the fact the Chicago Cubs have not won a postseason game since 2017 and are now entering “rebuild/retool mode” in what was supposed to be a contention window, there is much disappointment among fans. After 2016 it looked like the Cubs could be the next baseball dynasty. In the end, they were not.

It might be hard to look at this team at the moment and feel sentimental about them. 2016 was supposed to be just the beginning, and now the Cubs are now drawing comparisons to the 1985 Chicago Bears. A young team with so much promise after a championship win, ending up being one-and-done and eventually fading into oblivion. Like the ending of the Ditka-era Bears, this ending has not been particularly pretty. A sad ending to a story that once held so much promise.

With all of that said, this era of Cubs baseball was still the best any living fan had ever seen.

From 2015-2020, Chicago made the postseason five out of six years, won six playoff rounds (WC and series), won 92+ games in four consecutive years (2015-2018), and of course, won that elusive World Series title we had all waited for. If someone told me the Cubs would go on that kind of run back in 2014, I would have been ecstatic. The recent shortcomings are still very upsetting, but remembering the good times is what fans should do as we enter a tough road ahead for the rest of 2021 and beyond.

Here is a top 10 list of moments this core had. As usual, this list is up for conversation and debate.