The Chicago Cubs were looking very good in 2016 to be a great team for a long time. Since then, some terrible decisions have them in a tough spot.
The Chicago Cubs have one of the best President of Baseball Operations in the history of sports. Theo Epstein is best known for ending two century-long World Series droughts by two of Major League Baseball’s most prominent franchises in the Boston Red Sox and Chicago Cubs. He deserves credit as one of the greatest of all time for those feats alone.
He has made it where both teams to this day are in very good spots financially and beyond. With that said, Theo Epstein has made some major mistakes with the Cubs over the last few seasons. For some reason, the media wears their rose-colored glasses when it comes to Theo but not here. He has made some mistakes that have turned the Cubs from a perennial contender to a team that very well could miss the playoffs for the second year in a row.
They still have their four most important position players well in their prime yet the team around them is average at best. They were in a position to make it to the playoffs late in 2019 but fell off at the trade deadline. He deserves credit for his triumphs and he gets it but for some reason, it is hard for people to talk about the things he has done wrong. The Cubs should not be in the position that they are and Theo deserves some blame for it.
He is a very smart man and might get this team out of it if the owners let him, but he hasn’t been perfect since winning the World Series in 2016. Since then, these three mistakes have been the most notable: