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3 Theo Epstein mistakes that ruined Cubs’ chance at a dynasty

By Vincent Parise

CHICAGO, ILLINOIS - OCTOBER 28: Theo Epstein, president of baseball operations of the Chicago Cubs, looks on as David Ross, new manager of the Cubs talks to the media during a press conference at Wrigley Field on October 28, 2019 in Chicago, Illinois. (Photo by David Banks/Getty Images)
CHICAGO, ILLINOIS - OCTOBER 28: Theo Epstein, president of baseball operations of the Chicago Cubs, looks on as David Ross, new manager of the Cubs talks to the media during a press conference at Wrigley Field on October 28, 2019 in Chicago, Illinois. (Photo by David Banks/Getty Images) /
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The Chicago Cubs are very bad. They have a better chance at last place in the National League Central Division than they do first place and it isn’t really close. There are a lot of people that deserve blame but one guy seems to get a pass all the time.

Theo Epstein is a legendary future Hall of Fame baseball executive. He helped both the Boston Red Sox and Chicago Cubs end close to century-long World Series droughts. He deserves a lot of credit for that as he is one of the best to ever do it.

However, he was not perfect. There were a lot of mistakes that were made that kept them from reaching another World Series and potentially winning one. After the surprise run in 2015 ended, it looked like they had multiple World Series coming their way.

Unfortunately for them, it didn’t work out like that. There were some mistakes made along the way that kept them from having a dynasty. These are the three biggest ones made by Theo Epstein during his tenure:

1. Signing Jason Heyward

The Chicago Cubs should have never given Jason Heyward the contract they did.

Jason Heyward was a very nice player with the Atlanta Braves and St. Louis Cardinals before getting his contract with the Cubs. However, it was obvious from the beginning that the contract they gave him was going to be hard to navigate around.

To be honest, it isn’t the fact that it is worth 184 million dollars that makes it the worst contract. It is the fact that it was for eight years and the Cubs had to deal with it as he started to really decline.

He was always a mediocre hitter with an elite glove but now that he is pretty bad at hitting, it looks even worse. He gave a really nice rain-delay speech but you don’t pay that much money for that long for a speech. Epstein would probably take this one back if he could.

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