Chicago Cubs: Three awful mistakes Theo Epstein made since 2016

Bad Contracts

The Chicago Cubs have some terrible contracts on their roster. They began by giving Jason Heyward a big-money deal with a lot of time on it and that came before winning the 2016 World Series. He takes no blame for it because they did end up winning the World Series. Well, winning it all that year was nice and all, but now they are suffering because he makes all that money despite not hitting very well. Not only does he not really hit well right now, he pretty much hasn’t since arriving in Chicago.

He is an elite defensive player, but you don’t pay right fielders all that money for defense alone. Shortstop or centerfield, maybe, but not right-field. Yes, he gave a speech during the rain delay of game seven and that is about the highlight of this contract. Theo didn’t learn much from that bad contract, however. Tyler Chatwood and Yu Darvish make a lot of money to do a lot less than was expected of them.

Chatwood is a guy that they expected to be at the bottom of their rotation but he couldn’t even command his pitches enough to be the number five guy. He looked like he was going to win that job by the time this spring training ended but that is because nobody else really even challenged him. Darvish has had good games and bad games. When he is good he is really good and can be their ace. They let Jake Arrietta go in his favor so Theo better hope that Yu finishes out his contract on a much higher note.

These deals have made it difficult for the Cubs to improve their team. They don’t have their young big guns on long-term deals and they might lose one or two of them as a result. They need to shed some payroll because of these contracts.