Chicago Cubs: 3 mistakes that led to 2021 dismantle of roster

2. Jason Heyward’s contract

The Chicago Cubs would have been just fine if they never acquired Jason Heyward.

The Chicago Cubs made a terrible mistake when they signed Jason Heyward to an eight-year deal worth 184 million dollars. He was a very good player with the Atlanta Braves and St. Louis Cardinals before coming to the Chicago Cubs but he has not lived up to that contract in any way. He has had a good career with his one All-Star appearance, five Gold Glove Awards, and a World Series championship in 2016 but that contract was just a big mistake by the Cubs.

Sure, he is a good leader and gave a phenomenal speech during the 2016 game seven rain delay. Those types of intangibles are not worth 184 million dollars. Especially when that money forces the team to dismantle their roster way earlier than they wanted to. They had to make big trades involving Rizzo, Darvish, Bryant, and Baez because they simply weren’t paying the roster as a whole all that money.

It will be a while before the Cubs rebuild that roster back to a World Series contender. They are going to want to run their business on a much more cost-efficient level until they see their way clear of this bad contract. They might have been able to have better roster management if they didn’t give Heyward all of this money. This is no disrespect to him as he is a nice man and a good player but he just was never worth that level of money.