4 moves that took the Chicago Cubs from champions to sellers

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Chicago Cubs / Jason Heyward
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Chicago Cubs: Number 1 – The decision to sign Jason Heyward to a mega-deal

How bad is Jason Heyward’s  eight-year,$184 million deal? Really, really, bad.  In 2021 Heyward’s contract carries the 23rd-highest AAV in all of MLB.  All that for a lousy slash of .249/.329/.384 and a .713 OPS.

But the worst part of this deal is the downstream decisions that it created.  First, it meant the Cubs passed on signing Nick Castellanos after 2019.  Is there a Cubs fan who wouldn’t have preferred Castellanos over Heyward at that point (or even still today)?

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Then, pinned up against the 2021 luxury tax threshold, the Cubs were forced to part with Yu Darvish’s $21 million AAV deal at a discount. That’s led to all kinds of issues – most notably a glaring hole atop the rotation and a merry-go-round behind Willson Contreras for the backup catcher role.

Without a doubt, for its longevity, cost, and lack of performance, the Heyward contract is the worst free agent signing in Cubs history.

Chicago Cubs: Number 2 – Theo Epstein broke his own rule about trades

The Cubs were in the hunt for Justin Verlander.  We know that now.  Worse, it seems he wanted to come to the North Side.

Chicago traded for Jose Quintana before Verlander went to Houston but that doesn’t mean the team wasn’t in the hunt beforehand.  Epstein once said that the worst time to make a trade is when you believe you have to.

But he did just that in 2017, sending Dylan Cease and Eloy Jimenez to the South Side for Quintana.  A trade that served no real purpose because the only starting who wasn’t on the 2017 squad from 2016 was the number five guy, Jason Hammel.  Plus the Cubs had Mike Montgomery who was doing fairly well for a number five guy.