Chicago Cubs: Five reasons the Cubs never became a dynasty

(Photo by Stacy Revere/Getty Images)
(Photo by Stacy Revere/Getty Images) /
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Chicago Cubs
(Photo by Joe Robbins/Getty Images) /

Chicago Cubs: Bad Luck and maybe tough luck here…

First of all, anyone blaming the shortcomings or disappointment of the last few Cubs seasons on ownership not ponying up enough money just hasn’t been paying attention to the Cubs payroll the last six seasons. Sure, the Ricketts could have ponied up 300 or 400 million dollars for a bloated payroll that may not have won any more than what the Cubs did win, but it still wouldn’t have been enough for some fans if they didn’t win.

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The bottom line is that Chicago spent more than enough money to win. The problem is that the team became locked into large and long term deals that hamstrung the team and allowed almost no financial flexibility as the Cubs core got older and more expensive.

The goal was always to acquire pitching and draft hitters, and it mostly worked; yet, when some of those pitchers flamed out or suffered injuries, the money seemed tight. Jason Heyward’s contract was an overpay from the start. Yu Darvish, despite being one of the best pitchers in baseball the past year-and-a-half, struggled mightily due to injury his first year-and-a-half with the club.

Brandon Morrow, newly-signed to a minor league deal by the Dodgers, could never get out of his own way with injuries despite being dominating when healthy. Tyler Chatwood never panned out in the way that Theo Epstein had hoped. Heck, Craig Kimbrel was not good in 2019 or the first few games of 2020, despite turning it around after shaking off the rust in low-leverage spots. And don’t even get me going again on picking up Daniel Descalso immediately after shipping out Tommy La Stella for basically nothing.

By the way, I didn’t even mention anything about some of those trades…