Chicago Cubs: Poor free agent decisions derailed a potential dynasty

Theo Epstein made two critical decisions in the last few weeks of 2015 that altered the fate of the Chicago Cubs franchise. In early November, Dexter Fowler became a free agent after the Cubs declined to re-sign him to a long-term deal.  Six weeks later, the Cubs signed outfielder Jason Heyward to an eight-year, $184 million contract. The first move lead, albeit accidentally, to the Cubs World Series victory. The second helped ensure there would not be another.

Fowler did not remain a non-Cub for long. After his contract negotiations with the Orioles collapsed over the Birds’ bizarre last minute shakedown, Fowler returned to Chicago on a one-year, $8 million deal. He proceeded to have the best year of his career, becoming a key crewmember of the S.S. Cursebreaker.

Heyward, on the other hand, hit the windshield. Google a list of worst MLB contracts and chances are you’ll see J-Hey’s name on it. (Like this one, for example.) Not only has Heyward underperformed even his own modest career numbers (at this writing.708 OPS with the Cubs vs. .750 career), but all that cash thrown at him has been money unavailable to help the team’s other roster spots.

Heyward is the most egregious example of free agent misspending during the Epstein years, but he’s not the only one. The Cubs payroll currently ranks 11th in the majors, and falling. But during their recent heyday, the Cubs ran payrolls that ranged from eighth in MLB all the way up to second. While one can argue Chicago should have shoved in more chips before Bryant and Rizzo turned into pumpkins, it is clear that the money the Cubs did spend didn’t always go to the right places.

Chicago Cubs: A whole lot of money for nothing?

A win above replacement (roughly, every team win beyond the 50th) is generally valued at around $5 million. A player whose cost per WAR is less than that is a bargain.

For example, according to contract data from Baseball Prospectus, in 2016 Bryant and Rizzo were shockingly good values. Together they cost less than $2 million/WAR. These may be among the most efficient Cub player-seasons during the free agency era.

But the Cubs had some inefficient player-seasons too. Defining an inefficient player-season somewhat arbitrarily to mean a player who cost at least $10 million/WAR in a given season and earned at least $10 million that year, the Cubs had 15 inefficient player seasons from 2016 through 2019, the last year for which the BP data is available.

The similarly tanking-and rebuilding Astros had five during the same period. Joe Maddon’s old team, the Rays, had just one (I’m lookin’ at you, Denard Span). Compared to some of the best organizations in the business, the Cubs … weren’t among the best organizations in the business.

Thirteen of the Cubs’ 15 inefficient player seasons came from players signed as free agents. The pain for the most part was spread around. Only Heyward and Jon Lester were multiple offenders; Heyward for all four years and Lester for the last two.

You won’t hear me criticize the Lester signing; as previously noted, his epic 2016 campaign was one of the main pistons in the Cubs’ engine. But increasing salary and declining performance gave that contract’s tail a sting.

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There are other reasons why the Cubs weren’t able to repeat, not least of which is that repeating is probably harder today than ever. While many fans think their own franchise is uniquely freighted with ineptitude, the number of franchises that stand legitimately accused of jaw-dropping incompetence (or simple revenue sharing theft) is pretty small today.  But acknowledging the more competitive environment, the Cubs’ free agent misspending often ended up making their difficult task even harder.