Chicago Cubs: Theo Epstein learning from Dave Dombrowski’s failures

For all intents and purposes, there is a bit of a new tone with which Chicago Cubs brass are approaching this offseason – a breath of fresh air for the club.

Past winters have been marked with a sense of urgency in terms of putting a winning product on the field at nearly any and all costs. Recently, however, an exorbitant payroll and consistent disappointments have led to more timidity from the Chicago Cubs front office.

Now the theme, according to The Athletic is: “extending the window of contention” (subscription required). Instead of retaining pieces that, back in 2016, were vital to Chicago’s future, there is a very real chance that members of the young core could be out the door this winter.

We’ve already heard rumors involving two-time All-Star catcher Willson Contreras and former National League MVP Kris Bryant. I mean, we’ve even heard very loose discussions on social media about the team dumping payroll in a Craig Kimbrel deal (although those, to this point, are unsubstantiated).

Is it possible that ownership is wary of recent internal failures of teams such as the Boston Red Sox and former president Dave Dombrowski?

Chicago Cubs: Spending has put the Red Sox in a tough spot

Initially, Dombrowski’s ridiculous spending habits did lead to somewhere.

“Dealin’ Dave” practically threw money at J.D. Martinez and the slugger, in turn, nearly won the Triple Crown in 2018. David Price (who signed a record-breaking deal with Boston in 2015) was arguably their best pitcher in October as Boston won the World Series.

But in 2019, they were exposed for a lack of quality in the starting rotation as well as the absence of a late-game stopper in the bullpen.

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Sure, Dombrowski locked up Chris Sale and Xander Bogaerts with huge extensions. But he also signed the oft-injured Nathan Eovaldi to a big deal on top of the payroll already consumed by aging veterans like Price and Rick Porcello.

Consequently, the rotation regressed significantly and the Red Sox had to rely on internal replacements in the bullpen. The relief corps rebounded in the second half, but the starters never bounced back in the wake of injuries to Sale and Price.

Now, Boston is in purgatory. Owner John Henry is insistent on getting below the luxury tax and the Red Sox probably do not have the funds to extend Mookie Betts on that basis alone. There is a reason that the two sides have never seen eye to eye: Betts knows his value, and they do too… but they cannot match that value.

Simultaneously, the Red Sox have an aging rotation (sound familiar?) and very little wiggle room especially after Martinez declined to use his opt-out clause, all but guaranteeing bold moves from Boston to clear out payroll.