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

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. 

Chicago Cubs: Time to rebuild the farm

The Red Sox depleted the farm in the pursuit of a championship. The Cubs did the same in the hopes of staying on top. Now both are in dire need of premium prospects.

There is a real possibility that Boston’s own window is on the verge of closing. Betts is likely to be gone next winter if not this offseason, and the sheer lack of arms in the minors will doom them after the way this past season went, especially if Sale eventually needs surgery.

Henry and the Red Sox are very cognizant of this, which is why they fired Dombrowski (just one year after winning the World Series) and hired Chaim Bloom–a former Rays executive and master of navigating payroll or lack thereof–to take his place.

Theo is almost certainly cognizant of how this applies to him, as well. With Ricketts insisting the Cubs should be competitive without windows and Epstein’s contract expiring after the 2021 season, it makes sense that there has been so much talk about change and restructuring.

Baseball is a copycat league. If Theo cannot find a way to acquire assets for the future while remaining competitive, then his days in Chicago are numbered.