Bernstein: Should Epstein Have Seen This Coming?

(670 The Score) Forgive Theo Epstein if he has the voice of David Byrne echoing in his head right now asking, "Well, how did I get here?"
It's unlikely the Cubs president of baseball operations foresaw his current position, trying to clear payroll room to extend his team's competitive phase, possibly by trading away a generational talent for a package not close to commensurate value. Even someone as aware as Epstein couldn't have signed his five-year extension in September 2016 envisioning himself shopping at the Rule 5 rummage sale just three seasons later and trying to reconstruct a bullpen with castoffs and upside bets.​

He never would've imagined being on what's essentially his third overhaul of a coaching staff in three years, with new organizational infrastructures necessitated for both hitting and pitching, David Ross as the manager and somebody other than Jason McLeod in charge of the amateur draft.

The changes to MLB's scouting and development catalyzed by independent thinkers outside the game have left the Cubs scrambling to catch up and keep up, even now.

It would be fair to point out that the executive who has told us he opens meetings by asking "What don't we know?" should be responsible for not getting behind any curve in the first place, after earning a reputation for always being at the vanguard. In other words, anticipating these things is the job.

Epstein has called it the "winner's trap," the phenomenon of assuming current practices are the best ones because of on-field success instead of trying to predict how to be ready for the next material evolution.  

And now it has left him to untangle himself from a mess of decisions gone wrong and value that withered on the vine. He committed millions to Jason Heyward, Tyler Chatwood, Yu Darvish and Craig Kimbrel, and he dealt what became three rising MLB stars for Aroldis Chapman, Wade Davis and Jose Quintana. Addison Russell has been cut, Albert Almora was demoted and Kyle Schwarber's growth has plateaued.

Most importantly and perhaps in part because of that track record, Epstein won't have the chance to buy his way out of it.

It's possible owner Tom Ricketts is content enough with one World Series title to make spending into the luxury tax a non-starter, even as he points to a top-five salary outlay as a sign of full commitment. It's clear enough from the tortured euphemisms that describe an obvious austerity plan that Ricketts now wants to hang onto more of his money instead optimizing his chances of winning at the cost of being only slightly less profitable. And it's despite his long-planned proprietary television network coming online.

Epstein was given the resources to modernize the training technology, outfitting his new lieutenants with the highest-tech shiny gadgets for advanced kinesiological study of swings and pitching motions, but he won't be able to use such funds for either free-agent talent or market-level extensions for all of their star players. Though Epstein oversees a more accomplished Cubs operation than any that preceded his, a confluence of circumstances has him working under new constraints.

Same as it ever was.

Dan Bernstein is a co-host of 670 The Score’s Bernstein & McKnight Show in midday. You can follow him on Twitter @Dan_Bernstein.