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Cubs Offseason Analysis: Should Jed Hoyer Tear Down and Rebuild?

With speculation that Theo Epstiein has left the Chicago Cubs in turmoil, should Jed Hoyer trade away the core and implement a full-fledged rebuild?
Jed Hoyer Cubs

Photo: Geoff Burke/USA TODAY Sports

After Theo Epstein stepped down as president of baseball operations and Jed Hoyer was named heir apparent, there’s been speculation that the Chicago Cubs will press the restart button this winter. The recent rumors of potentially non-tendering Kris Bryant and Kyle Schwarber validate this speculation. Theo Epstein stated the Cubs were in a “transitional state” well before he stepped down, so change was always imminent.

But I, like many Cubs fans, thought this transitional state meant choosing which of the core to trade and which to extend. However, every news piece coming from the Chicago Cubs the last two weeks, including Jed Hoyer’s introductory press conference, has indicated a full-fledged rebuild is imminent. And I’m here to tell you why that would be a mistake.

Theo Epstein Has Not Set the Cubs Up to Fail

To stir controversy, national media has perpetuated the narrative that Theo Epstein has left the Chicago Cubs in turmoil amidst his premature departure. But this is false, as I explained in detail here. Theo has actually set the Cubs up for future success.

  • He locked up both Yu Darvish and Kyle Hendricks to long-term, team-friendly deals.
  • Alec Mills and Adbert Alzolay showed mid-rotation ability and are under club control through 2025.
  • The farm system not only has three top-100 prospects, but has guys with significant upside.
  • And finally, the Cubs have virtually no long-term money invested.

What about this fact pattern indicates an organization set up to fail? None of it. But the media focuses too heavily on the payroll slashing, the trade rumors, and the early postseason exit to take any real look into the matter.

Sure, Theo Epstein and Jed Hoyer did not successfully extend Kris Bryant or any of the remaining core. I get it. But extending nobody is a hell of a lot better than choosing the wrong guys to extend. What would Cubs fans say if Epstein offered Addison Russell, Kyle Schwarber, or Albert Almora long-term extensions early in their careers? All three were pegged as future foundational pieces circa 2016. Now, one is in the KBO and two are potential non-tender candidates this offseason. A full-fledged rebuild would be necessary if the Cubs had long-term money invested in those "busts." But thankfully, that is not the case.

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The Cubs Will be Heavy Spenders Post-2021

As mentioned earlier, the Chicago Cubs are in an envious financial position after 2021. While it may not seem that way with the financial effects from COVID-19, a third consecutive offseason of cutting payroll and the rumors of non-tendering former MVP Kris Bryant make it a fact. Jason Heyward is the only player under contract that could be argued as a bad long-term investment (and I’d even rebut this). The Cubs’ total payroll obligations drop from $150.5 million in 2021 to $60.0 million in 2022. That said, the Cubs are hand-tied financially for just one more offseason.

Do you think this financial flexibility after 2021, the year almost the entire core hits free agency, is a coincidence? Nope. This is Theo Epstein and Jed Hoyer’s plan of “sustained success” coming to fruition. It's why a complete rebuild is not necessary. Honestly, the Cubs have been halfway “rebuilding” since 2019 by cutting payroll. If Theo and Jed would’ve offered long-term contracts the last two offseasons, the whole “doomsday” mantra would be justified. Quickly transitioning from one competitive window to another requires financial flexibility. Theo and Jed knew this. Without it, clubs have to tear down and start over.

Jed Hoyer Should Not Overvalue Prospects

Another reason the Cubs should avoid a complete rebuild is prospect unpredictability. Addison Russell, Kyle Schwarber, and Albert Almora not even remotely fulfilling their projected productivity embody this uncertainty. A general rule of thumb is that half the prospects projected as MLB starters will eventually bust. The Cubs were fortunate to have a success rate well above that 50% mark, so why would Jed Hoyer trade all those successes away and roll the dice on another set of prospects? For big market organizations like the Cubs, that’s not necessary. It's also just flat-out negligence.


Photo: Jonathan Daniel/Getty Images

Organizations such as the Tigers, Orioles, Angels, and Pirates have been rebuilding for the last five years. How’s that worked out for them? Full-fledged rebuilds almost never go as smoothly as the one Theo and Jed implemented in 2011. It’s a slippery slope, and one the Cubs should avoid. Sorry if I don’t believe the absurd mindset that trading for a bunch of unproven prospects better sets the Cubs up for future success than extending the All-Stars already in their organization.

The Cubs Should Still Trade Some of the Core

Just because I believe a full-fledged rebuild is imprudent doesn't mean I want Jed Hoyer to sit on his hands completely this offseason. The Cubs cannot and will not extend the entire core. But there’s a middle ground between trading and keeping everyone that is optimal. For example, trading two of Yu Darvish, Kyle Schwarber, Kris Bryant, Javier Baez, Anthony Rizzo, and Willson Contreras for a modest haul of close-to-ready prospects puts the Cubs in a better position in 2022 and beyond all while not pressing the restart button entirely. Instead of trading everyone and relying solely on prospects for future success, the Cubs keep a few proven All-Stars in addition to stockpiling more young talent. This essentially hedges their bets.

The idea that the Cubs are better off trading every player who's responsible for the best six-year stretch in the organization's history is truly dumbfounding. Do we not remember Cubs baseball prior to 2015? As Michael Jordan stated after he won his fifth title in 1997, it was a perpetual rebuild. Let's not pivot back to the "lovable losers" stigma. I'd rather the Cubs keep winning the NL Central and making the postseason.