Cubs are about to tell us how long this rebuild will actually be

Frustrations with Jed Hoyer and the Cubs front office have reached levels not seen in a decade or more. Even then, as frustrated as fans were with a 101-loss 2012 team, but Theo Epstein made what to expect abundantly clear when he came in and assumed control: a period of pain, followed by sustained success and a shot at that coveted World Series championship.

Since he delivered on that promise back in 2016, Chicago remained an annual postseason contender until last summer, when a double-digit losing streak spelled the end of an era and Hoyer jettisoned Kris Bryant, Anthony Rizzo, Javier Baez, Craig Kimbrel and others, setting off the start of another rebuild.

Now, the Cubs find themselves firmly entrenched as sellers once again, entering Monday’s off-day at 28-45 – 13 games back of the first-place Cardinals in the NL Central. How Hoyer approaches the trade deadline this time around, though, could be even more telling than the moves of last summer.

Willson Contreras is as good as gone. That doesn’t mean the Cubs can’t turn around and bring him back in free agency this winter, but there’s been no signs of any sort of in-season extension that would keep him on the North Side past the deadline. The same can be said for the team’s veteran relievers – namely closer David Robertson and fellow right-handers Mychal Givens and Chris Martin.

But there’s one guy we’re hearing will be made available that could signal a lengthy rebuild, rather than a quick right-the-ship re-tooling this whole spiel has been billed as since last July and that’s Ian Happ.

Unlike Rizzo, Baez and Bryant a year ago or Contreras this time around, Happ isn’t in his walk year. He’s under team control through 2023 – meaning there’s no sense of urgency to move him (or, at least, not because he’s set to walk at year’s end; you can still make the case there’s a sense of urgency and it comes from his being in the midst of a career-best year).

Cubs: Trading Ian Happ and also winning in 2023 would be a challenge

If the Cubs send their switch-hitting outfielder packing in the next month, along with Contreras, it will subtract the team’s two most valuable position players from the equation, throwing a gut punch to a roster that is, very clearly, several levels beneath being even a postseason contender, let alone a team with World Series aspirations.

Happ has ridden the ups and downs during his career but it looks like the former first-rounder has come out all the better for it. He’s slashed his strikeout rate dramatically, become a very dangerous hitter from the right side of the plate and flashed the leather regularly in the outfield this season.

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It would be a tough high wire to walk – trading Happ while telling fans the team plans on competing again as soon as next season. That’s not to say it would be impossible, but the front office and ownership would have their work cut out for them. So while it’s not a guarantee, an Ian Happ trade could signal we’re in for a lengthier rebuild than we expected to this point.