Lemon Shakeup: How Should Cubs Address Flawed Organization This Winter?

The headline is a question because, well, I’m genuinely curious as to how exactly the Cubs will go about reshaping an organization that has fallen into disrepair. To borrow from the parlance of our comments section, they could use either a chainsaw or a scalpel (I’ll spare you a personal anecdote there). Or perhaps we should embiggen the metaphor to ask whether they choose to redecorate, strip to the studs and renovate, or raze and rebuild.

In the interest of time, and because a lot can still happen in the remaining 20 games and beyond, we’ll go ahead and rule out the final option. Ownership has way too much money invested in the local infrastructure to sit through another few moribund years that will cost them them at least as much in external revenue as it does at the gate.

And while we’re at it, we can probably go ahead and rule out the notion that simply reupholstering the furniture and hanging new drapes is going to do any good. Not if they’re again given a budget that makes even Big Lots seem like a luxury destination. All that talk about edge and urgency and improvement from within put the Cubs right back in the same position as last year, with a broken offense and no gas to get them across the finish line.

You want to see what urgency looks like? The Yankees let Joe Girardi walk at the end of his contract — following a season in which their 91 wins marked a five-year high — because they felt they could do better. So they hired Aaron Boone out of the ESPN broadcast booth and won 100 games in 2018. They’re at 94 wins as of post time and their .653 winning percentage is 36 points higher than last season.

Or you could look to Boston, where baseball ops president Dave Dombrowski was fired less than one year after winning the effing World Series. They’re so manic about competing at the highest level that missing the playoffs after boatracing the league the previous season led to them sacking one of their top execs.

Direct lines could be drawn from those situations to the Cubs, particularly in the case of a guy named Joe not being brought back after a successful run, but that’s not really the point here. Especially not if you’re trying to say that Girardi should replace Maddon. It’s more about the idea that big-market teams have and should shaken things up when they feel they’re not getting lemonade from their lemons.

Barring a miraculous run like something out of Major League or The Mighty Ducks, Maddon probably won’t be the guy to shepherd this team in 2020 and beyond. With all due respect for how much he’s done over the last five years, you can’t run a team based on nostalgia. And when the wins aren’t coming as frequently, it’s easier for your eyes to drift to the peeling paint and warped laminate that have actually been there the whole time.

It’s on the players to perform, no doubt about it, but when that performance was supposed to have been improved by more direct hands-on coaching from the manager, well…

There’s also plenty of blame to be laid at the collective feet of the front office, which whiffed badly on the acquisitions they made heading into the season. Limited budget or no, they very literally got less than nothing out of Daniel Descalso and Brad Brach while failing to meaningfully address obvious issues with their roster construction. And this came after Theo Epstein’s impassioned speech about spending all their energy to fix what broke.

While the Cubs’ baseball executives have no doubt spent a great deal of time and effort trying to acquire talent within the parameters they were given, they did it while running on a treadmill rather than out on a trail. They may have worked up a lather, they just didn’t go anywhere. Does that mean the Cubs need to make like the Red Sox and clean house at the top? Not necessarily, though the guys pulling the strings need to do a much better job this winter.

Considering all the factors involved, it’d be nearly impossible for them to not do better. Between the incredibly low bar they’ve set for themselves, the expiration of several significant contracts, and the injection of revenue from Marquee Sports Network, the Cubs have no reason to be quiet this winter. Unless, that is, Tom Ricketts further constricts the budget after getting little return on this year’s increased payroll.

A lot of the “renovation” of the roster will take place out of necessity, with Cole Hamels and Ben Zobrist no longer under contract and several other players unlikely to be brought back in any sort of significant role. That could give the Cubs the motivation to pursue someone like Gerrit Cole, who’s going to cost a ton but would be the ace they no longer have.

There’s been a lot of talk about big trades, which could certainly be part of the plan moving forward. Much of the focus has been on Kris Bryant potentially being moved, though a lot of that comes because his name moves the needle. It’s probably more likely the Cubs would deal someone like Victor Caratini, who significantly boosted his value and could be worth more to the team in a trade than he is languishing in a backup role.

Or they go the other direction and move Willson Contreras out of concern that his injury history could continue to the point that he’ll age out of his superior athleticism more quickly than his peers. There’s also the distinct possibility that the Cubs part with a combination of Addison Russell, Ian Happ, and Albert Almora Jr., none of whom have established themselves as consistent contributors.

Kyle Schwarber could find himself among that group as well, though a continuation of his performance since the start of August makes him far less expendable than before. Of course, that could depend on how the Cubs proceed with Nicholas Castellanos, who has been a revelation since coming over from Detroit. He’s increased his value a great deal, though, and he’s young enough to cash in big-time. Pursuing Cole probably means letting Castellanos go elsewhere.

Wow, I’m a thousand words into this and there’s still so much ground to cover that I’m better off just cutting it short. Not only is there still a lot of baseball to be played, but the landscape is going to change dramatically in terms of what the Cubs and other teams are looking to do between now and the time moves can be made. And as I said at the start, this was really a matter of setting some things up for the next few months.

Rather than putting a poll here at the end, I’ll go against my better judgement and invite your thoughts on the offseason. Do the Cubs need to move on from Maddon? What about members of the front office? Do they need to trade any big names, or just part ways with the fringe guys while signing another superstar or two? So many questions, many of which I see are already being answered over at The Rundown.

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