Jed Hoyer Needs to Walk Line Between Aggressive, Reckless at Deadline

The trade deadline looms just 10 days away and there has to be any significant player movement as teams jockey for position. While it’s not abnormal by any stretch to see most of the action confined to a very small window just ahead of zero hour, all indications were that the Cubs would try to get ahead of that crunch. They may have been trying for some time now to do exactly that, but various circumstances are conspiring against them.

Chief among those is the Diamondbacks’ reluctance to wave the white flag and start trading off their expiring contracts. That means Eugenio Suárez, the most sought-after power hitter among those who could be available, isn’t being openly dangled. The same goes for righty starter Joe Ryan of the Twins, as Minnesota still has two more years of relatively cheap control and might not want to punt them away even if this season looks like a lost cause.

When demand is high and supply at the top end is low, prices for the lower tier(s) of available players are inflated. That’s the tightrope Jed Hoyer has to walk as he looks to make necessary improvements to his roster for the postseason without emptying out the farm system for future seasons. He’s said no one is untouchable, a common mantra dating back to Theo Epstein’s leadership, but the key is to find ways to get better without overpaying for what might end up being only incremental upgrades.

Owen Caissie stands out as a great example. Voted as the “Prospect Most Likely to Be Traded” in a survey of more than 40 MLB executives conducted by The Athletic’s Jim Bowden, many believe Caissie will be used to land a pitcher at the deadline. The concern from the fans’ perspective is that the power-hitting outfielder will end up bringing back just a rental arm, which is probably unfounded.

Hoyer isn’t going to move Caissie just for the sake of moving him, especially with Kyle Tucker expected to test the market after this season. But if the Cubs can use the ginger Canadian to headline a package that addresses multiple needs and/or brings them a starter with multiple years of control, they have to consider it. Ryan fits that mold, as does Mitch Keller of the Pirates.

We recently took a look at Keller’s potential fit with the Cubs, though I can’t see Hoyer being cool making him a one-for-one swap with Caissie. That said, I can definitely envision a scenario in which the perceived cost for one or more Cubs trades is higher than the return.

Hoyer has to think of himself kind of like Kevin Bacon in Footloose, except he might want to check his shoelaces before climbing aboard the tractor. Or maybe he needs that extra boost of intentional ballsiness to stare down his colleagues in a game of trade chicken until they are the ones who blink. Knowing Tucker could be gone at the conclusion of the season provides more impetus than usual to take big swings.

It may take until October to know whether Hoyer makes loud contact or whiffs, but we’ll know just how aggressive he’s willing to be much sooner. In other words, it’ll be like watching a Cubs game on Marquee and following along on the MLB app at the same time. Which is to say the latter will tell you what happened quite a bit earlier.

All we can do in the meantime is sit back and sift through the rumors until deals really start getting done. And once they do, something tells me Hoyer is going to push enough chips in to make a not-insignificant portion of the fanbase question whether he’s lost his mind.