Jed Hoyer Could Try to Thread Needle with Ballsy Sell-Buy Moves

Most of the talk so far has been about whether the Cubs would be buyers or sellers at the deadline, though there has also been a smattering of chatter about them trying to do both. Even as their hope grows a little brighter with each win, that kind of needle-threading combination of moves could be a very real possibility for Jed Hoyer and his front office. It would take a particular set of circumstances, but one mitigating factor could set up a wild deadline.

I’m speaking, of course, about the inability to extend a qualifying offer to Marcus Stroman. That’s something we discussed briefly several days ago, prior to the Cubs getting hot again, and I’ve explored it in greater depth on multiple podcasts more recently. While those conversations were more about who the Cubs were most likely to trade should they become sellers, the fact remains that they’ll get nothing in return if Stroman finishes the season in Chicago and then opts out of his deal.

Ken Rosenthal noted as much in a recent piece for The Athletic about what he’s hearing as the deadline approaches, saying the Cubs could try to keep Cody Bellinger — who can get a QO — and trade Stroman. That seems more likely if they stumble through the next five games, but a scenario exists in which it could happen even if they’re successful. This is where the needle threading comes in.

The first step is that a team like, say, the Orioles would need to get really aggressive with an offer for Stroman that includes a near-MLB-ready top-100 prospect who fills one of the Cubs’ gaps. Hoyer would then need to swing a separate deal that exchanges some of his minor-league depth for a controllable starter, even though it’s unlikely to be someone of Stroman’s caliber.

What’s funny about such a pair of deals is that it would probably put the Cubs in a worse position should they manage to make the postseason. As things currently stand, they’d be a dangerous playoff opponent with the triumvirate of Stroman, Justin Steele, and Kyle Hendricks atop the rotation. So while Hoyer might be able to improve his roster for the future with a buy-sell deadline, it could come at the expense of the present.

That’s pretty easy for most people to stomach, particularly those who actually want the Cubs to sell in a big way, but this team still has a chance to catch lightning in a bottle like the Braves did in 2021. As things stand right now, Hoyer is tasked with giving the Cubs as good a chance as possible to make a run over the next two months while also putting them in a position of strength for next season and beyond. Pretty easy, huh?

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