Although the Cubs have been and will be prominently connected to a huge trade candidate like Tarik Skubal, it’s important to remember that the team’s play and projection has to justify such a huge move come the Trade Deadline. Right now, for example, you just could not justify the Cubs shipping out a massive haul of talent for a couple months of Skubal when the Cubs might not even make the playoffs.
Chicago Cubs President Jed Hoyer adds another layer of consideration to that calculus, as relayed by Jesse Rogers:
Jed Hoyer on trade deadline aggressiveness: “Your World Series odds are probably going to be correlated to your odds of getting a bye and getting a bye is such a big deal…A lot of that aggressiveness is based on that ability to get the bye.” 1/2
— Jesse Rogers (@JesseRogersESPN) June 5, 2026Even though a wild card-ish team could desperately need him more than a 1st place team, it's the one in first that might land him. In other words, the Cubs need to get moving up the standings if they want to add in a big way! 3/3
— Jesse Rogers (@JesseRogersESPN) June 5, 2026The World Series odds are such a driving force when it comes to doing harm to the future of your organization (which is, by definition, what these trades are: some level of long-term damage in exchange for near-term help). Sometimes, those odds are high enough to justify a major move; sometimes they are not. You try to play at the margins with what you include in a trade so as to limit the damage, of course, but fundamentally, you are putting some longer-term risk on the table. It has to be worth it.
And, to that end, Hoyer reminds us that it’s not just about the odds in a generic sense. It’s a real calculation, and it’s one that is informed MASSIVELY by that dang first round bye. If you have a top-two record in your league, then you automatically avoid a 50ish/50ish coin flip of an opening round. Your World Series odds, therefore, don’t immediately got chopped in half right out of the gate.
If you’re one of those teams – a team with a very good shot at being one of those teams – then you know (1) the impact a major piece like Tarik Skubal can have might be all the more prominent in the most important games a team can possibly play, and (2) losing long-term value for a short-term boost down the stretch and in the postseason is slightly more likely to be “worth” it in the end.
That is all to say, Jed Hoyer is not wrong. It makes sense for the teams with a shot at the bye to be the most aggressive at the Trade Deadline.
… but also, I don’t know that folks want to hear that right now. I think most fans understand what he’s saying, but also really want to see the Cubs make the postseason no matter what. And trades in July/August can help make that happen, regardless of the bye situation. So you would still want to see the Cubs make impactful moves if it meant a better shot at October baseball.
Still, I agree fundamentally that if you’re talking about a Tarik-Skubal-level move, I think the bye has to be at least in play. With a few games, perhaps. The Cubs are currently 7.0 games out of a bye spot.
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