Key Points
Bullet point summary by AI
- An NL Central team appears to have already taken itself out of contention for one of the most sought-after pitchers ahead of the trade deadline.
- The decision stems from the team's current playoff positioning and a front office philosophy that demands clear postseason odds before making major moves.
- Without immediate upgrades, the team's starting rotation remains one of the weakest in baseball and its playoff hopes hang in the balance.
Assuming the Detroit Tigers are open to trading Tarik Skubal at the trade deadline, they'll have no shortage of suitors. Chicago Cubs fans have been dreaming of the possibility of being among those in the running, and the fit almost makes too much sense given the team's glaring need for starting pitching and desperation to finally break through in the NL playoffs. Not only have injuries run rampant, but it feels like every starter the Cubs have turned to this season, not named Ben Brown, has been a disappointment.
The problem, though, is that Jed Hoyer — the man who'd be responsible for a Skubal trade to Chicago, if one were to go down — made it seem unlikely that such a deal would be made with where the Cubs stand right now. Just look at what he had to say about his willingness to be aggressive at the deadline.
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, 2026
Why the Cubs might already be out of the Tarik Skubal deadline sweepstakes
Hoyer says that the Cubs' aggressiveness at the deadline will be determined by their odds of receiving a first-round bye in the postseason. Well, Chicago's most recent loss, an 18-3 shellacking at the hands of the Giants on Friday, has them sitting at 33-31 on the year, 6.5 games back of the first-place Brewers in the NL Central and 8.0 games back of the Dodgers.
These gaps aren't insurmountable in early June, but what are the odds the Cubs will be in a position to go for a bye come the deadline with how they've been playing? Probably slim. If so, the chances of the Cubs trading what it'd take to acquire Skubal, perhaps the most expensive deadline rental in recent memory, are practically zero.
That reality is a hard one to accept.
Jed Hoyer's conservative deadline mentality is bound to doom Cubs
I understand where Hoyer is coming from. If the Cubs aren't playing like a World Series-caliber team, it's hard to justify parting with immense prospect capital for just a couple months of a player who, you might not win a World Series with and whom you'd be unlikely to re-sign. The thing is, though, that a lack of action from a Cubs team that desperately needs starting pitching is likely to doom their season.
Pitcher | Starts | ERA |
|---|---|---|
Shota Imanaga | 13 | 4.74 |
Jameson Taillon | 12 | 5.13 |
Edward Cabrera | 11 | 4.99 |
Colin Rea | 10 (13 appearances) | 4.59 |
Matthew Boyd | 5 | 6.00 |
Ben Brown | 5 (17 appearances) | 1.92 |
How can Chicago expect to be competitive when this is their rotation? The Cubs have a 4.89 rotation ERA, the second-worst in the sport (better than only the Rockies). Most of the pitchers above are only struggling even more of late, except for Brown, who continues to be brilliant no matter how the team uses him.
It's not like the Cubs have much to look forward to, either. Cabrera struggled mightily in his return from the IL. Boyd isn't far behind, but who knows what to expect from him when he returns from his second IL stint of the season? Cade Horton is already out for the year, and who knows whether Justin Steele can pitch at all? Even the Cubs' top pitching prospect, Jaxon Wiggins, is hurt.
Hoyer is making it clear that Chicago will only make meaningful additions if they gain a ton of ground over the next month or two, but it's hard to see the Cubs making up that ground without Hoyer adding to this rotation in a meaningful way. This essentially sums up the pickle the Cubs are in.
We've seen Jed Hoyer fail miserably at deadline with similar mentality
Look no further than 2025 to find a disappointingly conservative Jed Hoyer trade deadline. The Cubs were in the thick of the NL Central race with the Brewers, so the fan base had reason to believe Hoyer would go all-out to improve the roster. Instead, he wound up acquiring guys like Andrew Kittredge, Willi Castro and Michael Soroka, none of whom were highly sought-after. Hoyer was uncomfortable meeting high asking prices for true needle-movers.
Of course, the lackluster deadline came back to haunt Chicago, as the Cubs wound up ceding the NL Central to Milwaukee and then losing to those same division rivals in the NLDS.
Hoyer was unwilling to part with anything meaningful when the Cubs actually had a shot at a bye, so fans can only cringe thinking about what this year's deadline will look like barring a sudden turnaround. While a Skubal trade might be on the extreme end of things, the likelihood that Hoyer refuses to make a single big move, robbing the Cubs of an increased opportunity to get back to the postseason, is frustrating.
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