Tarik Skubal is the kind of deadline target that forces a front office to stop thinking in neat little boxes. He’s the best player on the market this summer, and the Cubs are the club most in need of pitching help. Put those two things together, and it’s no mystery why the rumors have kept circling.
For Cubs fans, the appeal is obvious. They’ve watched this team get exposed by thin pitching depth before, including last year in the NLDS, and the fear is that October could bring the same story again. That’s why the idea of a Skubal-sized swing has taken hold: not just another arm, but the kind of arm that changes the whole conversation.
Of course, this isn’t the sort of move Jed Hoyer usually makes in season. His deadline playbook has leaned more toward volume than splash, more fringe arms than franchise-altering bets.
There’s a reason to pause when reports link the Cubs to a southpaw this expensive. A trade like this comes with real risk, and the Cubs’ pitching staff has already been battered by injuries enough times to make anyone flinch.
But this is also the kind of player who can justify breaking from the usual script.
Skubal would be more than a Game 1 starter. He’d reset the entire playoff rotation and give the Cubs the most overpowering mound presence they’ve had since 2015 Jake Arrieta.
That comparison matters because Arrieta’s 2015 NL Wild Card Game against the Pirates still stands as one of the defining Cubs performances of the modern era. Before that game, he told Pirates fans via Twitter, "Whatever helps keep your hope alive, just know, it doesn't matter," and then backed it up with an 11-strikeout shutout in a winner-take-all game against a 98-win team.
That kind of certainty has been rare in Chicago ever since.
Skubal’s numbers explain why he’s the prize of the summer. The two-time reigning AL Cy Young winner has posted a 2.46 ERA and 2.43 FIP since the start of the 2023 season, a stretch that covers his last 564 innings. That production is why he’d cost a massive haul now and another huge one later in free agency.
And that’s the catch. He’d probably be too expensive for the Cubs to keep beyond this run, which would make this an all-in move aimed at 2026.
Still, if the goal is to stand up to the Dodgers and Brewers in October, star power matters. Skubal is the rare pitcher who can bring it.
In Other News...
Cubs Just Got Pulled Into Torontos Deadline Rotation Shakeup
Torontos deadline-day rotation shuffle has already sent ripple effects through the league, and the Cubs were pulled into the middle of it before the dust could settle. The Blue Jays moved quickly ahead of the Aug. 3 deadline, adding Jose Soriano from the Angels while also reshaping the staff with veteran arms, a sign they were prioritizing immediate stability as they mapped out the rest of 2026 and even looked ahead to 2027.
For Chicago, the bigger story is how this kind of deal changes the market around it. A club in deadline mode can turn one trade into a broader reset, and the Cubs now sit in the orbit of a Blue Jays rotation plan that could still keep evolving as Toronto weighs future moves involving its veteran pitchers. Even after the first wave of action, the way Toronto sorts out its staff may decide whether this becomes a one-off adjustment or the start of something bigger. [Read more 🡒]
Cubs Just Paid A Real Prospect Price For An October Push
The Cubs made a clear win-now move, parting with one of their better infield prospects to shore up the roster for the stretch run. Jefferson Rojas was sent to the Mets in a deal that brought back Clay Holmes and Tyrone Taylor, a transaction that signals Chicago is treating October as more than a distant goal and more like a window worth pushing through right now.
Holmes gives the Cubs a right-handed arm who is still on the injured list but getting close to a return, while Taylor adds experienced outfield depth for the final months of the season. It is the kind of trade that usually comes with an uncomfortable cost, and Chicago paid it by moving a player it had reason to value, betting the short-term upgrade will matter more than the long-term regret. [Read more 🡒]
Cubs Just Got A Surprising Deadline Opening They Still Needed
The Cubs still have not made a trade move, but they do have one of the more intriguing deadline paths to monitor as they poke around with Texas. The Rangers have shifted their approach enough to at least listen on some pitching, which has put Chicago in the mix for arms such as Nathan Eovaldi, MacKenzie Gore and Jacob Latz. For a club looking for help without blowing up its deadline, that kind of opening is worth watching closely.
Texas, though, has also sent a mixed message to rival front offices, which is part of what makes this whole thing feel so unsettled. Trade talks can turn quickly at this time of year, and the Cubs are weighing options in a market where the other side may not be nearly as available as it first seemed. [Read more 🡒]