Two back-to-back Cy Young winners in the same rotation has never been done. Not by the Yankees in their prime, not by the early 2000s Braves, not by anybody. The Pittsburgh Pirates could be the first team in baseball history to do it — if Ben Cherington actually picks up the phone.
Tarik Skubal just returned from elbow surgery in just over five weeks instead of the usual two to three months. The procedure removed a loose bone chip using a less-invasive NanoScope technique. He didn’t miss a beat. The Tigers are mired in last place in the AL Central, nearly 10 games out of the division, and Jeff Passan at ESPN has him at 85% trade probability and ranked #1 on the deadline candidates list. Passan called him “the dream deadline candidate, the sort of ace who can carry a team in the postseason.” The Dodgers are interested. So are the Yankees, Braves, Brewers, Blue Jays, and Rays.
Pittsburgh is sitting at 39-40, hovering 1.5 games back in the NL Wild Card race, with a bullpen that posted a 6.40 ERA in June. Six. Point. Four. That’s the thing keeping this team out of the postseason — not the rotation, not the lineup, not Paul Skenes, who is sitting at a 2.85 ERA with a 0.93 WHIP this year. The bullpen is actively bleeding games every week.
And the prorated cost for Skubal for the rest of 2026? About $10 million. For a back-to-back Cy Young winner who missed just over a month of a season and came back healthy. Before his next contract hits — which everyone expects will be at least $400 million — you can get him for the price of a decent free agent reliever.
"If the Tigers decide they're going to trade Tarik Skubal, yeah, I'm watching the Braves."@Buster_ESPN on Cellini & Dimino says Atlanta is one of the teams to watch if the reigning Cy Young winner becomes available at the deadline.
Would you trade the prospects to bring Skubal… pic.twitter.com/rZbe13yUpW
— 680 The Fan (@680TheFan) June 22, 2026
Skubal himself has already looked his teammates in the eye and told them: “The future for a lot of people in this room — not just myself — the outlook could look very much different in two months, and it all comes to an abrupt end.” He’s an ace who understands his situation and isn’t hiding from it. You don’t often get that clarity from a player heading into a trade deadline.
I understand the hesitation. The 2024 deadline is still a fresh wound. Pittsburgh bought at the deadline — De La Cruz, Kiner-Falefa, a handful of arms — and then went 8-19 in August and fell completely out of contention. Spending capital and getting nothing for it burns. The fanbase hasn’t forgotten.
But that’s not an argument against buying. That’s an argument against buying badly. Acquiring a bunch of peripheral pieces and calling it a playoff push is different from going and getting the best available pitcher on the market.
The knock everyone makes about Pittsburgh and rentals is valid: you trade for Skubal, he walks after October, you just donated two prospects to the Tigers. CC Sabathia did this to the Brewers in 2008 — pushed them into the playoffs and bolted the same winter. But the Brewers made the playoffs. That’s a thing that happened.
This roster, with Skenes at the top and Skubal behind him, is genuinely built to compete in October. A five-game series against anybody with those two going back-to-back is not a comfortable situation for the opponent. The problem isn’t the front of the rotation. It’s that by the time a game gets to the sixth inning, Pittsburgh’s bullpen has a better than average chance of collapsing.
Cherington has been a seller at five of his six deadlines running this franchise. He is not wired to be aggressive. Every previous offseason has come with the caveat: we’re building toward something. The Pirates signed Konnor Griffin to a nine-year, $140 million extension earlier this year — they believe in their foundation. Skenes has been a legitimate ace since day one.
The window that Cherington has been building toward is, right now, open. Not “opening.” Open.
If he stands at the August 3 deadline with prospects still intact and the Pirates still one and a half games out of a playoff spot, someone is going to need to explain what all of this was for.
