The Pittsburgh Pirates have been one of the most active teams this offseason, and it’s no mystery why. They’re building around Paul Skenes - their Cy Young winner, their ace, and, frankly, the kind of pitcher teams dream of anchoring a rotation.
But with all the moves they’ve made, the pressure is on. If the Pirates can’t take a major step forward this season, they may be facing a harsh reality: Skenes could want out.
And if it comes to that, the Pirates might be forced to consider something bold - something that could reshape the franchise: trading Skenes while his value is sky-high.
One potential trade partner that stands out? The Los Angeles Dodgers.
It’s a team with the resources, the win-now mentality, and the kind of young talent that could make a deal worthwhile for Pittsburgh. And at the center of that hypothetical return package?
Roki Sasaki.
Now, let’s be clear - this isn’t a move anyone in Pittsburgh wants to think about. Skenes is the kind of pitcher you build around, not trade away.
But baseball’s a business, and if the Pirates can’t convince him they’re serious about contending, they’ll have to weigh their options. Skenes is entering his age-24 season, and with four years of club control remaining, his trade value may never be higher.
If it becomes clear he won’t sign long-term, Pittsburgh has to at least listen.
Enter Sasaki - the electric right-hander from Japan who just wrapped up his rookie season with the Dodgers. His regular-season numbers were a mixed bag: a 1-1 record, 4.46 ERA, 28 strikeouts, and a 1.431 WHIP over 36 innings.
But that’s only part of the story. In the postseason, Sasaki flashed the upside that made him such a highly touted international signing.
He stepped into a high-leverage bullpen role and thrived, posting a 0.84 ERA, six strikeouts, a 1.031 WHIP, and three saves across nine appearances. That kind of performance under playoff pressure doesn’t go unnoticed.
Sasaki still has years of team control and the kind of raw stuff that suggests he could develop into a frontline starter. Pair him with Bubba Chandler - another high-upside arm in the Pirates’ system - and suddenly Pittsburgh could have a young, dynamic one-two punch leading their rotation for years to come.
Of course, there’s no sugarcoating what it would mean to move on from Skenes. You don’t just replace a Cy Young winner overnight.
His presence on the mound, his leadership, his ability to shut down any lineup in baseball - that’s not something you give up lightly. But if it becomes clear that he’s not planning to be in Pittsburgh long-term, and if the return includes a talent like Sasaki plus multiple impact bats, the Pirates could be looking at a deal that resets their timeline without starting over.
It’s a tough pill to swallow, but it’s also the kind of decision that separates smart front offices from the rest. If Skenes wants to win - and if the Pirates can’t provide that stage soon - then flipping him for a package that includes Sasaki might just be the most forward-thinking move they can make.
For now, Pittsburgh is still in win-now mode. But the clock is ticking.