With the speculation of the Pittsburgh Pirates trading star Paul Skenes, there is no doubt that conversation around the league about which teams would likely send the largest package for the ace. While the likelihood of a Skenes trade out of the Pirates seems unlikely, there are executives in the MLB who have thought of blockbuster deals.
In the latest piece from Mark Feinsand of MLB.com, he spoke with many executives around the majors about the possibility of Skenes being traded after a frustrating start for Pittsburgh. One NL executive told Feinsand of a trade where the team sends Skenes to the Boston Red Sox, which Pittsburgh should possibly consider.
“One AL executive who doesn’t think the Pirates should trade Skenes now believes the return wouldn’t be markedly different if they decide to move him in 2026 or '27, though he acknowledged the risk of injury and/or underperformance that could alter Skenes’ value down the road,” Feinsand wrote.
“If they looked to trade him now, I think something like 1.5 times the Soto deal would be a starting point,” the NL exec told MLB.com. “The reality is that few teams have that many good players to trade. I guess the Red Sox could send [Triston] Casas, [Roman] Anthony, [Marcelo] Mayer, [Kristian] Campbell, and [Tanner] Houck, assuming they won’t trade their extended guys. Writing that down makes me think, ‘Hmmm, maybe Pittsburgh should make a call.’”
The Pirates should “push more chips” along Paul Skenes

After the Pirates fired manager Derek Shelton, there's no doubt the team is in flux, with the future needing to be planned out, and while some believe Skenes would bring a sizable trade package, is it worth it? Really, Skenes could easily be seen as the future of Pittsburgh, as one NL executive said to MLB.com that the team should “push more chips” in the team.
“I think the bigger question is: what’s the plan, and do their actions match their words?” the executive said. “If their intent is to compete during these prime years of Skenes — and Cruz, [Mitch] Keller, [Jared] Jones, [Bubba] Chandler, etc. — then they should push more chips in and back it up.”
“Their return would likely be as significant a trade return as we’ve ever seen,” an NL executive said. “Though I see little reason to do that before next Trade Deadline [in 2026].”
At any rate, the Pirates are currently 17-33, which puts them dead last in the NL Central as they start a four-game series against the Milwaukee Brewers on Thursday night.