Should Paul Skenes stay with the Pirates? That’s the million-dollar question circulating MLB right now. Yes, the Pirates haven’t officially hinted at moving their star pitcher, but speculation is heating up fast. Skenes, one of the most electrifying young arms in baseball, has the potential to reshape the franchise’s future, or someone else’s. And while trading a talent like Skenes might seem unthinkable on the surface, some insiders believe a blockbuster deal could be a strategic win for both.

Well, in the Pirates’ current landscape, it might just make more sense than it seems.

“The best thing for the Pittsburgh Pirates would be to move Paul Skenes when he has his most value. It’s a depressing reality,” ESPN’s insider Jeff Passan said on the Pat McAfee Show.

Well, the Pirates will retain control of Skenes through 2029, delaying his free agency until after that year. While you might not anticipate a trade this early, Passan expects multiple suitors to inquire as the 2025 trade deadline approaches. There’s a compelling case for the Pirates to consider a deal, given Skenes is currently in his best form.

Skenes is going with a 2.63 ERA and 53 SOs, which proves his mettle at the mound and might be the best chance for the Pirates to make the best deal out of him.

It is true that a trade involving Skenes this year would undoubtedly spark significant unrest. However, sooner or later, the Pirates will have to confront the hard truth. Because they need to rebuild the team from scratch! Hereon, the best the Pirates can do is to trade him for an unprecedented return. This will enable the Pirates to fetch a good amount, enough to restock the roster with as much young talent as possible.

The Pirates are not new to the trading of star players. Since taking control in 2007, the Pirates’ owner, Bob Nutting, has presided over multiple rebuilds and payrolls. For instance, stars like Tyler Glasnow, Austin Meadows, and Shane Baz were traded from the Pirates in 2018. And, this time, Skenes might also be skeptical of staying with the team.

The Pirates are not a winning team

For starters, the Pirates have struggled to gain traction, entering mid-May with a 14–29 record and occupying last place in the NL Central. This is surprising considering Paul Skenes is putting on a good show on the mound. But more than what Skenes can do, it is with their owners. Bob Nutting’s long-standing reluctance to invest in the roster is making the team suffer, and players like Skenes perish at the league’s bottom.

“What incentive does Paul Skenes have to extend with the Pirates when the Pirates haven’t shown the willingness from Bob Nutting all the way down, or the ability to bring in guys who are going to make this team better? The Pirates haven’t shown that they are worthy of a Paul Skenes extension at this point.”

Skenes is already showcasing why he’s one of baseball’s brightest young stars. His dominant pitching proves he has all the tools to excel at the highest level. His work ethic and poise under pressure reflect the mindset of a future ace. But the Pirates’ current organizational struggles are holding him back.

With only $90 million as the payroll for 2025 and ranked 26th in the league, the team lacks the supporting cast, playoff ambitions, and infrastructure that a player of Skenes’ caliber needs to thrive and reach his full potential. So, why would he stay back here when he can get a winning team and reach the postseason?

Hence, before Skenes hits a rough patch, the Pirates should press the trade button. For the team, they will have enough cash to rebuild, and for Skenes, a winning team will be in place. All these to be done before it gets too late!