The Case for Trading Paul Skenes

Let's make a case.

Paul Skenes threw his first career complete game last Sunday against the Phillies, surrendering just one run over eight dominant innings. He also took the loss. The irony wasn't lost on baseball Twitter, where discourse immediately split between lamenting Skenes getting deGromed and rival fanbases half-jokingly suggesting the Pirates should trade their ace.

Jon Heyman reported Wednesday there's "No chance, no way, no how" the Pirates would consider such a move. But an idea that sounds like it came from a Nico Harrison think tank session might not be as insane as it appears. Let me walk through why a Skenes trade could make sense for all parties involved.

The Bob Nutting Problem

Bob Nutting paid $92 million for the Pirates in 1996 and has since become one of baseball's most despised owners. The numbers tell the story of nearly three decades of organizational penny-pinching.

Pittsburgh's biggest free agent signing was Francisco Liriano's three-year, $39 million deal in 2015 — which they promptly traded away after just 1.5 seasons, meaning they never actually paid out the full contract. Their largest extension went to homegrown outfielder Bryan Reynolds for eight years and $107 million in 2023. That's it. That's the list of significant financial commitments from an owner who's watched his franchise's value balloon from $92 million to Forbes' current estimate of $1.35 billion.

The Pirates have finished outside the bottom five in total payroll just three times in the last 15 seasons, with their highest finish coming in at 20th. We're talking about systematic organizational negligence spanning multiple generations of players and fans. Nutting has presided over one of the most sustained periods of competitive irrelevance in modern baseball history.

Everyone already hates Nutting. How much worse could trading Skenes possibly make it? At least a trade would signal some level of strategic thinking rather than the passive decay that's defined the Nutting era.

The uncomfortable truth is that Nutting has shown zero indication he'll suddenly open his wallet to build around Skenes. If anything, the owner's track record suggests he'll let the ace walk in free agency after 2029 rather than pay market rate for an extension. A trade, executed properly, could be the most competent move of Nutting's tenure.

The Front Office's Difficult Position

Most blame for Pittsburgh's talent-deficient roster falls on Nutting's penny-pinching, but Ben Cherrington and the front office are accessories to the crime. While they're clearly operating under budgetary constraints that would handicap any GM, their work in the draft has been frustratingly inconsistent for a team that can't afford to miss.

Cherrington took over prior to the 2020 season and immediately faced the COVID-shortened draft. His picks of Nick Gonzales (7th overall) and Carmen Mlodzinski (31st overall) deserve some grace given the unusual circumstances, though Jared Jones in the second round looks like a home run.

The 2021 draft, however, was a different story. The Pirates held the 1.1 pick and selected catcher Henry Davis out of Louisville, partially because the team knew he'd sign for below slot value — yet another example of ownership constraints affecting talent acquisition. The next three picks were Jack Leiter, Jackson Jobe, and Marcelo Mayer. While those three have all shown real promise, Davis is already entering bust territory just three years later.

Outside of Bubba Chandler (third round, 2021) who's knocking on the door of the big leagues after dominating Triple-A, the Pirates had far too many misses during that crucial two-year period. When you're operating with a bottom-five payroll, you simply cannot afford to whiff on premium draft capital.

Here's where a Skenes trade could actually bail out Cherrington's struggles. The GM surely points to the return Washington received from San Diego for Juan Soto as the blueprint. Similar to Pittsburgh, the Nationals had not particularly excelled in recent drafts. AJ Preller's ability to pump out top prospects in San Diego made the Padres the ideal trading partner. In 2025, James Wood, CJ Abrams, and MacKenzie Gore rank as three of the Nats top four players by WAR — each a budding star that have achieved rebuild cornerstone status.

Soto had 2.5 years of control when traded. Skenes has roughly 4.5 years. The return would need to be equivalent or better, but a package starting with players like Boston's Roman Anthony (baseball's #1 prospect), CF Cedanne Rafaela, and SS Marcelo Mayer represents the caliber that should start conversations. A trade executed at that level could instantly restock a farm system and major league roster that Cherrington's drafts haven't adequately replenished.

The Skenes Factor

Here's where understanding Paul Skenes the person becomes crucial. This isn't a diva superstar demanding a trade or a mercenary chasing dollars. Skenes is a no-nonsense competitor who gives everything to his current team. But consider what we've learned from similar situations.

Garrett Crochet referenced his desire to "run himself into the ground" for the team that gave him his payday. He nixed trades last season because he didn't want to risk injury before securing his financial future. The Red Sox recognized this dynamic, traded for Crochet, and immediately locked him up long-term. Now Crochet feels comfortable giving his all without fear of a devastating injury costing him hundreds of millions.

Skenes already has that winning mentality, but he's also smart enough to understand the business. A trade to a committed franchise could provide both the competitive environment he craves and the financial security he deserves. It's the difference between Shohei Ohtani's stardom with the Angels versus his stratospheric fame with the Dodgers just 50 miles up the 405.

The Current Pirates Reality

Let's be honest about Pittsburgh's roster. Beyond Skenes, O'Neil Cruz, the recently injured Jared Jones, and soon-to-arrive Bubba Chandler, this team lacks blue-chip talent. Bryan Reynolds, once a cornerstone, has been the Pirates' worst position player by WAR this season. The prospect pipeline needs restocking, and free agency isn't an option under Nutting's ownership.

A Skenes trade could provide the talent infusion necessary to build a sustainable winner— a path I do not believe currently exists over the next 5 years for this Pirates franchise.

The Uncomfortable Truth

Tim MacMahon reported that the Mavericks' Luka Dončić trade "probably will cost the franchise nine figures over the next several years." A Skenes free agency departure could cost the Pirates big time. How much of that Forbes $1.35 billion Pirates valuation is built on Skenes equity? My back-of-the-envelope math suggests low nine figures, considering his stature as arguably the game's most famous player alongside Shohei Ohtani and Aaron Judge.

The cruel irony is that Skenes' value to the Pirates as a public figure — enhanced by his relationship with Livvy Dunne and his status as a transcendent talent — makes him simultaneously more valuable to trade and more painful to lose. But letting him walk in 2029 for compensatory draft picks would be organizational malpractice on a scale that would make even Nutting's penny-pinching look competent by comparison.

Though the Pirates will likely hang on to Skenes and do the dance around a potential extenstion before ultimately trading him or letting him walk a few years down the line, a trade in the present is not as outlandish as it seems. And I completely understand why the Pirates are taking the stance now that there is no way or no how, but things can change rather quickly.

And hey, maybe they'll be lucky enough to land whatever baseball's equivalent of Cooper Flagg turns out to be in the MLB draft lottery. Funny enough, I think the easiest cross-sport comparison for that level of prospect is... Paul Skenes himself.