It’s a pivotal trade deadline for the Pirates — but are they willing to all-out sell?

Pittsburgh Pirates ace Paul Skenes blanked the best-record-in-baseball Detroit Tigers on Monday, tossing his third scoreless start this month and lowering his league-leading ERA to 1.91.

Yet the attendance at PNC Park was roughly half the season-high crowd on hand two nights prior to procure a bobblehead and loudly petition owner Bob Nutting to sell the team.

Advertisement Such is the state of Nuttings last-place ballclub a week before the trade deadline.

After wasting Skenes sensational rookie season last year, the Pirates have fully capsized in what could be his first Cy Young season.

Despite sweeping the Tigers, the Pirates are 19 games under .500 and firmly sellers ahead of the July 31 trade deadline.

How aggressively theyll sell is being debated around baseball.

The stakes have made it a defining week for Ben Cherington.

If the sixth-year GM is on the hot seat , as many in the industry believe, it could be his last chance to chart a course toward contention in 2026 that persuades Nutting to give him another year.

Nuttings comments upon firing manager Derek Shelton in May suggested his patience was wearing thin: We need to act with a sense of urgency and take the steps necessary to fix this now to get back on track as a team and organization.

Its been a decade since the Pirates reached the postseason, nine years since they finished better than fourth place in their division, and seven years since their last winning season.

Difficult as any GM might find it to construct a contender on a bottom-five budget, Cherington signed up for that challenge.

He so far has failed to win on Nuttings terms and replicate the successful low-payroll model of the Tampa Bay Rays, Cleveland Guardians and Milwaukee Brewers.

While the downfall of the previous Pittsburgh front office, led by Neal Huntington, was its inability to push pitching prospects to their full potential, the Cherington regime has failed to develop enough homegrown hitting.

The Pirates rank last in the majors this season in runs, homers and OPS.

The lack of run support explains why Skenes Cy Young resume currently features a 5-8 record.

The organizations best position player in the minors, 2024 first-rounder Konnor Griffin, is three levels from the majors.

Advertisement Cheringtons only viable path to upgrading the lineup by next spring is via trade.

(The Pirates havent signed a free-agent hitter to a multi-year deal since John Jaso in 2015.) As Cherington considers the possible roadmaps for fielding a winning team in 2026, here are a few ways his trade-deadline maneuvering could progress listed in order of escalating aggressiveness and what it would mean for the franchises future: Option 1: Rentals only On the move: UTIL Isiah Kiner-Falefa, LHP Andrew Heaney, OF Tommy Pham, LHP Caleb Ferguson Savings for 2026: None The upshot: This result would be a sign the Pirates were unwilling to lower their demands on players under club control beyond 2025, namely starter Mitch Keller and closer David Bednar, who are healthy and rolling.

On one hand, thats a reasonable approach; buyers are exceedingly reluctant to part with top prospects, and the Pirates would rather not trade core players for multiple mid-tier prospects.

However, other than saving about $6 million in 2025 salary, dealing only rentals would mean the Pirates are determined to run it back in 2026 with a similar roster.

Maybe theyd move a pitching prospect for a bat in the offseason.

Maybe not.

And maybe by then Nutting will have decided to let a different GM call the shots.

Likelihood: 25 percent Option 2: Opening the war chest On the move: RHP Mitch Keller, RHP David Bednar, RHP Dennis Santana and rentals Savings for 2026: About $27 million The upshot: Cashing in on the depth of their pitching reserves and capitalizing on having several of the most coveted arms on the market, the Pirates would swap a proven starter and two leverage relievers for a handful of young hitters.

They might not get any top-100 prospects in return, but the sheer volume would instantly increase the talent in their pool of position player prospects.

They could backfill Kellers and Heaneys rotation spots with prospects at Triple A Bubba Chandler, Thomas Harrington, Hunter Barco and spend the savings this offseason further strengthening the lineup and rebuilding the bullpen.

Likelihood: 35 percent Option 3: The arms and the Gold Glove On the move: 3B KeBryan Hayes, Keller, Bednar, Santana and rentals Savings for 2026: About $34 million The upshot: Two things can be true about the $36 million in guaranteed money remaining on Hayes contract: Its far more than the Pirates would prefer to pay for his light production with the bat, and its not a number most contenders would balk at paying one of the best fielders in the sport.

Even with Hayes OPS sitting below .600 for the second consecutive season, the Pirates may see this as a prime opportunity to offload his contract while doing no harm to their offensive outlook for 2026.

Likelihood: 30 percent Option 4: The great reallocation On the move: OF Bryan Reynolds, Hayes, Keller, Bednar, Santana and rentals Savings for 2026: About $48 million The upshot: If Cherington rises to this level of aggressive sell-off, it would suggest that either Nutting directed him to dump long-term salary Reynolds, Keller and Hayes are signed to the three largest contracts in club history or that the owner is so unwilling to add payroll for 2026 that Cherington felt he had to force financial flexibility.

Trading Reynolds while hes at a low point in value offensively and defensively would achieve very little beyond savings.

While the Pirates have the depth to replace a few pitchers, its hard to imagine that even with some operating room below Nuttings payroll limit Cherington would be able to meaningfully improve at third base and right field, upgrade other weak spots in the lineup (shortstop, left field, catcher) and sign a couple late-inning relievers.

Likelihood: 10 percent Seven months ago, at the Winter Meetings, Cherington remarked, If you look at Cleveland, Tampa and Milwaukee, yes, theyre getting value out of the draft.

Yes, theyre getting value in international (signings).

But the trades are a big piece of how those teams are built.

Trades are harder emotionally.

Everybody celebrates a draft pick when you make it.

Its all upside.

Right? But trades, theres a give and take.

Youre giving something up, so its a different emotional, psychological decision and experience.

Advertisement But to win in Pittsburgh were going to have to be willing to embrace that as those competitive teams have done.

Weve got to be open to it.

Cherington has another chance this week to embrace that give and take.

Thus far, his trading history in Pittsburgh has received poor grades; the paucity of impact players he acquired when trading away numerous veterans early in his tenure remains a frequent talking point among disappointed fans.

This week, Cherington cant afford to miss.

The phone calls started during the All-Star break, with other GMs asking not only about rentals but about players Cherington had extended, anticipating theyd be part of the Pirates window of contention.

As the trade deadline nears, Cherington will make some of the most important decisions of his Pirates tenure.

For now, those calls are still up to him.

(Top photo: Justin Berl / Getty Images).

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