Dream Pirates plan for 2026 as Ben Cherington enters what could be final Winter Meetings

If this really is the winter that decides whether Ben Cherington keeps his job, then the Pittsburgh Pirates have arrived at the most dangerous place in sports: the crossroads between patience and revolt.

Fans don’t want “process” anymore. They want a plan –– a real one. Not another press-conference riddle about flexibility and internal options. If this is potentially Cherington’s final Winter Meetings as the man in charge, then his dream plan for 2026 isn’t complicated.

It’s bold. It’s uncomfortable. And for once, it looks like a franchise that realizes Paul Skenes’ arm has a ticking clock attached.

Pirates' dream plan for 2026 as Ben Cherington enters what could be his final Winter Meetings as GM

Step 1: Build around Paul Skenes like a serious franchise

The Pirates’ dream plan begins and ends with Skenes. This isn’t even about “developing around” an ace; it's about weaponizing him.

A good organization attacks its window the second it opens — not three years later when everyone is either traded or injured. Skenes doesn’t need motivation. He needs reinforcements.

The dream? The Pirates stop treating Skenes like a lottery ticket and start treating him like Max Scherzer in his prime. You don’t waste seasons of a generational arm by hoarding payroll space like it’s 2008. You spend. You support. You raid the market for the pieces that make October realistic, not aspirational.

Step 2: Fix the lineup for real (not "internally")

Pirates fans have listened to the same gospel for years –– "Oneil Cruz breakout," "Jack Suwinski bounce-back," "Henry Davis figuring it out" –– and guess what? All of that still needs to happen.

But the dream plan doesn't rely on all of that exclusively. The dream plan insulates it. Because serious teams don't need development miracles to survive as long as they supplement them.

The Pirates’ dream Winter Meetings involve adding a middle-of-the-order bat, a real first baseman who hits 30+ home runs, a left-handed on-base weapon and an everyday outfielder who actually scares pitchers. No lottery tickets or reclamation projects –– real hitters.

The dream is that the Pirates stop trying to win “efficiently” and start trying to win, period.

Step 3: The Mitch Keller moment

Every Pirates fan knows it’s coming. Mitch Keller is the most likely big trade chip this organization has had since Gerrit Cole, and the dream scenario isn’t clinging to him emotionally — it’s turning him into offense that lasts six years instead of pitching that lasts two.

This isn’t selling; it's upgrading. The dream plan is flipping Keller for a cost-controlled hitter who fits Skenes’ timeline, not keeping him just to finish third.

A real front office worries about windows –– and right now, the Pirates' window doesn't say "rotation depth." It screams, "score more than four runs."

Step 4: Spend like you know time is limited

The dream plan includes something Pirates fans barely recognize anymore: a contract with commas. Not a one-year flyer. Not a bounce-back hope story. Not a minor-league invite –– a real, uncomfortable-for-ownership contract.

Every team in baseball eventually faces this moment — the one where ownership decides if it’s in the business of winning or bookkeeping. If Cherington wants to survive past 2026, he needs to push that moment directly onto Bob Nutting’s desk and refuse to blink because the dream plan cannot exist without an actual budget.

Skenes isn’t cheap forever. If this team doesn’t invest before it gets expensive, then it will never invest at all.

Ultimately, this is Cherington's line in the sand. If the Pirates walk out of these Winter Meetings with a real bat, a real payroll jump and a real commitment to Skenes' window, then maybe Cherington survives this.

If not? Then 2026 won’t be remembered as the year the Pirates tried. It’ll be remembered as the year they had the best pitcher in the world and still acted small.