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

Related Topics: Ben Cherington

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.