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Drastic decisions Ben Cherington must make in 2026 to save his job for 2027

Much to the chagrin of Pittsburgh Pirates fans, Ben Cherington is still in the general manager's chair heading into 2026.

But he'll be under enormous pressure – not just from fans, but from ownership (even a passive owner like Bob Nutting) to prove that the rebuild that is now entering its seventh year hasn’t been a massive waste of time.

To save his job for 2027, Cherington has to stop rebuilding and start building. That means a mix of bold trades, aggressive spending, major staff overhauls and a clear commitment to either winning with the current core or resetting with purpose.