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. Anything less, and 2026 will look like the past six years – lost, drifting, and uninspiring.

At this point, “incremental moves” won’t cut it. Cherington will need to make drastic, franchise-altering decisions to show that the Pirates are actually moving forward. Here's what some of those decisions could actually look like.

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

Commit to a real core – or tear it down

Half-measures have killed Cherington’s tenure in Pittsburgh. In 2026, he must either go all-in and add proven MLB talent around Paul Skenes or pivot to a true rebuild by trading star players like Oneil Cruz or Bryan Reynolds for elite prospects. For Cherington, standing still is a death sentence.

Spend in free agency (for real this time)

The Pirates have avoided meaningful long-term free agent contracts under Cherington. That has to change. In 2026, he must bring in at least two established, middle-of-the-order bats – no more reclamation projects, and no more one-year "bridge guys."

Overhaul the hitting development program

Arguably the biggest indictment of Cherington is how many Pirates hitters stall out or collapse at the MLB level. He may need to fire key player development staff and bring in new hitting/pitching coordinators with track records of fixing swing-and-miss issues. Otherwise, the farm pipeline will keep producing replacement-level talent.

Fix the catcher situation

The Pirates’ revolving door at catcher has been a glaring weakness under Cherington, and Rafael Flores’ rushed promotion after the David Bednar trade exposed a lack of depth and planning. Cherington must either sign or trade for a proven MLB catcher, or draft and fast-track an elite catching prospect. Until the position is stabilized, the pitching staff (including Skenes) is handicapped.

Take accountability for prospect busts

While we're on the topic of catchers, 2020 first-overall pick Henry Davis is just one of the many of Cherington’s “big rebuild pieces” that have fizzled at the Major League level. In 2026, he needs to stop clinging to sunk costs. Moving on from players like Davis if they’re not producing sends the message that results matter, not draft pedigree.

Rebuild trust with fans and the clubhouse

Anonymous players calling the Pirates “a bad organization” is a PR disaster. Cherington must improve communication with players. be transparent about the direction of the team and reconnect with fans who are tuning out in record numbers. Extending manager Don Kelly was a solid step in the right direction here, but more needs to be done.

Push for Nutting to loosen the purse strings

This is the hardest, but also the most necessary. If Cherington can’t convince ownership to spend at least league-average payroll, he’ll never build a winner. His job security may hinge on proving he can win that internal battle, not just assemble prospects.