Pirates fans fear Andrew McCutchen’s legacy is about to get messy beyond repair

For nearly two decades, Andrew McCutchen’s story in Pittsburgh has been a rare thing in modern sports: clean, linear, romantic.

Cutch was drafted by the Pirates. Developed by the Pirates. Elevated the Pirates. Became the face of a franchise that had forgotten what relevance felt like. Won an MVP. Ended a 20-year playoff drought. Came back home. Finished where it all began.

It was supposed to be simple.

Instead, Pirates fans are watching something they never imagined unfold — the slow, public unraveling of a relationship that once felt sacred. Not dramatic. Not explosive. Just… awkward. Cold. Lingering. And maybe irreversible.

McCutchen didn’t miss PiratesFest this weekend because he wanted to make a statement. He missed it because he’s not under contract. But in Pittsburgh, that absence felt symbolic. The face of a generation wasn’t there to shake hands, sign autographs, hug fans who’ve aged alongside him. And when general manager Ben Cherington was asked whether McCutchen would be back in 2026, the answer wasn’t warm. It wasn’t reassuring. It was corporate.

“We’ll see.”

That’s the kind of answer you give about a bench bat. Not about the most important Pirate of the last 20 years.

McCutchen heard it. And late Saturday night, he responded not as a brand ambassador or alumni figure, but as a man who feels discarded. He didn’t talk about WAR or roster construction. He talked about kids. About Roberto Clemente. About fans who deserved one last chance to say goodbye. He compared himself to Adam Wainwright, Albert Pujols, Yadier Molina, Clayton Kershaw, Miguel Cabrera — icons who were allowed to close their careers on their own terms.

What he was really saying was simple: Why am I different? And that question cuts deeper than any batting line.

Andrew McCutchen asks for closure while Pirates appear to have moved on without him

The Pirates will never say they’re moving on. They can’t. McCutchen’s place in this city is too sacred. So instead, they’ve let their actions speak. They pursued Kyle Schwarber. They signed Ryan O’Hearn. They acquired Brandon Lowe and talked openly about him getting DH at-bats. They added outfield depth in Jake Mangum and Jhostynxon Garcia. They rebuilt the very roles McCutchen occupied.

The Pirates didn’t replace McCutchen with hope. They replaced him with intention. They're acting like a team that has already planned its life without him, and that’s where the fear sets in for fans.

Legacies don’t only live in highlight reels. They live in endings. They live in how a story closes. Pittsburgh thought it was getting a final chapter that felt like a hug — one last season, one last ovation, one last lap around PNC Park. Instead, it’s getting silence.

McCutchen is still training. Still believing. Still asking for a chance. The Pirates, meanwhile, are leaving the door cracked just enough to avoid saying no, while clearly walking in the other direction. That limbo is what’s making this messy.

If McCutchen retires without playing another game in black and gold, it won’t erase what he meant to the Pirates and the city of Pittsburgh. But it will leave a scar on how it ended. Fans won’t remember 2013 without also remembering 2026. They won’t think of the MVP season without also thinking of the offseason he waited by the phone.

This isn’t about whether a 39-year-old is worth a roster spot. It’s about whether a franchise understands what it owes the people who carried it. McCutchen isn’t asking for charity. He’s asking for dignity. For closure. For the chance to walk off the field in front of the people who grew up with him.

Pirates fans aren’t afraid that McCutchen’s legacy will fade. They’re afraid it’s about to end in a way that doesn’t feel like McCutchen at all.