For the past three offseasons, the Pittsburgh Pirates’ winter plans have ended with a familiar, feel-good move: Andrew McCutchen coming back home. It became something of a tradition - a reassuring constant in a franchise that’s spent more time rebuilding than contending.
McCutchen wasn’t just a roster addition; he was a symbol. A living link to the last time Pirates baseball truly mattered.
But this winter? Things feel different.
For the first time since this reunion began, McCutchen’s return isn’t a foregone conclusion. It’s not about sentiment anymore - it’s about fit.
And right now, the fit is murky.
The Pirates’ 2026 roster is starting to look like a team with real direction. Ryan O’Hearn is in the fold.
Brandon Lowe is, too. Bryan Reynolds is still locked into one of the corner outfield spots.
Suddenly, this lineup has depth, structure, and - most importantly - competition. It’s no longer about filling holes.
It’s about maximizing value. And that raises a tough question: where does McCutchen slot in?
A few years ago, even asking that would’ve felt like blasphemy. This is the Andrew McCutchen - 2013 NL MVP, the face of the franchise revival, the player who brought life back to PNC Park.
You don’t question his place. You just make room.
But baseball doesn’t run on nostalgia. Not for long.
The reality is, McCutchen isn’t an everyday outfielder anymore. The legs aren’t what they were, and nearly 20 years of big-league wear and tear have taken their toll.
That leaves designated hitter as the most logical role - but even that spot is crowded now. O’Hearn and Lowe both figure to get regular reps at DH.
Reynolds could rotate in when he needs a day off his feet. There are younger bats in the pipeline who might need those at-bats, too.
This isn’t about whether McCutchen can still contribute - he absolutely can. He still brings a veteran presence, a disciplined bat, and a clubhouse voice that resonates.
But the Pirates are finally building a roster with winning in mind, not just vibes. And that means every spot has to serve a purpose - not just carry a legacy.
For years, bringing McCutchen back made perfect sense. The team wasn’t ready to compete.
The roster lacked depth. He was a bridge - between eras, between fans and the front office, between what the Pirates were and what they hoped to become.
But bridges aren’t meant to be permanent fixtures. They’re built to get you from one place to another.
Now, Pittsburgh is trying to cross into something new. From “maybe next year” to “why not this year?”
And that kind of leap demands hard decisions. It means prioritizing role over resume.
It means every at-bat has to count toward the future, not just honor the past.
That doesn’t take anything away from what McCutchen means to this city or this franchise. Nothing ever could.
He’s a Pittsburgh icon, full stop. But if he’s going to be part of the 2026 Pirates, it has to be because there’s a clear, defined role for him - not just because it feels strange to imagine a season without him in black and gold.
This is the hardest part of growing up as a team - knowing when to let go. And for the first time in this heartfelt reunion, the Pirates may be standing at that crossroads.
It doesn’t mean the story is over. But if this chapter is closing, it’s because the team is finally ready to write a new one.