Andrew McCutchen keeps climbing the charts in Pittsburgh. He still can’t shake what might have been

The pain still lingers for Andrew McCutchen, even now in the final stages of a comeback season few saw coming.
So while the 37-year-old designated hitter appreciates the milestones he keeps checking off — like reaching 20 home runs in a Pittsburgh Pirates uniform for the eighth time during Tuesday night’s 6-4 win over Miami — the thoughts still linger about what might have been.
The truth is, he never wanted to leave. He became a victim of baseball economics in January 2018 when the Pirates traded their franchsie cornerstone to San Francisco, starting McCutchen on a five-year odyssey in which he bounced from the Giants to the New York Yankees to Philadelphia to Milwaukee.
Nice places, all. Good teammates. Some good times. But not Pittsburgh. Not his adopted home.
And so while McCutchen understands he is reaching rarified air on a team that’s been in the National League since 1887 — only Hall of Famer Willie Stargell has more 20 homer seasons with the Pirates than McCutchen — he can’t help but think about how much higher he’d be on some of the club’s all-time lists if not for that nomadic half-decade when he felt at times like a mercenary.
“It’s nice to be able to be with those guys and those greats, it’s amazing,” McCutchen said. “But it would be cool if I was here my whole career and then see where I would be at.”
Only, that didn’t happen. And as much as he has leaned into the warm embrace that accompanied his somewhat surprising return in early 2023, there’s a small part of him that is frustrated he had to leave in the first place.
“Every time I hear (where I rank), I’m like ‘Dang man, if only,'” McCutchen said. “I just go ‘cool’ and then I just move on.”
He admits legs that carried him to five All-Star appearances, the 2013 NL MVP and a Gold Glove don’t move quite like they used to. A partially torn left Achilles last September forced him to spend a portion of the offseason in a protective boot. Spring training was a slog. He felt like he was playing catchup, admitting “I just wasn’t there” and only too aware of doubters.
That made the 403-foot shot to the left-field seats off Miami’s Adam Oller with two on in the fifth — the 319th homer of McCutchen’s 16-year career — all the sweeter.
“Would a lot of people think I’d have (reached 20 homers)? Probably not,” he said. “It’s why I don’t look at them … because I know I can do it.”
McCutchen has morphed from dreadlocked, swagged-out blur to elder statesman. The gap between his age and 22-year-old Pirates rookie ace Paul Skenes is just one year less than the gap between Skenes and McCutchen’s 6-year-old son Steel.
Yet with all those years comes wisdom. Asked if he thinks he’s a sharper hitter now than he when he led the Pirates to three straight playoff appearances from 2013-15, he laughs and points out he’s become a cliche of sorts. The whole “if I knew then what I know now” thing.
Then, growing a little more serious, he sounded very much like a player who believes there is still plenty left to do in the game before walking away.
“I’ve definitely gotten better over the past five, six, seven, eight – I don’t know how many years it’s been – but I’ve gotten better,” he said. “And I’ve gotten myself back to where I feel like I can be.”
And while his batting average (.241) isn’t what it was a decade ago — the wear and tear on his body that comes from 2,116 games has seen to that — his eye remains elite.
What impressed Pirates manager Derek Shelton as much as McCutchen’s power surge — his 20 homers this season are the most he’s hit since 2021 — was the full-count curveball he let go by for ball four in his next at bat.
“Nobody takes that pitch,” Shelton said.
McCutchen still does. The walk was the team-high 53rd this season, his approach in the batter’s box an example of what being a professional hitter means to a team whose lackluster offense led to a second-half swoon that dropped them out of postseason contention.
The optimism that accompanied Skenes’ arrival in mid-May has turned into the reality that the young Pirates core isn’t quite ready. McCutchen, whose charisma and talent authored the last Pittsburgh baseball renaissance a decade ago, believes another one is on the way. And he very much wants to be a part of it.
While he will technically can become a free agent after the season and he wants to play “if I don’t embarrass myself,” the Florida native wants very much to do it in the place he never wants to leave again.
“I haven’t been in the playoffs in a while here and it would be nice to do it here,” McCutchen said. “We’re a special group of guys. We’re a special team. It’s there.”
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