It’s been said many times over a century: earning your pinstripes with the New York Yankees is one of the hardest things to do in baseball.
Just take Anthony Volpe’s rollercoaster career with the ballclub, which has once again become a storyline as they head toward the postseason. Through four seasons, Volpe, a former first-round pick by the Yankees, has been showered with cheers, vitriol and everything in between from the fan base whose expectations will never fall lower than World Series or bust.
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If that’s not hard for a 25-year-old to deal with, Hall of Fame left-hander CC Sabathia was even a bit intimidated by the weight the pinstripes hold when he was a free agent in 2009. He eventually signed on and became a beloved figure in Yankees lore — his No. 52 is set to be retired on Sept. 26 — but he understands it’s not for everybody.
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Anthony Volpe of the New York Yankees looks on after the fifth inning against the Colorado Rockies at Yankee Stadium on Sept. 10, 2026, in New York City. (Getty Images)
While speaking at his PitCCh In Foundation’s 6th Annual Golf Classic at Alpine Country Club on Monday, Sabathia suggested to OutKick that the Yankees should come up with a way to not coddle those young players from the expectations, but rather help ease their way into it.
“It’s hard to watch, right?” he said when asked about what Volpe has gone through, especially now that he’s hearing cheers again after performing well following his latest call-up. “Because he’s from here, he wants to do well. And I just watched so many young players for the Yankees, whether it’s Gary Sanchez, whether it was Miguel Andujar, whoever it is, you get a label and that’s what it is, which sucks especially for a young player. I feel like the only young player that came in and did well was [Aaron] Judge because he hit 50 homers and everybody was off his back. So, it’s hard to build up equity with the fan base when you’re so young.
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“George Lombard [Jr.] just went through the same thing. He had six errors in a row, and you started hearing grumblings and all these different things. So, it’s hard to develop here as a young player and I think the Yankees need to do a better job to insulating these guys and helping them understand what it is to put on the pinstripes. There’s going to be ups and downs, you gotta cancel out the noise and go out and play baseball every single day.”
Of course, it’s easier said than done in a New York market where championships, no matter the sport, are expected each time a season begins. But the only way through is forward for players like Volpe, whose ups and downs since reaching the big leagues have kept fans guessing. They see what could be, but consistency hasn’t been there for the highly touted prospect.
CC Sabathia speaks at his PitCCh In Foundation’s 6th Annual Golf Classic on Monday, Sept. 14, 2026 at Alpine Country Club in New Jersey. (Cesar Nunez)
“You think about Volpe’s perseverance and determination — what else is he going to do? He’s not going to quit,” Sabathia added. “This is what he wanted to do his whole life. He wanted to play baseball his whole life, and he’s been in tough situations. Baseball is a hard game, but I think he’ll be better for sure, whether he’s playing second base, whether he’s playing shortstop in the Bronx or somewhere else.
“Wherever it is, he’s talented enough to play the game. Hopefully he can do some things well and help us down the stretch. Jazz can get healthy, they can platoon. We’ll see what happens. But I’m super excited for his future, not only here but if it’s somewhere else, too.”
Sabathia spent 19 years in the major leagues, where expectation was immediate for him as well coming up with the Cleveland Indians in 2001 as a 20-year-old. He felt that pressure there, and even for the half season he played with the Milwaukee Brewers.
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But arriving in New York was a different story in 2009. Sabathia and the rest of his star teammates came through, though, winning the World Series that season and giving a franchise synonymous with titles its 27th to extend the MLB record.
Since then, the Yankees haven’t been able to add their 28th, making just one Fall Classic in 2024 before falling to the Los Angeles Dodgers. Sabathia hopes this could be the year the Yankees get back and see it all the way through so his squad isn’t still the last New York team to win it all.
But then again, the pressure is immense to make that happen. It’s already begun as the Yankees clinch yet another postseason berth and the chance to hoist the trophy at the end of the season.
It’s pressure Sabathia feels is found nowhere else in MLB, especially for young players trying to make a name for themselves on one of the most iconic sports franchises in the world.
Anthony Volpe of the New York Yankees is in action against the New York Mets at Yankee Stadium on Sept. 12, 2026. The Mets defeated the Yankees 12-2. (Getty Images)
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“This is the only place it happens. If you think about anywhere else, it doesn’t happen anywhere else. You think about what Roman Anthony is going through in Boston. If that was here in New York, it would be leading Sportscenter every single day,” Sabathia said.
“It’s a different beast when you put on the pinstripes.”
