Yankees' Aaron Judge Running Out of Time for Ultimate Goal

Aaron Judge will be 34 for the 2026 season, and while he has made history for his excellence with the New York Yankees time and time again, he may be joining an unfortunate list of greats by the time he retires.

Though he shows no signs of slowing down, Judge still has not secured a World Series win in his ten seasons in New York (his entire MLB career), despite a list of feats landing him among the all-time greatest to play the sport.

Judge was recently compared to some of those names by MLB journalist Mike Lupica, who noted that Judge has time, but not infinite time.

"[...] here is a list from which Judge wants his name removed as soon as possible, maybe even as soon as next season, when he turns 34: The one with the greatest baseball players who never played on a World Series winner," Lupica wrote.

"That is the one with Ted Williams’ name on it, and Ken Griffey Jr., and Ernie Banks, and Barry Bonds; other Hall of Famers like Tony Gwynn and Rod Carew and Ichiro Suzuki and Harmon Killebrew. If you want to go back further, Ty Cobb never won a World Series, either. Mike Trout might never win one with the way his injury-filled career is playing out."

Judge is Ahead of At Least One Legend Already

May 30, 2007; Toronto, ON, Canada; New York Yankees bench coach (23) Don Mattingly and hitting coach (54) Kevin Long smile after beating the Toronto Blue Jays 10-5 at the Rogers Centre in Toronto, ON. Mandatory Credit: Tom Szczerbowski-Imagn Images | Tom Szczerbowski-Imagn Images

Lupica did note that Judge is already one step closer in his playing career than Yankees legend Don Mattingly ever got — that is to say, he has played in a World Series (in 2024, against the Los Angeles Dodgers). Mattingly made his first-ever World Series just this year, as the Toronto Blue Jays' bench coach in 2025. The Blue Jays, of course, fell short, leaving Mattingly without a championship once again.

Judge is obviously feeling this drought himself, and has shared that he would trade all of his accomplishments to date for another opportunity at a World Series championship.

“I'd trade every award I've gotten and every All-Star appearance for an opportunity to win a championship," Judge recently said, per Gary Phillips of the New York Daily News.

For his performance in 2025, Judge was the MLB batting champion, was voted AL MVP for the third time, won his fifth Silver Slugger Award, won his third AL Hank Aaron Award and earned his seventh All-Star appearance. He led the league in all batting slash line statistics, with a .331 batting average, a .457 on-base percentage and a .688 slugging percentage. He will give another year his all in 2026 and hope to avoid landing on the wrong side of history.

Make sure to bookmark Yankees On SI to get all your daily New York Yankees news, interviews, breakdowns and more!