Can you imagine George Steinbrenner watching this current Yankees team — the once-mighty New York Yankees — go 15 years without a World Series title since his passing? The man who said, “Winning is the most important thing in my life, after breathing,” and led by it, would have hardly imagined a version as such. But here they are.

For the umpteenth time, the Yankees will be running it back after falling to the Blue Jays in the ALDS Game 4. And Aaron Judge, touted as the greatest right-handed hitter of modern times, is left to watch as his best years pass by without carrying a ring. Why is it so? Rich Eisen asked. Why is it that there have been no explosive moves or new outlooks? Simply put, it’s the top man, Hal Steinbrenner, banking on the positives in a way the Yankees faithful aren’t used to.

“You grew up with the Steinbrenner doctrine: if you don’t win the World Series, then your season is a failure. Well, the person who doesn’t believe in the Steinbrenner doctrine is Hal Steinbrenner. The son. He doesn’t operate that way,” ESPN’s Buster Olney answered on the Rich Eisen Show.

“He gives them credit for the fact that they haven’t had a losing season since 1992. He gives them credit for the fact that last year they played in the World Series, that this year they had the second-best record in the American League, in a way that Yankee fans don’t.”

George Steinbrenner built a club that tolerated nothing less than a World Series. He ensured they had the highest payroll in the league for 12 consecutive years and went through 11 different managers when they failed to secure a ring between 1979 and 1995. Steinbrenner Sr. was aggressive, but you couldn’t say the same for his son.

For eight seasons, Joe Girardi remained unreplaced despite winning no championships. It has been the same with Aaron Boone, who enters his ninth season in 2026, and GM Brian Cashman, who has now gone 24 years without a ring in his 25-year tenure.

Despite being the most valuable club in the league with an $8.2 billion estimation, the Yankees seem to have hesitated to spend big– Juan Soto was a good example. Sure, the younger Steinbrenner has ensured consistency, but what has that resulted in?

“I’m genuinely concerned that Aaron Judge’s talent is being ultimately wasted right now,” Eisen added.

His concern isn’t misplaced. Since 2017, he’s led the AL in home runs (when healthy) with a career OPS+ of 166 — elite territory with Trout and Betts. Yet the Yankees have reached the ALCS just once in that span, hitting under .220 in the postseason. Earlier this year, he also moved up to sixth on the Yankees’ all-time WAR leaderboard. Those above him have all secured a ring or two.

So if Hal Steinbrenner & Co. don’t help Judge with adequate support on the roster, not only will he walk around as the best Yankee without a ring, but the direction of the most storied club will be rewritten. However, not all is lost.

As Olney noted, the Yankees have been gradually adding versatility with the likes of Jazz Chisholm (hit 31 homers and stole 31 bases) and Cody Bellinger (29 homers and 98 RBIs). But a more crucial move is still to be made.

They have to figure out shortstop

Yankees shortstop Anthony Volpe has a batting line of .212/.272/.391 with an OPS of .663, with bad defense, and it’s his third consecutive season of below-average production in his first three seasons in the league. Volpe’s best season was last year’s .243/.293/..364, and you can’t win or even aspire for a championship with that kind of production in such an important place where Derek Jeter has played.

The  Yankees have an internal fix like last season’s trade deadline acquisition, Jose Caballero, who is also bad offensively but offers good defense.. Then? The upcoming winter free agency offers so many players, like Miguel Rojas (who has 4.5 WAR), Bo Bichette (28, 4.1), Ha-Seong Kim (30, 2.9), and others like Isiah Kiner-Falefa and Jorge Mateo. Rojas has the highest WAR among them, but given his 37 years of age. As Bo Bichette, who hit .311, has been entirely out of the lineup since September, Bichette is the best shortstop the winter free agency is offering.

And the team that made a big splash to keep Juan Soto last year and even expected to do the same for Kyle Tucker and Cody Bellinger this season can easily afford Bichette’s expected $27M AAV for the next season.

Plus, Detroit Tigers ace Tarik Skubal will be available in the coming winter. The Tigers might trade him, and who knows, adding Skubal would give the Yankees the best front-four starters in baseball. We know this “bully rotation” would cost a lot, but why not follow the same approach the current best team in baseball, the Los Angeles Dodgers, used last season to repeat as champions?