Can you imagine George Steinbrenner watching this current Yankees team — the once-mighty New York Yankees — go 16 years without a World Series title since his passing? The man who said, “Winning is the most important thing in my life, after breathing. Second place is the first loser,” would be fuming. After last year’s World Series loss to the Dodgers, the Yankees won 94 games — second-best in the AL — only to fall to the top-seeded Blue Jays in the ALDS Game 4.

Since that loss, with another season’s ending in the familiar way, everyone was searching for the main culprit. Most people blame manager Aaron Boone, while others point fingers at GM Brian Cashman, but a recent episode of The Rich Eisen Show gave us a huge hint where ESPN’s Buster Olney pointed to where the actual problem lies.

In the episode, Rich Eisen spoke for all Yankee fans and asked Olney, “On behalf of all Yankee fans… why do the Yankees keep running it back?” and why they just “tinker here, tinker there”  and even asked “What… why does that seem to be the modus operandi of, of Hal Steinbrenner, best you can tell?”  Eisen basically wanted to understand why the team avoids a “completely new way of looking at everything.”

The good thing was that Olney didn’t hide from answering it. “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,”

Hal Steinbrenner’s approach has always leaned toward sustainability over shock. Since taking over in 2010, he’s prioritized staying under luxury tax thresholds, focusing on analytics, player development, and long-term payroll flexibility, unlike his father, who often splurged on marquee free agents such as Reggie Jackson and Alex Rodriguez.

Olney explained on YouTube. “He gives them credit for the fact that they’ve made the…. they haven’t had a losing season since 1992… 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.”

Rich Eisen quickly pointed out the cost of this new philosophy. “I’m genuinely concerned that Aaron Judge’s talent is being ultimately wasted right now,” Eisen said. Eisen feels Judge is “surrounded by a lineup that doesn’t get on base for him enough.” He said the team is all hit-or-miss. He even agreed with analyst Buck Martinez. Martinez famously said the Yankees don’t win if they don’t hit home runs.

The judge’s 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 — proof the lineup keeps letting him down.

The good thing is that here, Buster Olney gave us some hope. Though glacially, ” They’re [the Yankees] changing..Okay. You remember the years, uh, three, four years ago, they constantly had those right-handed hitting lineups that you’re like, ‘That is not going to play in Yankee Stadium.’ Uh, and that was an all-or-nothing lineup. They’ve gradually, by adding Jazz Chisholm, last year they traded for Cody Bellinger, they have become a little bit more versatile, uh, a little bit more speed,” Olney pointed out.

This is true. Chisholm hit 31 homers and stole 31 bases, while Bellinger added 29 homers and 98 RBIs, but still, they have one problem remaining is

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?