The Yankees’ 17-Year Title Drought Is on Hal Steinbrenner

The lionization and romanticizing of the late George Steinbrenner can get a little out of control whenever his beloved New York Yankees fail to meet the standards he begin setting half a century ago.

The Yankees won seven World Series under Steinbrenner from 1977 through 2009 — the second-most championships for a team in one of the four major North American pro sports leagues in that span behind only the NBA’s Los Angeles Lakers (nine).

But Steinbrenner was also a bully who made a ton of mistakes with his form of impulsive, hands-on and sometimes even illegal leadership, as evidenced by the Yankees going without a championship from 1979 through 1995, a span in which he changed managers 16 times and general managers 12 times.

Yet there’s got to be something between Steinbrenner’s worst impulses and this — a second 17-year title drought, which the Yankees officially “achieved” Wednesday night when they were swept out of the American League Division Series with a 4-3 loss to the Tampa Bay Rays.

With each passing year, those of us old enough to remember George’s manic run wonder how he’d respond to the latest elimination — and each year, Hal Steinbrenner, George’s younger son, responds by basically running it back with the AL’s bridesmaids.

Brian Cashman has been the general manager since 1998 while Aaron Boone, who closed out his ninth season as manager last night, is the only manager hired under Hal.

In many ways, Hal Steinbrenner’s placidity is admirable. He does not buy up every big-name free agent like his Dad did, but he spent just north of $300 million on this year’s team. Every one should want to work for a lower-case boss who provides resources and gets out of the way.

And the Yankees are always right there, even if right there is always second place. They have been eliminated by one-year wonders (the 2018 and 2021 Boston Red Sox and the 2025 Toronto Blue Jays), by teams in the midst of a mini-renaissance (the 2010 Texas Rangers, the 2011-12 Detroit Tigers and the 2020 Rays), by the AL’s unquestioned super power (the Houston Astros in 2015, 2017, 2019 and 2022) and even once in the World Series by the Los Angeles Dodgers in 2024.

But at some point, isn’t life on this treadmill unacceptable — especially since the defensive debacle in the series-turning 5-2 loss in Monday night’s Game 2 was basically a sequel to Game 5 of the 2024 World Series, when the Dodgers clinched the title by overcoming a five-run deficit with the help of three Yankees errors as well as Gerrit Cole failing to cover first base on a routine grounder during the fateful fifth-inning rally?

Why are the Yankees always doing the same thing — fielding a top-heavy, fundamentally unsound team — and expecting a different result?

How can the Yankees expect a different result?

The easiest target for armchair owners is going to be Boone, who has never struck anyone as the second coming of Joe Torre, Miller Huggins or even Buck Showalter.

Boone’s first-guessed decision to bat Trent Grisham — who hit .211 this season and was 2-for-10 in the playoffs entering Wednesday night — atop the lineup for Game 3 promptly haunted him when Grisham made the final out of the season as Ben Rice, the Yankees’ best hitter this season, stood on deck.

But George Steinbrenner would have admired the toll the loss took on Boone. It took Boone 28 minutes after the last out to reach the podium in the bowels of Yankee Stadium, where he used the phrase “it’s the worst” three times to describe how elimination feels.

Following his nearly 16-minute press conference, Boone, still wearing his uniform, wandered around the periphery of the Yankees locker room, sitting down briefly to talk to pitchers Cam Schlittler and Carlos Rodon.

Plus, this is baseball in 2026. With the exception of the Milwaukee Brewers’ Pat Murphy, managers are just human shields for the front office decision makers. And no decision-maker is more entrenched than Cashman, who has somehow consolidated power over the last three decades to the point where it is beginning to feel like he is GM for life.

If the Yankees are annually fielding a top-heavy, fundamentally unsound team, it’s because that’s what Cashman has built. Never has this been more obvious than in the absence of Aaron Judge, whom Boone described late Wednesday night as “the greatest player in the world.”

In regular season play since 2018, the Yankees are 424-290 when Judge plays and 173-154 when he doesn’t. Judge missed the playoffs with a calf strain, so he watched with the rest of us as players not named Ben Rice went 9-for-82 with no homers, two RBIs and five walks against the Rays.

“Every year is different,” Boone said when asked why the Yankees keep coming up short.

Except it’s not, and it’s about time Hal Steinbrenner took a page from his Dad’s book and asked Cashman why.