hal steinbrenner yankees
Jessica Alcheh | USA TODAY Sports

More often than not at ESNY, we’ve discussed Hal Steinbrenner’s positive qualities as owner of the Yankees. Because, in fairness, there are a few.

Unlike his father, the late great George, Hal doesn’t throw money at the glorified Band-Aids that are aging players. Not by default at least. Frustrating as longtime general manager Brian Cashman is, Hal actually lets him have a farm system instead of gutting it year in and year out.

Steinbrenner said there was no “absolute payroll number” when it came to re-signing Aaron Judge last offseason. Nine years, $340 million, and a phone call from Italy later, Judge is the captain of the team.

Steinbrenner, at least earlier in the season, was having monthly meetings with Judge and Gerrit Cole. Whatever’s said in these closed-door meetings, it’s clear the younger Steinbrenner clearly has some of his father in him.

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In which case, how come he hasn’t weighed in on this absolute disaster of a season? The Yankees are 55-52, last in the AL East and falling more and more behind in the Wild Card race daily. Judge is the only consistent performer in the lineup and missed two months with an injury. Nobody stepped up in his absence. At all.

Now, adding insult to injury, the Yankees just had their worst trade deadline under Cashman and Steinbrenner. Instead of adding a much-needed bat to MLB’s second-worst lineup, the Yankees added … relief pitcher Keynan Middleton and former top prospect-turned-bust Spencer Howard.

And where is Steinbrenner? Radio silent. Cashman delivers platitudes upon platitudes about how his last place team can still make a run deep into the postseason.

Meanwhile, the Yankees lost another series to the rival Rays on Tuesday night. Their only offense in the 5-2 loss came from a pair of two-out hits in the ninth inning.

Not for nothing, but The Boss never would have stood for this. It might not have been the right move, but he’d have been far more aggressive in the trade market. He’d have at least pushed a little bit harder to move Harrison Bader, Wandy Peralta or even Luis Severino’s expiring contracts. Moreover, the media would at least get an earful about how disappointing the season has been.

None of this is to say Steinbrenner is incapable of pulling a George and being firm when he needs to be. Judge would probably be a Giant or Padre otherwise.

The issue, rather, is that Steinbrenner sees the issue as a simple matter of players underperforming. He seems blind to the fact that his long-trusted GM, while certainly not bad at his job, is completely stuck in his ways. In the meantime, this entire season has been proof positive that Cashman’s model (and the “Yankee Way”, for that matter) is completely broken.

So what can Steinbrenner do? The answer isn’t firing his front office, his manager, or blowing up his team. That’s a conversation for another day.

But instead, he should just accept he needs to be more involved day-to-day. For all of father George’s fault, you could never say he didn’t care about building a winning team. Remember, the Yankees hitting rock bottom and then rebuilding in the early ’90s only came from Steinbrenner being banned from baseball. Had he not been, he easily would have made maneuvers to keep the Yankees competitive (in his own weird way).

This isn’t to say Hal becomes a de facto GM a la Astros chairman Jim Crane, but just does more than watch from afar in Tampa. Two weeks in New York and two weeks off is plenty. Even one week a month is acceptable.

All in all, Steinbrenner needs to recognize this is when he leaves his mark as owner of the New York Yankees. He’s at Yogi Berra’s infamous fork in the road and it’s time to take it.

Down one path is being proactive and making the hard decisions required of fixing a failed system’s foundation while also remaining a competitive player. It won’t be easy, but it’s doable.

Down the other, however, is sitting back and watching the house collapse until it’s too late.

Hard choices are coming for the Yankees. Let’s see if their beleaguered owner makes them.

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Josh Benjamin has been a staff writer at ESNY since 2018. He has had opinions about everything, especially the Yankees and Knicks. He co-hosts the “Bleacher Creatures” podcast and is always looking for new pieces of sports history to uncover, usually with a Yankee Tavern chicken parm sub in hand.