A conversation with Hal Steinbrenner 

TAMPA, Fla. — Hal Steinbrenner heard the boos.

Each time.

The Yankees' managing general partner got it good from fans at the Stadium during separate on-field ceremonies in 2022, and the boos were loud and lasting. The first was Aug. 21 during Paul O’Neill’s jersey retirement celebration and the second came on Sept. 9 when Derek Jeter was honored for his induction into the Hall of Fame.

And not only did Steinbrenner hear the boos, they hurt.

“Of course,” he told Newsday in an interview last week. “Players don't want to be booed by their fans, so why should owners? Why would anybody?”

Steinbrenner, who said the reaction from the fans was more “hurtful” to members of his family than to him, said it was not unexpected.

“I know the passion of our fans. I understand it. It's part of the job,” he said. “They were certainly not happy that we did not get the Judge deal done [before the season]. Did it bother me? Of course . . . but I did expect it.”  

He added: “I understand the passion, and that's one of the things we all love about our fans is the passion. And that passion can manifest itself in numerous ways. Not always positive. But I understand.”

Steinbrenner again mentioned failing to bring Aaron Judge back into the fold before the 2022 regular season as feeding the fans’ reaction (Judge turned down the Yankees’ $213.5 million extension offer, then embarked on the greatest walk year any player has ever had, turning an American League-record 62 home runs and an MVP season into the nine-year, $360 million free-agent deal that kept him in the Bronx).

Still, at some level, Steinbrenner, 53, seemed to understand the booing ran deeper than the failure to sign Judge in March 2022.

Fairly or not, Steinbrenner is perceived by much of the fan base as a distant presence overseeing a franchise that is estimated to be worth well above $6 billion, someone whose passion to win the World Series doesn’t match that of the fans. They see him as someone unwilling to spend big on every shiny free-agent object that presents itself in a given offseason and, ultimately, an owner — even with a payroll this season that could approach the $300 million mark by season’s end — all too accepting of not having qualified for a Series, let alone won one, since 2009.  

In short, he isn’t his father, George,  a larger-than-life figure while alive who has taken on an almost mythical status among fans since his death in July 2010.

Much of the myth comes from the success The Boss experienced toward the end of his tenure as owner — five World Series titles between 1996-2009, including three straight championships from 1998-2000. The many, many years of overall franchise dysfunction, suspensions of Steinbrenner  and playoff-less seasons have been mostly forgotten.

“There were many times when the fans were not happy with him,” Hal Steinbrenner said, mentioning the firing of Yogi Berra 16 games into the 1985 season after a guarantee two months earlier that the legendary Yankee would get the entire season no matter what. “There were just a lot of things. But I know I can speak for my sisters [Jennifer and Jessica], we're glad it is the way it is. That's how we as children want him to be remembered. Not all the booing and all the negative publicity and rash decisions that created it. So I’m good with it.”

A popular phrase among longtime club employees whenever just about anything happens, good or bad, is “What would George do?”

It is a question asked frequently by fans.

Hal Steinbrenner asks it occasionally, too.

So what would George have done when it came to Judge and his free agency in the offseason?

Well, it’s hard to imagine The Boss letting a player like Judge go  under any circumstances — certainly not one who has attained a popularity approaching a Jeter-ian level and, as George Steinbrenner would say, one of those rare players who “puts [butts] in the seats.”

And the possibility of losing Judge was exactly the nightmare scenario Hal Steinbrenner faced as December’s winter meetings began.

The Giants, the team Judge grew up rooting for in Linden, California — which is about two hours from San Francisco —  were serious suitors. As were the Padres, who came late to the table but with bundles of cash.   

There was a report early in the meetings that Judge was choosing the Giants, which caused shockwaves throughout the game  — shockwaves that made their way to Milan, Italy, where Steinbrenner was vacationing.

Though Steinbrenner quickly found out the report was inaccurate, he admitted that the thought of ''oh-expletive-we’ve-lost-him'' went through his mind.

“It was very concerning,” Steinbrenner said. “Not a good feeling.”

Steinbrenner multiple times has told the story of his conversation with Judge from Milan at 3 a.m. (Judge’s time in California) in which he and the outfielder essentially worked out the deal.  

But there had been a first conversation the night before, one in which Steinbrenner, who is shy by nature and often refers to himself as “an introvert,” felt he didn’t do a good enough job of getting Judge to completely “verbalize his feelings” regarding staying.

For that reason, he sent a request via text for a second phone call, which occurred a night later.

“I just wasn't getting exactly what I wanted,” Steinbrenner said. “[The second conversation], I just said, ‘Look, you've talked to your wife, parents, family . . . what is important to you? What is important to them? Talk to me.’ ”

Central to it was Judge, who will turn 31 on April 26 and believes he can play well into his 40s, wanting a ninth year.

That wish was granted, and general manager Brian Cashman soon was calling Steinbrenner “the Mariano Rivera” of the Judge negotiations.

The money and the years carried the day, as they usually do in these cases, but from Judge’s perspective, there also was a personal element.

“One thing we talked about was about trying to build a relationship,” Judge said in an interview Saturday. “Because I wanted to be a voice that’s in this clubhouse and I could go to him and say, ‘Hey, the players are talking about this. I want to go straight to you and kind of give you the heartbeat of what’s going on down here.’ ”

Judge continued: “Our relationship’s been great so far. We really didn’t have much of a relationship before, but that was one of the things I wanted to say is like, ‘Hey, I’m going to be here for the next nine-plus years and I want to build a relationship where we can communicate openly and freely, things on my mind, things on your mind.’ And he’s been all about that.”

Steinbrenner said of his relationship with Judge: “I’m an introvert, so getting to know somebody is not the easiest thing for me. I probably haven't been as good at it with a lot of the players through the 14 years as I should have.”

But Steinbrenner, whom fans might be surprised to hear Judge refer to as “a jokester,” has been a more frequent presence in the clubhouse, though not too often and never when the media is inside.

The owner took note when one veteran player recently questioned why recent franchise luminaries such as Jeter, Jorge Posada and Mariano Rivera are hardly around.

Jeter, the 15th captain in club history and the last player with the title before Judge was named No. 16 in December, is of particular interest to fans, and Steinbrenner said to stay tuned.

“I’m not going to get into what we’ve talked to him about, but we’ve certainly reached out to him about one or two things,” Steinbrenner said.

Of Jeter, who still could end up doing some things for the YES Network, having an actual organizational role, Steinbrenner said: “That’s what I would talk to him about. He would probably have better ideas than I as to what he would be willing and wanting to do.”

Steinbrenner officially took the reins of the Yankees in November 2008 and is far more comfortable in the job than he was at the start. He said there are a variety of aspects of it that he knows now that he didn’t know then — labor, for example, as Steinbrenner sits on MLB’s labor policy committee — but growing up around his father as he did, there was plenty he understood from Day 1.   

“When it comes to things like the fans and their expectations and how New York’s a tough place to run a business,” Steinbrenner said, “that was obviously not a surprise.”