George Steinbrenner and the Art of Teshuvah


steinbrennerBy CJ Srullowitz

The news last week that George Steinbrenner, principal owner of the New York Yankees, had died unleashed a spectrum of commentary, ranging from the begrudgingly positive to the excessively fawning. For the average baseball fan growing up in the 1970s and 1980s, familiar with the constant turmoil that surrounded the Boss and his beloved Bronx Bombers, the rehabilitation of Steinbrenner’s legacy is nothing short of miraculous.

It’s a miracle that he himself put together.

This is really the tale of two Steinbrenners. The first came along in 1973, when he led a group of investors to buy the Yankees for ten million dollars. The Steinbrenner of the early days was crass, callous, and cruel. The Yankees quickly improved and won two World Championships before the end of the decade. Whether they won because of or in spite of their owner’s behavior is debatable. It’s also beside the point.

George Steinbrenner excused his conduct as necessary in order to win. He put winning ahead of everything else. Winning was the ends that justified the means-and the meanness. “I sign the paychecks,” was his reasoning for treating employees as nothing more than disposable puppets in the grandiloquent theater that was Yankees Baseball. Sixteen games into the 1985 season, he fired the Yankees greatest living legend, Yogi Berra, after publicly promising him a full season to lead the team. And he didn’t even have the courtesy to tell him himself; the deed was done through another executive. Berra was humiliated and stayed away from the Yankees for over a decade.

He famously fired a stadium electrician for a malfunctioning loudspeaker, and a secretary for ordering the wrong sandwiches. “You live up to his impossibly perfect image of the New York Yankees or Steinbrenner would exact retribution,” wrote Joe Posnanski wrote in Sports Illustrated.

Harvey Greene, a former Yankees PR director, said, “The phone would ring in the middle of the night and you knew it was either Mr. Steinbrenner or a death in the family. After a while you started to root for a death in the family.”

Steinbrenner’s antics were tolerated for another decade until he finally crossed the line in 1990-paying $40,000 to a degenerate gambler to spy on his All-Star outfielder, Dave Winfield-and was
banned from the game in by then-commissioner, Fay Vincent.

But it turns out that there was another side to George Steinbrenner that was not as well known.

Just ask Ken Waldrep, who, in 1974, while playing football for TCU against Alabama, was hit on a play and became paralyzed. Steinbrenner was watching the game from the stands. He helped pay Waldrep’s medical bills and for a specially equipped van. He also kept up with him, lending moral, in addition to financial, support.

Ask Eddie Robinson, the famous football coach of Grambling University. When Robinson’s Urban League Classic football game, which raised funds for nearly 500 scholarships, was straining financially, Steinbrenner loaned them Yankee Stadium to host the event.

Ask Fay Vincent, the aforementioned baseball commissioner who banned Steinbrenner from the game. Vincent recalled the first conversation he ever had with Steinbrenner. Steinbrenner phoned Vincent, asking to “help him raise money for a former football coach at Williams College (which we both attended) who was ill in Florida with Alzheimer’s and needed full-time nursing. George and I shared enormous affection for this coach, and for years we and several others helped him and his wife in their old age.”

Ask Lorraine Blakely, who was almost killed, at age seven, in a freak accident that left her with a crushed skull. Steinbrenner wrote a check to cover the brain surgery of this young girl, after he learned from a newspaper that her father was between jobs and the doctor refused to operate until he was paid.

One former employee reminisced about the time his mother came to New York for a visit, and how Steinbrenner treated her like a queen during her stay. But his behavior toward the employee himself, remained cold. Lou Piniella, the former Yankees player and manager, summed it up: “George is a great guy, unless you have to work for him.”

But by the time Commissioner Bud Selig reinstated him in 1993, a new George Steinbrenner began to appear. By that point, the team (through general manager Gene Michael) had done much to rebuild its depleted minor league system-a system Steinbrenner had helped to deplete by trading away future talent for aging stars. As such, Steinbrenner became the greatest beneficiary of his own exile. Think Jeter, Posada, Pettite and Rivera.

Steinbrenner was still tough on his employees but the cruelty, for the most part, was gone.

Fast forward to 1999, a humbled Steinbrenner arrives at the Berra Museum and Learning Center in New Jersey to make amends. “You’re fifteen minutes late,” Yogi quipped, as Steinbrenner approached.

“Yogi, I’m afraid I’m fourteen years late,” Steinbrenner tearfully responded.

This split personality, which George Steinbrenner finally corrected late in life, is common to many of us. Too often, we can be very kind to guests, but not so nice to our own families. We can be the most charming people in shul, but too tough on our own children. We can smile at strangers but snap at our spouses.

On a national level, too, we are guilty of this dichotomy. Rav Berel Wein, shlit”a, often spoke of people who “love Judaism but hate Jews.” We criticize members of Klal Yisrael who don’t measure up to our standards. We may even belittle others for taking a different path toward Avodas Hashem.

And we tell ourselves that we do this for constructive purposes. It’s love of our families that make us so hard on them. It’s our love of Torah and Yiddishkeit that makes us so critical of others. The end justifies the means. Like George Steinbrenner, we just want to win.

Aharon Hakohein, whose yahrtzeit just passed on Rosh Chodesh Av, was known as the “oheiv shalom verodeif shalom-lover of peace and pursuer of peace.” Aharon pursued shalom relentlessly. As we get closer to Tisha B’av, the anniversary of the destruction of the Bais Hamikdash because of sinas chinam, we are reminded to take a page from Aharon Hakohein’s playbook and not simply look for opportunities of ahavas Yisrael, but to pursue them.

We, like Mr. Steinbrenner, already have it inside of us. We just have to shift a little bit, like a batter adjusting his hitting stance, and let it out.

CJ Srullowitz, longtime baseball fan and a financial advisor in New York City, blogs at

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  1. Another story I heard was that a jewish boy was afraid to go to a certain college (were steinbrenners son went to) because of anti-semitism. The next day he got a call from george telling him to go and not to worry about anti- semitism and said he will prevent that from happening.

  2. Yes we all know someone like that. My Zeideh was like that. Maybe it was a generational thing. They were all hard on family and nice to strangers. This drove me away from him sadly. In the end, the writer’s advice is correct. We need to pursue Shalom and increase our midda of Ahavas Yisrael. Amen.

  3. there are so many tzadikim and ehrliche yidden to learn lessons from why do people always try to learn from celebrities?