Judaism, Jails and Justice: A Conversation With Judge Jack B. Weinstein

Judge Jack B. Weinstein of the U.S. District Court for the Eastern District of New York talks about his encounters with the Rebbe—Rabbi Menachem M. Schneerson, of righteous memory; his long relationship with the Aleph Institute; and why at age 98 he still feels that there's more to accomplish. (Photo: Moshe Finkelstein/Chabad.org)

The 98-year-old federal jurist speaks about criminal justice, the Aleph Institute, and the Rebbe’s influence on his life and work

By: Dovid Margolin

On a rainy afternoon this summer, Judge Jack B. Weinstein called a recess on the case he was presiding over at the federal courthouse in Brooklyn, N. Y., to meet with an old friend and comrade-in-arms, Rabbi Sholom Lipskar.

Weinstein and Rabbi Sholom Lipskar, founder of the Aleph Institute, the leading Jewish organization caring for the incarcerated and their families, share a laugh in Weinstein’s chambers at the federal courthouse in Brooklyn in June of 2019. (Photo: Moshe Finkelstein/Chabad.org)

The two have known each other since 1981, when Lipskar, spurred on by the Rebbe, Rabbi Menachem M. Schneerson, of righteous memory, founded the Chabad-Lubavitch-affiliated Aleph Institute, the leading Jewish organization caring for the incarcerated and their families. Back then, Lipskar made a cold call to set up a meeting with Weinstein—chief judge of the U.S. District Court for the Eastern District of New York—already then known, in the 1982 words of the National Law Journal, as a “living legend.” The rabbi and the judge hit it off, and Weinstein, moved by the vision and wisdom of the Rebbe’s teachings on criminal justice reform and Lipskar’s passion, became a foundational supporter of Aleph’s work.

Today at age 98, Weinstein is by far the longest-serving active federal judge, having been appointed to the bench in 1967 by President Lyndon B. Johnson. In the half-century plus since, Weinstein has become known for his vast scholarship, talent and imagination, and, above all, his humanity. These attributes and his famously boundless energy have for decades placed him at the forefront of the battle for criminal justice reform in the United States.

Weinstein has time and again used his position to highlight policies he has called “unnecessarily cruel” to both defendants and their families. He has made his fair share of headlines along the way, including sparking a national furor in 1993 when, not long after taking senior status, he publicly announced at an Aleph conference that he would no longer hear drug cases due to overly harsh mandatory minimum sentences. Weinstein has also made waves for pointing out the wasted human potential of men and women incarcerated for crimes that garner little public sympathy, even those convicted of violent crimes. Calling it “the third-rail of the criminal-justice system,” a 2017 New York Times profile of Weinstein cited his striking denouncement of the “‘lack of sentencing alternatives’ for young violent criminals who are often written off … as ‘society’s unredeemables.’”

While the issues Weinstein and his fellow judges must grapple with are often complex—Weinstein has called sentencing “the most excruciatingly difficult task” a trial judge faces—there is a simple yet profound idea that sits at the heart of his worldview: He sees the men and women who come before him not as criminals, but as individuals who have made mistakes, human beings animated by a spark of G d.

“The other day, I had a man say, ‘I know I’m no good, Judge,’” Weinstein tells Lipskar as they sit in his chambers. “I said, ‘Did you ever hear me say that? Did you ever hear me say that? You are good, you are a person and you’re going to be helped.’ But that’s why I’m here, to help people.”

Weinstein’s recent reunion with Lipskar in Brooklyn took place just as the Aleph Institute’s “Rewriting the Sentence” summit was underway at Columbia University Law School in Manhattan. The groundbreaking gathering, held June 17-18, brought together some 400 leading jurists, including federal and state judges, district attorneys, members of Congress, probation and parole officers, academics and activists for multiple days of in-depth conversations about alternatives to incarceration. Weinstein, who has cut down on public appearances to preserve his energy for his work, did not attend, but over the course of the summit his name kept cropping up during speeches and presentations, uttered each time in tones usually reserved for rock stars.

Lipskar started the Aleph Institute after hearing the Rebbe comment at a Shabbat gathering not long after Passover 1981 that although much effort was being expended by Chabad activists to reach out to every Jew, there were hundreds or even thousands of Jewish people behind bars just waiting to be connected with, and no one dedicated to doing that work. The very next day, Lipskar, a longtime Chabad emissary who was already busy as executive director of the Shul of Bal Harbour, Fla., wrote a note to the Rebbe asking whether he should begin working with prisoners. The Rebbe—an early pioneer of criminal justice reform who in a number of public talks spoke of the fundamental flaw in incarceration disconnected from re-education and rehabilitation—responded with his emphatic blessing, and the Aleph Institute was born.


Ahead of the Curve

It was difficult in the beginning. The Bureau of Prisons was a massive bureaucracy, and just breaking in to the system proved difficult for the novice Lipskar, who needed advice and help. Weinstein, whose vast district includes Brooklyn—home to Lubavitch World Headquarters in the Crown Heights neighborhood—was already a towering figure in the criminal justice world. When the two met, Lipskar discovered an eminent, like-minded judge, while Weinstein saw in the young rabbi a fellow traveler. During their conversation, Weinstein learned of the Rebbe’s outlook on criminal justice—views that mirrored his own so closely. Over the next decade, Weinstein would take the opportunity to personally meet the Rebbe as well, encounters, he says, that have remained with him to this day.

“I was so honored to be in [the Rebbe’s] presence because not only did he have that fine grasp, which I didn’t have, of religion and the Jewish religion, but he was trained in secular matters,” Weinstein recalls. “He was brilliant in secular matters, and as a result, he could relate to our society and all its problems on the secular as well as the religious level.”

Weinstein receives a dollar and a blessing from the Rebbe, Rabbi Menachem M. Schneerson, on Dec. 17, 1989, as Rabbi Sholom Lipskar looks on. Weinstein was on his way to testify before the Federal Sentencing Commission. (Photo: Jewish Educational Media/The Living Archive)

In the early 1980s, something as elementary as a prisoner’s access to religious materials or even kosher food remained an uphill battle, with the government routinely denying such requests. And so, with Weinstein’s enthusiastic support, the nascent Aleph got to work reaching out to prisoners of all faiths and denominations and assisting them however it could with their spiritual, religious and personal needs.

But as incarceration in the United States continued to climb at alarming rates—and with it the belief that the nation could police and incarcerate its way out of the high crime and societal dysfunction rocking its urban centers, a process that has led to what is commonly known as “mass incarceration”—Aleph broadened its scope. Soon, it began advocating for sentences that would serve as meaningful alternatives to incarceration for all convicted individuals. In June of 1988, Aleph held its very first symposium, titled “Alternative Punishments Under the New Federal Sentencing Guidelines,” at Weinstein’s federal courthouse in Brooklyn. The conversation included Weinstein; Ilene Nagel, a commissioner on the Federal Sentencing Commission; J. Michael Quinlan, director of the Bureau of Prisons; David Trager, dean of the Brooklyn Law School; Lipskar; and others.

“The Aleph Institute, primarily operated by orthodox Jews, sponsored a conference on alternative sentencing along with Brooklyn Law School in my court in June … ,” Weinstein stated at a lecture later that year, subsequently published in the Albany Law Review. “It is doing extraordinary fine work. Its pre-prison counseling, in-prison education, and post-prison assistance to defendants and their families provide standards of compassion and aid worthy of emulation. Rabbi Sholom D. Lipskar, the guiding force of the Aleph Institute, and his associates understand and force us to face the fact that each and every person deserves to be treated with respect as an individual personality and not as an integer, a faceless number … ”

In these few short lines, which Weinstein would repeat countless times in the years to come, the judge underlined the Rebbe’s views on criminal justice, as reflected in the core mission of the Aleph Institute. Every single human being is created in the image of G d, no two alike, and each with their own mission in this world. The purpose of any correctional facility worthy of its name, the Rebbe stressed, was not merely to remove those convicted of crimes from society, but to correct their behavior by illuminating for them, through education, especially moral education, the path of responsibility, accountability, industry and achievement.

“If a person is being held in prison, the goal should not be punishment, but rather to give him the chance to reflect on the undesirable actions for which he was incarcerated,” the Rebbe said in Yiddish in a 1976 talk. “He should be given the opportunity to learn, improve himself and prepare for his release when he will commence an honest, peaceful, new life, having used his days in prison toward this end.

“In order for this to be a reality, a prisoner must be allowed to maintain a sense that he is created in the image of God; he is a human being who can be a reflection of Godliness in this world.”

The Rebbe, Weinstein asserts, was “miles ahead of the curve.”


‘You Will Support My Views?’

From the start, the Rebbe paid keen attention to the Aleph Institute’s every development.

Beginning in the mid-1980s, each Sunday the Rebbe would famously greet long lines of people from all walks of life, both Jews and non-Jews, outside of his office at 770 Eastern Parkway in Crown Heights and give a dollar bill meant for charity to each one. When Lipskar passed by, the Rebbe would invariably turn the conversation to Aleph.

“There was almost never a time when I passed by the Rebbe for dollars that he didn’t mention Aleph,” says Lipskar, who would also send the Rebbe regular reports on the organization’s activities. “He would give me a dollar especially for Aleph and say, in Yiddish, ‘For the entire Aleph,’ or ‘Aleph [the first letter in the Hebrew alphabet] guides all the letters that follow,’ or something of that nature.”

On Sunday, Dec. 17, 1989, Weinstein joined Lipskar in the dollars line to see the Rebbe, a brief exchange captured on video. Weinstein tells the Rebbe that the next day he would be meeting with the Federal Sentencing Commission, “and I am going to tell them your views on imprisonment.”

A judicial panel at the Aleph Institute’s Rewriting the Sentence summit in June 2019. The panel, titled “Judicial Practices: Creative Approaches to Sentencing,” featured, seated from left: Judge Fredric Block, U.S. District Judge, Eastern District of New York; Judge Virginia Phillips, chief U.S. District Judge, Central District of California; Judge Brooke Wells, U.S. Magistrate Judge, District of Utah; and Judge Esther Salas, U.S. District Judge, District of New Jersey. It was moderated by Rabbi Yossi Bryski, director of Aleph’s alternative sentencing division. (Photo: Meir Pliskin/Aleph Institute)

“You will support my views also, not only report my views?” the Rebbe quizzes him.

When Weinstein assures the Rebbe that he will indeed support them as well, the Rebbe tells him:

“May G d Almighty bless you to go from strength to strength, and to reach the time when there will be no prisons, only preventive education to prevent people from going astray from the right way.”

That evening, Weinstein and his children headed to Manhattan, where they took in a show at Lincoln Center. When it was over, the judge crossed the street to purchase a drink in a neighborhood bodega, outside of which sat a panhandler. Weinstein turned to his children and told him he had just the right money for the woman, the $2 for charity he had received from the Rebbe earlier that day. (Customarily, one who received dollars from the Rebbe would keep them and give an equivalent sum to charity.)

“What did you say, sir?” the woman asked him. “These came from the rabbi in Brooklyn? You can’t give away those dollars!”

Weinstein chuckles recalling the scene. “It was so incongruous.”

That Sunday wasn’t the first time Weinstein had met the Rebbe. Following the passing in early 1988 of the Rebbe’s wife, Rebbetzin Chaya Mushka Schneerson, Weinstein paid a shivacall.

“I’m here also on behalf of all the judges of the Eastern District, and it is our great honor to have the [Rebbe’s] presence in our district,” Weinstein told the Rebbe before wishing that he be “comforted among the mourners of Zion and Jerusalem.”

“May G d Almighty bless you to make all your judgements—and you are a judge over many judges—according to the real tzedek v’yosher [‘justice and honesty’], and it will be a [preface to the words of the prophet] ‘And I will restore your judges as at first,’” the Rebbe replied to Weinstein. “And certainly every judge of our times is contributing, by making the right decisions, to speeding up the fulfillment of the [prophet’s] promise that the highest court, the Sanhedrin Gedolah, will return [to its seat in Jerusalem] together with our righteous Moshiach.”

“I shall give your message to all the judges of our court,” responded Weinstein.

This experience, too, made an impression on the judge. Over the course of the week of shiva, countless public officials and Jewish leaders from across the spectrum came to pay their respects. This included rebbes from other Chassidic groups, many of them dressed in the traditional garb respective of their communities. Weinstein had never seen anything like it.

“There were groups of rabbis from all different—from all over the world—and it was like being in a medieval, feudal period,” says Weinstein. “I felt I had been picked up and flown back 400 years to medieval times—all these rabbis in their garments … each had different colors.”

For Weinstein, the Rebbe was a bridge between these seemingly different worlds, someone who connected age-old Jewish practice and thought with the modern era. That’s why neither the Rebbe’s advocacy for criminal justice reform nor Lipskar’s foray into that world as his representative struck the judge in the least.

“It didn’t surprise me because there’s so much of that kernel of goodness in 2,000 or more years of literature and learning and rabbinical wisdom,” observes Weinstein. “This was crying out for your help.”

The Kansas-born, Brooklyn-raised Weinstein has lived a long and momentous life. He enlisted in the Navy and served as a submariner in the Pacific theater during World War II, went to Columbia Law School on the G.I. bill—where he taught beginning in 1952—and was a member of the NAACP’s team of lawyers who successfully litigated Brown v. Board of Education, a monumental Supreme Court decision that found racial segregation in public schools to be unconstitutional. Nevertheless, so deep was the Rebbe’s impact upon Weinstein that when he gave a talk about his own life’s journey at the Brooklyn Historical Society and set up a map of Brooklyn with multicolored pins to denote important places in his life—the most influential places marked with red pins—he dropped a red one on 770 Eastern Parkway in Crown Heights.

“You know what this pin is?” he asked Lipskar at the time. “It’s the Lubavitcher Rebbe’s house!”



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