By: Benjamin Koslowe  | 

Lost and Found in Sing Sing: A True Story

The calendar may have suggested that spring was near, although the frothy rain clouds caressing the brown hilltops on the other side of the Hudson told a different story. It was a Wednesday, the first day of March, and we fifteen guys and girls from YU had just bussed up the river.

“Up the river.” As it turns out, we were standing in the place that inspired this expression. Sing Sing Correctional Facility – maximum security fences, watchtowers, and all – a gentle 45 minute drive north that hugged the east bank of the Hudson River, was our destination (I played music from The Shawshank Redemption to set the mood). The day was young but our short tour was already ticking away.

“Why did you come to visit prison?”

I was waiting for the group to finish being inspected for sharp items. The correct answer to the guard’s question would’ve been a full description of a close family connection that I have to the prison.

I had convinced the trip coordinator to give me a spot on the trip because of this connection. My great-grandfather, Rabbi Irving Koslowe (1920-2000), studied at Yeshiva University for almost a decade (YUHS ’36, YC ’40, Riets ’43, Revel ’43). Old Commentator archives from the 1930s document his talent as coach/captain of the Yeshiva College basketball team – headlines like “Koslovsky Stars” and “Koslovsky Scores” testify to his athletic abilities (and to his pre-Americanized surname). Soon after his rabbinical ordination he married Marly Schachter and moved to Mamaroneck, New York, where he took up a pulpit position at the Westchester Jewish Center. Though his main occupation for the next 44 years would be with the synagogue, the burden of supporting his young children plus a job opening led him to accept a chaplaincy role at Sing Sing in 1950.

The author (YC ’19) with his great-grandfather Rabbi Irving Koslowe (YC ’40), his grandfather Neil Koslowe (YC ’66), and his father, Jamin Koslowe (YC ’93).


Rabbi Koslowe gained national attention a few years into his career because of the Julius and Ethel Rosenberg trial. A Jewish couple convicted of espionage during the Cold War, the Rosenbergs were both sentenced to execution. My great-grandfather counseled them, recited vidui (confession) with them, and walked them to the death chamber. By the time that New York outlawed capital punishment in 1963, he had escorted 17 Jewish inmates to the electric chair.

But most of Rabbi Koslowe’s role was more focused on the enrichment of life, rather than the dignity at its end. His weekly visits consisted of helping the roughly 150 Jewish prisoners, including offering religious guidance, organizing meaningful prayer services, and ensuring kosher food for those who wanted. In 1959 he convinced the Sing Sing administration to let him convert a basement storage room into an independently Jewish place of worship. He named the chapel Beit Shalom V’Tikvah (the house of peace and hope) and furnished it with cheap red vinyl theater seats that were going to waste.

This attitude of restoring the seemingly unsalvageable defined Rabbi Koslowe’s career. In a 1992 interview with the New York Times, he described, “People ask me what I’m doing, bringing matzoh ball soup to a bunch of killers. But maybe we can make some change. Maybe we can bring some good in their life. Some of the guards would say I’m crazy, but I do what I can do.” He added, “If I can have an inmate come into the chapel, put on a yarmulke and worship, I think that shows there’s a positive change in behavior, a real step forward.” In 1999 he told the Times that his is one of the few congregations that “doesn’t mind losing members.” To this day there are ex-convicts who credit their life’s successful reformation to Rabbi Koslowe.

When Rabbi Koslowe retired in 1999 there were fewer than 40 Jewish inmates in Sing Sing. What began as a job that he envisioned lasting for only a few years had become a lifelong impactful career. He retired with 49 years under his belt, having served longer than any warden, guard, or prisoner to that time.

I was five years old when my great-grandfather passed away, so my few memories of him are hazy at best. I came to Sing Sing hoping to walk through the same cement halls and cell blocks that my great-grandfather paced for decades. Maybe one of the staffers would be able to share some recollections with me. Better, perhaps I could sneak a word with some long-time inmate who could tell me about his experiences studying Hebrew and Jewish tradition with Rabbi Koslowe.

But small questions deserve short answers, so all I responded to our guard and tour guide was, “I guess I want to see what prison is like.”

Rabbi Koslowe walking through a Sing Sing housing block.

(Photo Credit: Joyce Dopkeen/The New York Times.)


Looking back, I realize that my answer was not so far off from the truth of the matter. The prison tour was fascinating. We were guided upfront and close, walking through giant housing blocks with hundreds of filled prison cells that seemed to be stuck decades in the past, taken from some movie; seeing the shower facilities and exercise yards; standing outside the thick padded walls of solitary confinement quarters; hearing about gang violence against prisoners and guards. We witnessed what prison is like, gaining a valuable perspective on crime and punishment, the realities of domineering routine and institutionalism.

This would have been enough to warrant my skipping class for the tour. And then, before the tour concluded, we had extra time to visit the rooms of worship at the far end of the prison.

Chilly air drafted through the barred windows into the descending cramped basement staircase. After we organized single-file and turned a corner, I immediately noticed the chapel by its simple dedication placard: “Rabbi I. Koslowe.” On one of the walls was an article from some local Mamaroneck newspaper about my great-grandfather’s retirement. The article included a picture of a chess set, which my family still has, that some of Rabbi Koslowe’s acolytes carved by hand and presented to him as a gift. I pointed out the picture to our tour guide, who has worked at Sing Sing for almost 20 years, and he said that he remembered him.

While the red seats that our group occupied matched the descriptions, I was taken aback by the unexpectedly small size of the room. We nearly filled up the space.

The new chaplain, who took over in 1999 when Rabbi Koslowe retired, happened to be around that afternoon, so he stopped in to say a few words to us. He shared some Torah thoughts and updated us on Jewish life in the prison today. They (un)fortunately don’t usually have a minyan, but there are still some religious Jewish prisoners who request kosher meals, Passover seders, etc.

Of course I asked the chaplain if he remembers Rabbi Irving Koslowe. He confirmed that he overlapped a bit with that “good Yid,” and related some of the most famous Rabbi Koslowe prison stories.

“If I remember correctly,” he then told, “some time ago an old siddur of his turned up. I’ve been meaning to return it to his family, but never got around to it.”

“I’m actually Rabbi Koslowe’s oldest great-grandchild.”

“Oh. Do you want it?” It was that quick.

The chaplain unfortunately was unable to locate the prayer book in his small paper-filled office, but he wrote down my address and phone number in the hopes that he’d find it soon enough.

Soon enough proved to arrive almost immediately. No sooner than when we were walking outside around the inner cement walls back to the prison entrance did the rabbi hurry to catch up to us. He had found the siddur. He asked our guard if I may take it out of the prison. The guard flipped through the book, established that it was not contraband, and gave me my great-grandfather’s Sing Sing siddur to take home.


The end of the prison tour is a bit surreal in my mind. The group clapped when I was handed the siddur. I remember opening it up by the bus and flipping to recite psalm 23 – “gam ki elech begei tzalmavet,” “even as I walk down the valley in the shadow of death” – with the death row house and iconic “last mile” path in full sight.

In an email that I wrote on the bus to my family I described how the experience bridged generations, connecting me a bit more to my great-grandfather whom I never really knew. And yet, I found myself with writer’s block on this story. For several weeks I had difficulty organizing my thoughts.

As I was leaving YU for Pesach, I picked up the siddur for the first time since the trip. We were going to spend the holiday with our great-grandmother, Grandma Marly Koslowe (who is 96 and has 54 great-grandchildren, as well as an outstanding memory), and I figured that she would want to see the object for herself.

I showed her the siddur on erev Yom Tov, just a few hours before the first seder. The siddur is small, with dimensions about the size of a normal adult hand. My Grandma immediately noticed that the siddur’s binding was restored with band aids. She told me that this was typical of my great-grandfather, who apparently used to regularly mend old novels and checkbooks that would otherwise fall to disrepair. And she also estimated, based on the wear, tear, and printing date that this was probably his prison siddur from the beginning of his service in 1950. Likely he misplaced it at some point before his retirement; only now, 67 years later, was the siddur liberated from the realm of maximum security.