True and Eternal Teshuva
IllumniNations | September 26, 2024
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True and Eternal Teshuva

IllumniNations | June 27, 2025

My wife’s vision has infected me to see how much our organization can grow and continue to help many others.

When I first started visiting prisons, I was a young man of 25. One of the first inmates I grew close with was Shimon*, a teenager who’d been convicted of first degree murder against a classmate. Shimon was in a bad state when I first found him. He was looking at a 14-year sentence, where he’d spend the best years of his life behind bars. He was despondent, not seeing the use of doing anything with his wasted life.

When I spoke with him, I sensed something underneath the hardened criminal - a Jewish neshama, crying to be set free. I visited him a few times a week, bringing him kosher food and books of Jewish philosophy to read.

By the time Shimon turned 18 and was transferred out of juvie, he was already wearing a yarmulkah and tzitzis. The prison guard stared in disbelief; in all their years, they’d never seen a prisoner dress like that.

I continued visiting him and saw that Shimon was undergoing a deep, genuine teshuva. He worked on himself to root out his darkest traits, and was extremely remorseful about his past actions.

When Shimon’s case was put under review, the court unanimously agreed to release him early for good behavior. Shimon was duly appreciative and grateful to begin a new life while still relatively young. He immediately enrolled in a baal teshuva yeshiva, and completely turned his life around.

Shimon’s first marriage ended in disaster a few short months after the wedding. His wife was abusive, and the violence began during sheva brachos week!

Shimon would call me, in tears. “What do I do, Rabbi? Why is this happening to me?”

I couldn’t know for sure, but I tried to comfort him with this thought: “The Rambam says that the greatest sign of a complete teshuva is when you’re presented with the same opportunity, but manage to overcome your yetzer. The fact that you’ve never raised a finger to your wife, no matter what she’s done to you, is a sign that your rehabilitation is complete.”

My wife’s side of the organization can be the hardest, most heartbreaking part of it all. She’ll often talk to mothers, sisters, brothers, and friends of the accused, whose only crime is being related. Yet they often cry about the isolation they feel, as everyone in the community turns their backs on them and glares at them as if it was their hands that committed the deed.

When trying to rehabilitate former detainees into society, we hit roadblock after roadblock. No one can look past the “convict” description to see the reformed and eager human underneath. Their families won’t accept them back, and finding a job is next to impossible. It’s heart-rending to hear story after story, knowing there’s only so much we can do to tear down such strongly built prejudices.

My wife went with one recently released man to get some basic pieces of clothing. Still unused to the ways of the world, he mentioned - rather loudly - that he’d just spent 20 years in prison. She tried shushing him, especially when the man in front of him turned around and looked him up and down.

“I did 10 years, myself!” he said. “Here; take these pants. You need them more than I do.”

The simple gesture brought tears to my wife’s eyes. It was clear that the man needed them too, but he didn’t hesitate to give them away.

Another time, my wife was trying to get an agency to help Sonia*, a woman who’d spent 17 years in prison for murder.

“We’re too scared to accept her as a client,” they refused. “She’s dangerous, and a liability to our staff and other clients.”

“Just meet her once, please,” my wife begged. They finally agreed, and were shocked when my wife led in a frail, elderly woman, ambulating with difficulty even while clinging to her walker.

“Look at my bobble earrings!” Sonia excitedly showed the staff. “Aren’t they adorable?”

Needless to say, sweet Sonia has become one of their favorite clients.

Michelle* was a Fulbrite scholar with an MA - and also a bipolar diagnosis. One of her episodes led to her sending someone numerous texts. They complained to the police, and she was arrested for harassment. She awaited sentencing for 18 months, living in inhumane conditions that only worsened her illness. When her case finally reached the docket, it was immediately dismissed and she was released. But the damage had already been done.

There are so many stereotypes working against these people. We wish more people would learn from the Rebbe’s example on how to treat people who are learning how to adjust to a whole new world.

My wife went to visit Lynn* in a halfway house, whose conditions were only slightly better than the prison she’d just left.

Lynn was overwhelmed with gratitude upon receiving the food and clothes my wife brought her, and they chatted for a little while. My wife couldn’t help but notice the cross dangling from Lynn’s neck. Lynn herself had told my wife she’d grown up in a traditional Jewish home.

“How sad,” my wife thought to herself. “This poor neshama is so distant from her faith and heritage, she feels like her only symbol of hope and protection is a cross. Maybe I can do something to rekindle her faith.”

Aloud, she said, “Can I teach you a special prayer called Shema? It’s about -”

Lynn interrupted her with a flawless recitation of Shema, as she’d learned it as a little girl in Hebrew School.

Tears filled my wife’s eyes. “Who am I to lecture her on faith and suffering?” she thought. “She’s been through so much turmoil, and yet Shema is still on the tip of her tongue after all these years.”

I remember receiving a call, asking me to visit a family still reeling from a traumatic event. Sarit’s* husband, while in the throes of a mental health collapse, tried to “exorcize the demons” from their baby. While the police took him into custody, Sarit and her remaining four children had nowhere to go. They didn’t want to stay in their home, the scene of so much trauma, but they didn’t know what other options they had.

I immediately drove to their home and packed the family in my car. We treated them to kosher pizza - the first of their lives - and brought them to our home. My wife, Hinda A”H, a born teacher, engaged the children and tried to distract them from their trauma. They spent that whole Shabbos with us, and we did our best to stay upbeat, positive, and cheerful. It was the childrens’ first time seeing an Aron Kodesh and Torah, hearing kiddush, and making havdalah.

They moved to Eretz Yisroel a short while later, and I lost touch with the family. I continued visiting the father in jail, but his mental health hadn’t improved, and it was nearly impossible to hold a coherent conversation with him. When he passed away a few years later, we were able to arrange a Jewish burial for him.

25 years later, I got a call from the wife of Sarit’s youngest son. They’d recently moved back to America, and her husband was interested in learning more about what happened to his father. Through them, I found out Sarit’s children had all integrated into Torah-observant schools, and were all leading Torah lives. Our interference over one Shabbos derailed a path of destruction in its tracks, and instead turned it into a force for good. We can never know how great an impact our little actions can have.

*Names changed to protect privacy

My wife’s vision has infected me to see how much our organization can grow and continue to help many others.

When I first started visiting prisons, I was a young man of 25. One of the first inmates I grew close with was Shimon*, a teenager who’d been convicted of first degree murder against a classmate. Shimon was in a bad state when I first found him. He was looking at a 14-year sentence, where he’d spend the best years of his life behind bars. He was despondent, not seeing the use of doing anything with his wasted life.

When I spoke with him, I sensed something underneath the hardened criminal - a Jewish neshama, crying to be set free. I visited him a few times a week, bringing him kosher food and books of Jewish philosophy to read.

By the time Shimon turned 18 and was transferred out of juvie, he was already wearing a yarmulkah and tzitzis. The prison guard stared in disbelief; in all their years, they’d never seen a prisoner dress like that.

I continued visiting him and saw that Shimon was undergoing a deep, genuine teshuva. He worked on himself to root out his darkest traits, and was extremely remorseful about his past actions.

When Shimon’s case was put under review, the court unanimously agreed to release him early for good behavior. Shimon was duly appreciative and grateful to begin a new life while still relatively young. He immediately enrolled in a baal teshuva yeshiva, and completely turned his life around.

Shimon’s first marriage ended in disaster a few short months after the wedding. His wife was abusive, and the violence began during sheva brachos week!

Shimon would call me, in tears. “What do I do, Rabbi? Why is this happening to me?”

I couldn’t know for sure, but I tried to comfort him with this thought: “The Rambam says that the greatest sign of a complete teshuva is when you’re presented with the same opportunity, but manage to overcome your yetzer. The fact that you’ve never raised a finger to your wife, no matter what she’s done to you, is a sign that your rehabilitation is complete.”

My wife’s side of the organization can be the hardest, most heartbreaking part of it all. She’ll often talk to mothers, sisters, brothers, and friends of the accused, whose only crime is being related. Yet they often cry about the isolation they feel, as everyone in the community turns their backs on them and glares at them as if it was their hands that committed the deed.

When trying to rehabilitate former detainees into society, we hit roadblock after roadblock. No one can look past the “convict” description to see the reformed and eager human underneath. Their families won’t accept them back, and finding a job is next to impossible. It’s heart-rending to hear story after story, knowing there’s only so much we can do to tear down such strongly built prejudices.

My wife went with one recently released man to get some basic pieces of clothing. Still unused to the ways of the world, he mentioned - rather loudly - that he’d just spent 20 years in prison. She tried shushing him, especially when the man in front of him turned around and looked him up and down.

“I did 10 years, myself!” he said. “Here; take these pants. You need them more than I do.”

The simple gesture brought tears to my wife’s eyes. It was clear that the man needed them too, but he didn’t hesitate to give them away.

Another time, my wife was trying to get an agency to help Sonia*, a woman who’d spent 17 years in prison for murder.

“We’re too scared to accept her as a client,” they refused. “She’s dangerous, and a liability to our staff and other clients.”

“Just meet her once, please,” my wife begged. They finally agreed, and were shocked when my wife led in a frail, elderly woman, ambulating with difficulty even while clinging to her walker.

“Look at my bobble earrings!” Sonia excitedly showed the staff. “Aren’t they adorable?”

Needless to say, sweet Sonia has become one of their favorite clients.

Michelle* was a Fulbrite scholar with an MA - and also a bipolar diagnosis. One of her episodes led to her sending someone numerous texts. They complained to the police, and she was arrested for harassment. She awaited sentencing for 18 months, living in inhumane conditions that only worsened her illness. When her case finally reached the docket, it was immediately dismissed and she was released. But the damage had already been done.

There are so many stereotypes working against these people. We wish more people would learn from the Rebbe’s example on how to treat people who are learning how to adjust to a whole new world.

My wife went to visit Lynn* in a halfway house, whose conditions were only slightly better than the prison she’d just left.

Lynn was overwhelmed with gratitude upon receiving the food and clothes my wife brought her, and they chatted for a little while. My wife couldn’t help but notice the cross dangling from Lynn’s neck. Lynn herself had told my wife she’d grown up in a traditional Jewish home.

“How sad,” my wife thought to herself. “This poor neshama is so distant from her faith and heritage, she feels like her only symbol of hope and protection is a cross. Maybe I can do something to rekindle her faith.”

Aloud, she said, “Can I teach you a special prayer called Shema? It’s about -”

Lynn interrupted her with a flawless recitation of Shema, as she’d learned it as a little girl in Hebrew School.

Tears filled my wife’s eyes. “Who am I to lecture her on faith and suffering?” she thought. “She’s been through so much turmoil, and yet Shema is still on the tip of her tongue after all these years.”

I remember receiving a call, asking me to visit a family still reeling from a traumatic event. Sarit’s* husband, while in the throes of a mental health collapse, tried to “exorcize the demons” from their baby. While the police took him into custody, Sarit and her remaining four children had nowhere to go. They didn’t want to stay in their home, the scene of so much trauma, but they didn’t know what other options they had.

I immediately drove to their home and packed the family in my car. We treated them to kosher pizza - the first of their lives - and brought them to our home. My wife, Hinda A”H, a born teacher, engaged the children and tried to distract them from their trauma. They spent that whole Shabbos with us, and we did our best to stay upbeat, positive, and cheerful. It was the childrens’ first time seeing an Aron Kodesh and Torah, hearing kiddush, and making havdalah.

They moved to Eretz Yisroel a short while later, and I lost touch with the family. I continued visiting the father in jail, but his mental health hadn’t improved, and it was nearly impossible to hold a coherent conversation with him. When he passed away a few years later, we were able to arrange a Jewish burial for him.

25 years later, I got a call from the wife of Sarit’s youngest son. They’d recently moved back to America, and her husband was interested in learning more about what happened to his father. Through them, I found out Sarit’s children had all integrated into Torah-observant schools, and were all leading Torah lives. Our interference over one Shabbos derailed a path of destruction in its tracks, and instead turned it into a force for good. We can never know how great an impact our little actions can have.

*Names changed to protect privacy

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