Power of Hope: Aleph Volunteer Inspires “Lifer” in Prison

Reuven Overlander met his first life sentence inmate when he was 23 through Aleph Institute’s Summer Visitation Program. Through their relationship and learning, miracles happened.

By Reuven Overlander – aleph-institute.org

The first time I entered a prison, I was 23 years old. It was July of 2009, and I was volunteering for Aleph’s Summer Visitation Program together with a good friend. We road-tripped through North Carolina, South Carolina, and Georgia, visiting Jews in various prisons and trying—to whatever extent possible—to bring a little hope and happiness into a very dark place. 

Every aspect of prison, from the gray walls to the frigid temperature, seems designed to drain the life out of you, literally. While visiting Wilcox State Prison, I met Jack.*

Jack was a “lifer,” someone serving a double life sentence, with no chance of getting out. He told me, “Every night, I pray to G-d with all my heart that He should just take my soul away. I have nothing to live for, and every morning I wake up devastated that he hasn’t fulfilled my request.”

I had never seen anyone so broken. So bitter. And sadly, so realistic.

I don’t know what compelled me, but I began to tell him the biblical story of Joseph, who was trapped in an Egyptian prison and ended up becoming Pharaoh’s Second-in-Command, all because he opened a meaningful conversation with his non-Jewish “celly.” I explained that although we don’t know why Hashem puts us in a specific place, the fact that we wake up in the morning is proof that there is something meaningful for us to live for. I also said, “G-d is the true Judge and He is the One who writes sentences. Even if according to nature you have no chance of getting out, G-d can make anything happen.”

As I spoke and saw Jack listening deeply, I began to feel nervous. What if I am giving him false hope? But it was too late. I had said what I said. After a few hours, it was time to say goodbye.

The next year, I volunteered for Aleph’s Summer Visitation Program again. Although I was given a different route, a part of me wanted to go back and see how the people I had already met were doing. So I decided to do two cross-country trips, one on a new route and one on last year’s route. 

When I walked into the same room at Wilcox, Jack did a double take. “Wait, aren’t you the guy who came last year?” he asked. I told him I had come to see him again. Jack’s eyes filled with tears. “In the ten years that I have been receiving visitors every summer, nobody has ever come back,” he said. “Last year, I told you I wanted to die,” he continued. “But you won’t believe it—I’ve just been granted permission to serve my double life sentence on double-time. That means after 25 years, I will be eligible to see a parole board. For the first time since I got here, there is an end in sight.”

For many years after that, I repeated Jack’s story to countless others in the 250+ prisons I visited. Many other incarcerated men and women were uplifted and heartened by his message of hope. 

Fast-forward to 2022. This year, I returned to Wilcox Prison on my route for Aleph’s Summer Visitation Program. I was given a list of all the inmates who would attend the service. I saw Jack’s name but it did not register in my head. When I saw him, my heart sank. 

So much for my story, I thought. I repeated it to so many people, yet here we are a decade later and Jack is still stuck in this miserable place.

I recognized Jack, but he did not recognize me. (A lot can change in 13 years.) I was thinking of not mentioning anything but then I thought: His story has helped so many people, I owe it to him to tell him.

So I reminisced about our previous meetings, which he remembered well. I said, “Jack, I just want you to know that your story has inspired countless others. You have made a difference in the lives of strangers you never even met.”

Jack replied, “And I just want you to know that after all this time, I am about to go out on parole. I am about to be free.”

With tears streaming down his face, Jack put on Tefillin and prayed to G-d with all his heart. This time, he was not asking Him to end his life, but to bless him with a new beginning.

To help support Aleph’s work visiting prisons and its year-round programs, go to www.aleph-institute.org/donate.