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During the High Holidays, many Jews take a seasonal introspective dive, asking themselves who and what is most meaningful in their lives. For my mother, one answer is her relationship with incarcerated Jews.

For the past decade my mother has participated in the Aleph Institute’s Prison Writing Program, which matches “Jews on the inside with Jews on the outside.” Her pen pals have included men and women incarcerated on charges of manslaughter, first-degree murder, assault and battery, identity theft, and larceny. In their letters, they discuss Israel and aspects of Jewish life, but what is most meaningful to both is the introspection, reflection, and perspective they engage in with each other.

For many prisoners, deep searching, reflection, regret, and attempting to mend the broken parts of their lives isn’t just a High Holiday undertaking. It’s all the time. And it’s done without the benefits of community, pristine white clothes, or dinner tables laden with traditional food. They write to my mother about the indignities of prison life, feeling abandoned by families and friends, shame and regrets about their decisions, as well as claims of innocence. She shares with them the activities of her daily life, like meditation and interfaith work, and a few details about her family.

The other night, my mom told me about a recent phone call she had with Joel (not his real name), a middle-aged man incarcerated for larceny, with whom she has been exchanging letters for nearly a decade. “He had a lilt in his voice,” she told me. “He first asked about our [recently renovated] kitchen: Was the work done? Were we happy with it? Then he really wanted to tell me what I meant to him, to express gratitude and appreciation.”

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Jews constitute a tiny fraction of America’s penal system population: about one half of 1 percent of the more than 2 million people incarcerated in this country. (That’s an estimated total of 6,000 to 12,000 Jewish prisoners, although the count is inexact because religious affiliations are self-reported in jail, and many choose not to identify or identify falsely in order to get a kosher meal.) There are several organizations devoted to serving the religious, spiritual, educational, dietary, and legal needs of Jewish prisoners. There is Reaching Out, a Chabad group, whose mission states it is “on the forefront in bringing the light of the Torah to the darkest places of the prisons.” There is the National Association of Jewish Chaplains, a worldwide organization that trains and supports some 300 members who minister to Jews in hospitals, hospices, prisons, mental-health institutions, and the military.

Then there is the Aleph Institute, which exists to serve the religious, spiritual, educational, dietary, and legal needs of Jews in prisons, in nursing homes, and in the military. My mother discovered its letter-writing program 12 years ago in a now-defunct Jewish newspaper in Boston. She emailed the coordinator, a man living in New Zealand, who matched her with Joel because of shared interests in yard sales, Jewish learning, and medicinal herbs.

Joel had been in prison for two years when he first received a letter from my mother. He had recently been jumped by three inmates in the bathroom and used a pen he had in his pocket to defend himself. For this, his sentence was extended by a year, and he was put into solitary confinement, “the hole,” for several weeks. Many Jewish inmates, Joel included, are ostracized by family, friends, and religious communities when incarcerated. They feel utterly alone and abandoned and often experience anti-Semitism in prison from guards and other inmates. In a recent letter, Joel recalled the beginning of their relationship: “When I got out of the hole it was waiting for me. I was at the lowest point in my existence. I had given up on tikvah, and was letting myself slip into a darkness that I had never experienced before. I had no connection to the outside, except for the monthly newsletter from Aleph. That changed on the 16th when I awoke to find a letter stuck in my door. … I opened it and read, then re-read it. I thought, why would this woman, whom I did not know, write me, when the only thing that we shared in common was the fact that we were Jews? Then it dawned on me—that was the sole reason for the letter, one Jew reaching out to another … it meant a lot.”

At first, Joel’s letters described the indignities of prison life and, because he knew my mother liked art, he enclosed in the envelopes colored-pencil sketches: roses, a portrait of Barack Obama, a Jewish star. My mother sent back cards with reproductions of famous art. When my mother had sciatica, he researched herbal remedies and sent her pages of carefully written instructions for natural cures. After a year or so, he started talking about the dysfunction and abuse in his family and how even though he was a paralegal he could never make enough money.

Slowly he became more trusting and open to taking advice. My mother sent him Houses of Healing, a book written for inmates to re-form their identities in positive ways. They used the book as a focus of their conversation, and after several months he wrote to her: “I see a psychologist, a Jewish chaplain, but none help me in the ways that you did with and through the messages of this book. I believe that I have some potential to lead a different life.”

When Joel was released from prison for a brief period last March, my mother sent him money (which Aleph discourages) to stay in a hotel, so he’d have a safe bed and shower for at least a few days. For several months he lived in a shelter, until he got into a fight on the street when, he claims, he was protecting a woman from a man who was harassing her. Joel was sent to jail for a few days, and when he got out the shelter wouldn’t take him back. He stayed with an old friend whom he had helped years before, and she helped him find a job. My mother sent him sheets so he wouldn’t have to sleep on the bare floor and presents to celebrate his new start.

He wrote to her: “I was sitting in my room and opened the package filled with chocolate, colored pencils, and other goodies that you wanted me to enjoy, and I thought, someone cares enough about me to send this. Even though I’ve been out of prison for months, it was the first time that I felt joy. I do not experience that feeling much. For me, [your support] means community and a sense of belonging. It helps.”

After working for several months, Joel was able to rent his own apartment, but he was soon in another fight that sent him back to jail. In the Midwestern state where Joel is from, where he now must stay because of parole regulations, there are few programs to help support ex-prisoners to reintegrate into civilian life. He expressed his frustration that if he were an addict or a pedophile, there would be groups to attend and programs for support, but as a man who has no family or friends to rely on, no money, and a prison record, he is on his own.

He wrote to my mother: “What does the state have to offer me so that I can have a life and be accountable as they want me to be—but how—on the streets with no money? … I am physically out of prison but my mind is still shackled from the abuses. My vision [of myself] is that of a man in the streets with the clothes on my back, not two pennies to rub together, no way to get food or warm clothing, having to sleep out in the elements with nowhere to turn. Do I go shoplifting to get sustenance? Do I cuss and threaten my agent so she will throw me back in jail where I have at least three hots and a cot?”

My mother explained to me, “Many prisons used to focus on rehabilitating criminals to society after a prison sentence, but now prison in this state is primarily punitive. His identity is still as an ex-con because that’s how he sees the world seeing him. He has no work history. He wrote to me recently: ‘Everyone sees me as an ex-con, no one trusts me, so what chance do I have?’ ”

She continued, “I’m giving him moral and minimal financial support. And it’s not enough. I was in the position to help him in the healing process because using the book and his interest in Judaism which allowed me to introduce themes of teshuvah, ‘missing the mark,’ going through narrow places, all of which seemed to help him, but now he is too burned out, scared, and just surviving and not able to access what we did when he was in prison. His inability to cope and survive on the outside is a constant challenge now which leaves him feeling hopeless.”

Joel recently wrote asking my mother if she thought he was a bad person. He went on to say, “I feel that I’ve terribly disappointed you and the investment you’ve made in me, and that I’ve fallen short of the intended goal. So now I’ve become a derelict, a bum, with nowhere else to turn besides the prison gates that I just came through. I also know that I am a disappointment to the Jewish community for not being bigger than I am now, but not being able to find the tikvah I need. I look inward and am having a hard time seeing its light.”

She replied that she feels he is a good person who wants to do good, but who’s been the victim of difficult circumstances. She said, “I wrote to Joel about the Israeli national anthem, ‘Hatikvah,’ that if Jewish people can sing about the hope of 2,000 years, I’m wishing that he can find the hope to start over, too. He responded, ‘I don’t have the luxury of hope.’ ”

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My mother has corresponded with six Jewish inmates over the years. She visited and wrote to three women for one year each. But her long-term relationships have been with men. In addition to Joel, she wrote to a man who’d been incarcerated for manslaughter. Upon his arrest, his wife divorced him and his friends turned their backs. Released from prison at age 71, he started life anew, with the support of one sister. He and my mother still exchange occasional letters, cards, and speak on the phone. My mother’s third long-term pen pal has been living on death row in San Quentin for the past 20 years, after being convicted of murder.

My father became involved in the program a few years after my mother. He has now been writing, speaking by phone, and visiting with two of the men my mother writes to. In one case the inmate admitted his crime, the other denies that he committed the crime. “In both cases, I have seen the importance of functioning as a friend, to support a person in need,” my father told me. “Although I abhor murder as anyone would, I am surprised to find myself instinctively compassionate and wanting to help these people who are suffering deprivation, despite the horrible act they committed, or might have committed.”

There is no way for my parents to verify or disprove what their pen pals tell them. Ten years ago, when my mother first started writing to inmates, she used a false name and rented a P.O. box at the Post Office. The Aleph Institute offers that many beginning letter writers feel more comfortable with their identities concealed. Aleph also reports that after a while most pen pals, as was the case with my mother, choose to reveal their real names and home addresses once they believe that the incarcerated person is a person they can trust, even if they’ve made bad choices in the past, or have been victims of poverty, abuse, mental illness, or desperation. I asked my mother how much she can believe what Joel tells her. She said, “I don’t know, I’ll never know the truth, but the way he responded to Houses of Healing, he got it. And the way he shows sincere appreciation and gratitude for my letters and support, he really wants to do better.”

Jews have many customs to help with the difficult work of turning inward, taking stock, and asking for forgiveness both human and divine. We dip apples in honey, gather with family and friends, chant in sanctuaries, and throw bread in the waters of our towns. Some Jewish prisoners receive apples and honey, challah, and grape juice from Jewish programs or prison chaplains, but mostly they mark the High Holidays alone. My mother’s impressions are that spending the holidays incarcerated emphasizes their imprisonment and their separation from everything familiar and festive, so it is not an emotionally peaceful time. She said, “A few prisoners express appreciation for the chaplains and the prisons’ attention to special kosher meals, but in general it is not a celebratory time.”

She sends her pen pals cards and readings with reflections about teshuvah and how important it is for them to forgive themselves and to try to forgive those who betrayed or hurt them. The death row inmate sends my parents very elaborate cards he paints in the confines of his narrow cell. The man who was released at 71 sends them holiday cards with messages of appreciation. Joel, currently in jail for breaking parole, is cut off from a chaplain and attention to the holidays and their themes. He calls my mother frequently now, collect, from jail, and speaks with a mixture of sadness and despair in response to her encouragement to find tikvah, hope, even in these dark times.

While going over some final clarifications for this article, my mother received a belated birthday letter from Joel. She read me a portion over the phone: “My pen pal later became my friend, confidant, mentor, but most of all, the sister that I never had in my life. The eight years I have known her and her husband she has been an anchor, and at times the very voice of reason that I needed when it was apparent that I was going to act on impulse and make my situation only worse. … I am fortunate to have them in my life, they have stood with me through the trials and tribulations that I have had to deal with in an unjust system. I know that at times I just want to give up, but I am asked by her, encouraged by her, and at times, pushed to the point of frustration to be that better person that I can be. She continually challenges me to this day to look inward and deeper, to look for a solution to the problem instead of creating one. I know that this person will never realize how much tikkun she has done for my olam. And for this, she has my love and profound appreciation and gratitude.”

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