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A Friend in Prison

A holiday celebrating freedom is a good time to remember those who aren’t free

Annette Gendler
April 02, 2020
Tablet Magazine
Tablet Magazine
Tablet Magazine
Tablet Magazine
This article is part of The Many Meanings of Freedom.
See the full collection →︎

“So we have friends in prison now?” my daughter, home from college, said as she studied the address on the powder-blue envelope on top of our outgoing mail pile.

“We do,” I responded, slightly embarrassed. That powder-blue envelope contained my Passover card to—yes, a friend in prison. It was a fairly new thing for me, too. This friend had been convicted of money laundering, mainly by virtue of having the wrong boyfriend.

When my husband and I first heard that she had landed in prison, we had brushed it off as nasty gossip. In prison? Couldn’t be true! In our circle nobody landed in prison. I even checked her Facebook account and found her last post had been fairly recent. We had known this friend quite well many years ago when we lived in the same city. Now we live in different countries but we had been loosely in touch via Rosh Hashanah and birthday wishes, and Facebook likes and comments.

Sometime later, while sitting shiva for his brother, my husband reconnected with people from the old days and found the rumor confirmed. This particular friend was indeed in prison and was having a hard time of it. Who wouldn’t? A mutual friend told us that she was desperate for news from the outside world, so I sent her a Hanukkah card. We have been pen pals ever since.

I discovered that corresponding with a prisoner entails all kinds of hurdles, particularly if you send anything other than a piece of paper and an envelope. For example, when I sent her printouts of my blog posts, they were held up because they looked like magazine articles, which are restricted. I sent her books, only to find out that she was allowed only a certain number of books in her cell. One book-mailing sent straight from Amazon reached her, the other didn’t. She didn’t always have the funds to buy stamps or paper and envelopes to write back. There’s an “emailaprisoner” system where I pay to have an email delivered to her. For an extra fee, she receives a sheet of paper to write her response on, which is scanned and emailed to me. In two instances, however, the messages I paid for never reached her. In the meantime I have settled on a mix of emailing and sending physical cards, postcards and letters. Even if an email is faster and cheaper, I feel snail mail, with its handwriting, images and stamps, has more soul. It is a more tangible token of the outside world.

Two years into supporting my friend in prison, I have learned a lot more about prison life, something I had until then only known from clichés in movies. I have also visited her twice on my travels, an experience less unpleasant than I thought it would be. On my most recent visit, she arrived in tears. She was upset because the guard had come late to pick her up from her cell, and she thus missed out on 10 precious minutes of our visit.

After we hugged each other she said: “Sit on the blue chair.”

I looked at her puzzled.

“It’s one of the rules. Prisoners sit on the red chairs, visitors on the blue ones.”

I hadn’t noticed that on my first visit, when my friend already awaited me, seated on the proper red chair.

While her prison seems pretty amiable, it is a place full of such restrictions and rules. The women running the little kiosk where I bought a muffin for my friend and coffee for myself were downright chatty and fun. They are volunteers, my friend explained. I could buy stuff at the kiosk, but prisoners can’t. Visits take place in what feels like the multipurpose hall of a day care center, with groupings of blue and red upholstered chairs and a play area for prisoners with children. My friend showed up in leggings, sneakers and a loose plaid shirt—no orange is the new black here. Visitors are not permitted to bring anything along, aside from some money: no purse, no gift for my friend, not even the scarf around my neck. And yet, the people at the reception are friendly and helpful. My friend had even been able to arrange for me to leave my luggage at the front desk, given that I was coming straight from the airport.

I knew the routine from my first visit: Show up at least 15 minutes before visitation time. Those hours are strict and cannot be changed. Put everything into a locker, including the 21st-century human’s most prized possession, the smartphone. Check in with your fingerprints, which in my case were already in the system from my previous visit. Then go through a metal detector and a body search with a wand wielded by another friendly clerk. Wait with other visitors by a heavy glass door, which eventually slides open to a loud buzz. Proceed into a compartment where you wait until the first door closes and a second door opens to another loud buzz. Enter what looks like a high school gym waiting area with cinder block walls painted a shiny pale yellow. Plastic bowl seats are screwed into the floor, and restrooms have to be unlocked by a guard. Visitors waiting with you keep checking their watches as time has ticked by 2 p.m. when visitation officially begins. Soon enough you line up to go through another door and another supervised fingerprint that opens a turnstile and ushers you into the large multipurpose hall with its blue and red seats, and the kiosk in the corner.

Hearing about and witnessing some of my friend’s life in prison has given me an appreciation for my personal freedom which I took for granted, even more so than good health, safety, and shelter. I’m often confronted with health challenges, either my own or those of others. Safety is on my mind every time I walk home in the dark in Chicago, or when I use my pass card to buzz myself into the Jewish school where I work. I encounter enough homeless people in Chicago to be aware of the gift of shelter. But personal freedom? I just never thought about what it would be like not to be able to get up when I want, eat what I want, wear what I want, talk to whom I want, read what I want, say what I want, and walk out the door when I want. My friend has none of that.

Which is, of course, the point of prison.


Passover is a celebration of freedom, which until now I always associated with freedom from political oppression and slavery, not with prison. How do we as Jews deal with prison? In a prison of about 600 female inmates, my friend is currently the only Jew. A rabbi visits her regularly, and she is thankful to study Torah with him. My friend always had a good heart, and despite her stunning beauty, she was always nice to everyone. Nevertheless, before prison, she was preoccupied with the “in” stuff: the hottest nightclubs, the latest fashion, the best restaurants. All that means nothing in the world behind bars. It is her good heart and the Judaism she grew up with that sustain her now.

“I believe,” she told me, “that God put me here for a reason. Maybe life would have gotten a lot worse for me on the outside given that my boyfriend was a criminal. Or maybe God put me here to help others.”

And that she does, volunteering as a listener, i.e., someone who gets woken up in the middle of the night to listen to another inmate who is having a hard time, often on the verge of suicide. She also works with the imprisoned mothers with babies. In addition, she takes every possible class she can, trying to make the best of what could end up being five years in jail.

Fellow inmates often ask her why so few Jews land in prison, so being incarcerated as a Jew feels particularly shameful. Even knowing someone in prison felt shameful to me. When I first began writing to my friend, I found myself shielding the envelope from view when I walked to the mailbox, lest one of my neighbors see it. Once I ran into one of them at the mailbox and got all flustered, trying to make sure he wouldn’t see the address on my envelope.

If I felt this way about merely popping an envelope into the mail, how must my friend’s son feel? What does he say when he has to explain to what his mother is up to? In our social circles knowing a prisoner just isn’t a thing. People suffer plenty of troubles and tragedies, but prison? And how much worse must it be if you are that person? What shame must my friend be dealing with? While I was grappling with this, I happened upon a passage in Rebbetzin Esther Jungreis’ book Life Is a Test that addressed the issue of Jews in prison. For all our troubles, writes Jungreis, there is an example in the Torah that we can learn from. She shared an anecdote of providing hope to parents whose son had landed in prison for drug possession. She told them the story of Joseph, who had spent many hopeless years in an Egyptian dungeon without ever giving up his humanity and his belief in God. In the end, he made a connection there that would help him be freed later. The Chamberlain of the Cupbearers remembered that Joseph had correctly interpreted a dream for him when they were imprisoned together and recommended him to Pharaoh (Genesis 39-41). I copied those passages and sent them to my friend.

In prison, my friend says she has learned to appreciate the smallest things: Making a few pennies to buy nail polish. A kosher meal that isn’t the same as all the others. A postcard from a friend.

These days, I am not timid anymore when I carry my letters to her to the mailbox. Rather, I am glad I can support her in some small way. Mainly, however, I relish the very fact that I can step out of my house and walk down the street to mail a letter. Because that already is a freedom to celebrate.

“I miss my garden the most,” my friend told me on my recent visit. “To be able to sit outside again, with a cup of coffee—that is all I want.”

Annette Gendler is the author of Jumping Over Shadows, the true story of a German-Jewish love that overcame the burden of the Holocaust.