Love Behind Bars: On the Complicated World of Incarcerated Romance

Elizabeth Greenwood Avatar

Of all the correspondents I’ve had in my life, Sam Israel has been among the most consistent. Sam was serving a twenty-two-year sentence in federal prison for fraud when we met. He’d been running a Ponzi scheme out of a hedge fund that began with him stealing hundreds of millions of dollars from investors and ended with him staging his suicide on the Bear Mountain Bridge in 2008. His was the largest Ponzi scheme in American history until Bernie Madoff’s malfeasance came to light a few months later

I initially interviewed Sam for my book Playing Dead: A Journey Through the World of Death Fraud because he had faked his death. Investigators claimed not to believe the note he left, which read “suicide is painless,” on his parked GMC Envoy on the bridge. But they didn’t catch up with him until he turned himself in. He was hiding out in an RV at a campground in Massachusetts when he saw himself on an episode of America’s Most Wanted, a few weeks after his faked death. Over the prison email system CorrLinks and phone calls, we discussed at length the psychology and logistics behind the decision to stage his death. But that was just the beginning.

Sam and I continued to exchange emails and phone calls, talking about life, what he’d learned from his mistakes, and nearly everything in between. As I was putting the finishing touches on Playing Dead, Sam mentioned that an episode of American Greed on his story had recently aired. And he started getting mail, letters from people (mostly women) he’d never met, but who were interested in him.

I was totally fascinated. Of course, I’d heard of this: the perennial tabloid grotesquerie of women writing serial killers, proclaiming their love and avowing his innocence. No offense to Sam, but he was broke, disgraced, and unlikely to be getting out of prison any time soon. So what did these women want?

I began digging around, and what I found with this phenomenon was similar to what I found in the world of death fraud: what sounds completely crazy from the outside possesses, curiously, its own internal logic. When I examined faking death, I found quite a bit to learn about what it means to live a life, and when I looked more closely at prison relationships I found a world and ecosystem unto itself, with a lot to teach us about what a relationship is.

The first breakthrough in my reporting was finding the organization Strong Prison Wives and Families, and its founder Ro, and her best friend Jo. (Ro and Jo, you cannot make these things up.) Ro founded the organization because her fiancé was serving a 213-year sentence under mandatory minimum sentencing guidelines, and she wanted to create a space for women who are supporting a loved one in prison to exchange tips and information, and more than anything, express joy about their relationships, which are often judged harshly by friends and family. Jo was a leader in the organization, sharing candidly about the challenges and triumphs of falling in love a man who was in prison across the country serving a sentence for attempting to murder his last girlfriend.

I met the two friends in person for the first time for lunch at Ruby Tuesday in the Deptford Mall in New Jersey. Jo needed Ro’s help with a task only another prison wife could understand: picking out outfits for prison visiting that are sexy enough to hold your man’s attention yet conservative enough to get past security. And Jo needed a bunch of outfits, as she was heading to the maximum-security prison in Oregon where Benny was confined to marry him and stay for a week of visiting. It would be the fourth time she and Benny had met face-to-face.

These women blew me away. Over salads and iced teas, they broke down so many challenges, things I never would have imagined. At the facility where Ro visited Adam, the visiting period is six hours and they cannot bring anything inside the room. She and other women had to figure out what to do when they had their periods and couldn’t bring in tampons.

They explained to me the pecking order among prison wives: couples who were in a relationship before incarceration are at the top. Those who knew each other before one went to prison—as classmates or co-workers, with some kind of free-world experience— and then reconnected once one went away are in the middle. And those, like Jo and Benny, who met while incarcerated, or “MWI,” are at the very bottom. They broke down the thousands of dollars they spend a month, on prison phone calls, emails, and visits. They told me about the friendships and family members they lost because of the stigma of loving someone in prison.

It was inspiring to meet these women, who are intelligent, successful, funny, and gorgeous, living life on their own terms. They talked about experiencing love like never before. But I constantly had to wonder: was the juice worth the squeeze? Because the squeeze was big, financially, emotionally, and personally.

A few weeks later after meeting Ro and Jo at the mall, I was walking Jo down the aisle of a maximum-security prison to marry Benny. What laid ahead for them was something beyond anything I could have imagined when I began writing with Sam, and likely far more than they themselves could ever have conjured. I followed the ups and downs of their relationship through Benny’s homecoming in 2020, and remain friends with Jo to this day. I’m never not inspired by her tough and tender outlook on life.

After serving 15 years, Sam got out under the two-thirds elderly offender provision of the CARES act earlier this year, and we still speak often. Though now it’s through texting instead of CorrLinks. My relationship with him is a reminder that asking questions and being present for people can bring you and into worlds most of us never glimpse.

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Elizabeth Greenwood Avatar

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