should I contact my old boss, who’s in prison for a terrible crime?

Content warning for upsetting discussion of sexual abuse of children.

A reader writes:

I spent most of my 20s managing a business, eventually becoming more or less second-in-command. The owner was an older guy in his 60s. He was a bit of a grumpy guy and more conservative than me in many ways, but we overall got along very well. I found that he was generally a fair guy, and we bonded over a few shared interests. I wouldn’t call him a “friend,” but we had a good relationship.

He sold his business in 2020 (he was planning to retire that year anyway and the pandemic moved up the timeline a few months). He and I stayed in loose texting contact until I stopped hearing from him.

A few months ago, an old employee of mine reached out to me with some horrifying news: In 2023, our boss was sentenced to 20 years in federal prison for receipt of child pornography.

According to court filings, he had over 84,000 images of child sexual abuse material in his possession, which he amassed after trading images on Russian sites. Many of these images were violent and gruesome in ways that are too horrifying to recount, though he denies looking at the more horrific ones. He started amassing this collection not too long after he retired and moved in 2021. He was arrested later that year and eventually made a plea deal. He’ll be in prison until he’s in his 90s.

His defense team admitted that he has a “criminal interest” in boys between the ages of 11-14ish. This part horrified me, because many of our employees started out as high schoolers. Based on his testimony and my own experiences with him, I’m inclined to believe no human being who ever encountered him was ever in danger and he wasn’t even consciously aware of his attractions until he fell down this awful rabbit hole in his retirement. But I’ll never know, and I don’t know if he will either.

Even though he’s not accused of child abuse himself, the court did acknowledge that his interest in these images keeps the child sex abuse going, something even he agreed with during sentencing.

In the process of this, he got divorced, spent all his capital on a legal defense, lost all of his friends, and will very likely die in federal custody.

Despite the fact that he took part in a horrific trade, and that he had that criminal interest at all, I can’t help but feel sorry for him. It’s easy to see a story like this on the news, think “lock him up and throw away the key,” and move on. It’s harder when it’s someone you know. It’s all his own fault, but it’s sad knowing how he was saving up for retirement and built a business worth selling, only to lose everything. It’s sad knowing that his friends and most of his family have largely abandoned him. It’s sad knowing that if he’s lucky enough to survive prison, he’ll be in his 90s and flat broke.

With that, I come to my ask: should I reach out to him? I’m conflicted on this.

Part of me thinks he’d be embarrassed if I reached out, because only one of our coworkers was reached out to about this so I don’t think he knows I’d know. But part of me thinks about how a guy who did something horrible could probably use a little connection to the outside world, because he’s almost certainly lonely beyond belief. There’s also the fact that sexual interest in children is sometimes the result of abuse, which – and I don’t want to speculate more than this – means he might have been a victim himself.

I’m not asking for judgment on whether he’s a good or a bad person, because he undeniably did a bad thing. But people who do bad things, even horrific things, don’t necessarily deserve to lose all contact with humanity. I have no tolerance for people who produce those images, but I think that a lot of the people who trade and watch them are more sick than dangerous, if that makes any sense.

Should I let him live in ignorance of me knowing that I know, or should I reach out and try to form a human connection and alleviate some of that loneliness – without, obviously, excusing what he did?

This is not really a work question; this is a question about being a human around other humans, some of whom hurt others, and how we deal with people who have committed some of the worst harms against others.

I can’t tell you what you should do.

I am going to point out that there’s a lot of minimizing language in your letter about a man who found sexual gratification by watching children being abused, thousands of them, perhaps violently, and who actively helped to create a market for that abuse.

Is he still a human who could use a connection to the outside world? Yes. Might he have been a victim himself? Maybe. Did he repeatedly choose to do something that causes severe and lasting harm to kids? Yes.

There are people who feel called to work with people who have committed some of the worst crimes possible, to find their humanity and connect with it. Maybe you’re one of them.

But I would get really clear in your head about what’s motivating you and whether you could explain it to someone who’s been a victim of this type of abuse and still come away feeling confident in your stance. If you can, there’s your answer. And if you can’t, I think that’s an answer too.

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