Boofing Knowledge

Entering the prison system—or having a loved one who does—introduces you to a whole new world of vocabulary you never expected to learn. You encounter people from walks of life so different from your own that you almost feel like you’re in a bizarre, twisted reality show. My time at Riker's Island, the notorious prison known for its violence, neglect, and all-around human degradation, was no exception.

I was a fresh fish, trying to keep to myself, my nose buried in any book I could get my hands on. At the time, I was reading Long Walk to Freedom, Nelson Mandela’s autobiography—a man who spent 27 years in prison fighting for racial equality in my homeland, South Africa. One of his quotes struck me deeply: “You don’t truly know the people of a nation until you know those who are in prison.”

Before my own incarceration, I naively viewed prisoners as just criminals. But that was before I really understood how the so-call “justice” system works and how easily freedom can be taken for granted, until it’s snatched away, leaving you in the dark—both figuratively and, often, literally.

But back to Riker's and my bunkmate, a guy named Smiley. He was in his early 40s, and his life story was the kind of tragic that made my problems seem small. Smiley wasn’t much to look at—he reminded me of Gollum from Lord of the Rings, only with even worse teeth. Hard to imagine, right? But that was Smiley, always flashing a grin that could give nightmares to a dental hygienist. That’s actually how he got his nickname—his horrific, cavernous smile was permanently plastered across his face, despite the tragic life that led him there. 

Smiley wasn’t much to look at, but he had a surprisingly upbeat attitude for a guy who’d been manipulated into a life of crime and was now staring down a five-year prison sentence. Over time, we started to share stories. He told me about his childhood, and how, when he was just a kid, he’d been playing with his uncle’s gun with a friend. His buddy thought it would be funny to play cops and robbers, holding the gun to the back of Smiley’s head. “Freeze! You’re under arrest! Get down on your knees” his friend shouted. Then, he got down on his knees and boom—the gun went off.

The bullet passed clean through Smiley’s skull, shot out through his closed mouth, and shattered his teeth into a mangled mess. I looked at him, jaw on the floor, as he knelt down to show me the bullet hole. I couldn’t believe he was still alive, let alone standing there with no brain damage—at least, so he claimed.

As we exchanged stories, I started to realize how little I knew about life inside prison. Smiley would drop prison slang left and right, and I’d have to stop him mid-sentence. “Wait, what’s ‘capping’?” I’d ask. “What’s ‘boofing’?”

That last one—“boofing”—really threw me for a loop. Smiley saw the blank look on my face and tried to clarify: “You know, ‘whooping,’ ‘keistering.’” Blank stare again from me. Finally, with a wicked grin, he said, “Your prison wallet,” and pointed to his backside.

“Ohhh,” I said, my stomach curdled as I realized what he meant. Boofing, as it turns out, is the art of smuggling contraband into prison by, well, shoving it up your arse. And let me tell you, almost everything at Riker's—cigarettes, drugs, you name it—came through someone’s “prison wallet.” The thought made me gag, but I was also weirdly fascinated by the ingenuity involved.

Smiley was just as curious about my life as I was about his. He couldn’t believe I’d come to America homeless and somehow clawed my way to financial independence making my first million in my late 20's. We swapped stories like old war buddies, and I gave him my top three books that had changed my life. Smiley scribbled down the titles with the enthusiasm of a kid writing his Christmas wish list.

The next day, Smiley got the call—he was being transferred upstate. He interrupted me mid-phone call, grinning with his signature ghastly smile, and said, “I’m outta here. Thanks for everything. You really changed my mindset. I’m taking those book titles with me—they’re the only thing I’m bringing upstate.”

Confused, I asked, “How? You can’t take anything with you when you go upstate.”

With that, Smiley flashed me the gnarliest grin, his broken teeth jutting out like jagged rocks, and shouted, “I boofed it!”

Once again, I was left in shock, realizing just how backward and bizarre prison life can be. Normally, we absorb knowledge from the top down—into our brains, from our heads. But here was Smiley, taking in wisdom from the bottom up—literally.

Curious about the books Smiley boofed? Email the90daycoach@gmail.com with the subject line “Boof Me Knowledge” to receive the free PDF.

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