top of page

Tony Gentry

Mailing Books to Prison

Updated: May 17

I have a friend who, through some combination of depression, online curiosity, and bad choices, has found himself in a low security federal prison on a 7-10 year bid. He’s past the halfway point now, on the downslope to reentry, and just as I have since he got there, twice a month I send him a short stack of paperback books. Which is pretty much the only thing anyone is allowed to mail a federal prisoner. I keep a list of these books, so I won’t send the same one twice, a total of over 400 so far. He says the library at his prison is pretty good, but appreciates the packages, because the books I send haven’t been dog-eared or dropped on the disgusting toilet floor yet, and sometimes he can barter them for instant coffee or a favor, or just hand them over to the library when he’s done.

By all accounts, he’s a model prisoner. Stays out of trouble, helps out other guys with letters home. Served as commissioner of the prison baseball league. Even organized a Spanish-English course that he and a Hispanic prisoner taught together. But the prison administrators don’t understand his benevolence, fear that he may gain some influence, and they punish him for his efforts. Ordered him to give up the language course, busting him to janitorial duty. They even called him on the carpet over the books I send. Several times the packages disappeared, or they came back to me. Under the current arrangement, I can only send two or three at a time and they must be wrapped in white butcher paper. He says when a package arrives, a guard tears open the wrapper, thumbs through the books and then tosses them out on the floor as if they’re garbage, so my friend has to pick them up. I’ve asked him if he wants me to stop, but he says no. He says they offer him the one escape he has, the respite provided — even in a noisy, smelly, zero privacy environment — by a story on a page.

Where do I get these books? Well, I buy some new, send some from my own over-stocked collection (having decided that I’ll only hang on to my few first editions and any rare books not likely to be in the VCU library), but most of them I get from a nearby Goodwill warehouse at 25-cents each. Visiting this warehouse has become a guilty pleasure, since I can’t seem to leave the place without a dozen or more books, until this winnowing I’ve been attempting has begun to run in reverse. The attic of our house is at risk of sagging from the boxes of books stored there. My wife says if my friend were doing a 25-to-life bid, I’d still never run out of books to send him. I can’t help it, though. One of my favorite things, across my whole life, really, is discovering a new book. I still remember coming across Richard Price’s dazzling first novel The Wanderers atop a garbage can on 6th Street in the East Village. Had never heard of the guy. But wow.

Sometimes at Goodwill it’s pretty clear that a whole collection has been dumped at once. One day I came home with a half dozen zen classics, another time it was travel books ranging from Muir to McPhee, another time a whole bookshelf on Native Americans. I find review copies of novels that will compete for the Pulitzer before they hit the shelves. A lot of them are in good shape. Walking out with $3 worth of books (that’s a dozen!), I feel like a rich man.

Of course, I’m not the only one who has discovered this treasure trove. One day I found a man filling up three shopping carts with books (slim pickings for me that day). He said he boxes them up and sends them to a school in Africa. There’s this one guy who cut a deal with Goodwill to buy whole pallets of books sight unseen, and a crew that descends like locusts, combing through the bins with ruthless speed for whatever they can sell online. So, sometimes, I find nothing of interest. But when I do, woo-hoo! I haul them up to the attic, read them as fast as I can, send 2-3 at a time off to my buddy, drop the children’s books at an inner city elementary school, and recirculate the rest to the local library, where likely as not they end up eventually back at Goodwill.

It’s an inexpensive vice, is how I figure it. And like my friend says, when he’s finally released from his no-Internet/sports tv-only imprisonment, he’ll be better read than most professors. Will that in any way assist his transition back to the real world? Who knows? If it helps him and his cellies stay sane for now, that’s enough, right? But I’ve got to do something about that attic.

(By the way, I keep a blog for my friend, too. He hasn’t posted in a while, since breaking his writing hand playing basketball, but here’s the link:

PS – I try to send books that I love, classics and those that deserve to be. If you’d like to see the list, put your email in a comment and I’ll send it to you.

0 views0 comments

Recent Posts

See All


bottom of page