I used to volunteer at Prisons. Some of these older guys– they’ve been there for decades. Their family members are either dead or estranged. They don’t really know what a computer or the Internet is, and will have a terrible time finding any sort of job. Their siblings etc might not care about them, or actively hate them. The only people they know on the outside might be their drug kakis, or gang kakis, and even those are usually gone. Some of them openly say, when I get out I’m just going to do drugs again and come back here where my friends are.
EDIT: Noticed a few well-intentioned comments saying things like “free food, free housing” – TECHNICALLY true but doesn’t capture the whole picture. It’s not that they learn to love the prison environment, it’s that the environment outside of it is especially harsh to them in ways we can’t even begin to imagine. We all have things we take for granted that help us survive– jobs, family, friends, savings, etc. These guys – and I’m guessing this is definitely the case for the 60yo dude in the article– have none of that.