Once the tobacco is on the compound, the pouches wholesale for 50 books of stamps, or $300 each. Each pouch is then broken down into 80 to 100 tiny rollups that cost one book each, or six dollars. A $3 pouch of Bugler ends up retailing inside for about $600—a 20,000% markup.
The main complication for sellers comes if they need to convert stamps back into cash. While the 3-stampbook-per-prisoner rule is routinely flouted (imagine if you were only allowed to have three five-dollar bills at any given time), dealers, big willie prisoners or others looking to exchange often well-worn stamp books into dollars need an outside person to make a street-to-street transaction, with money wired to a family member or someone else on the outside in exchange for stamps trading hands on the inside.
With most of the money transactions taking place outside of the prison, it’s hard for investigators inside to track the transfers. And with only hundreds or thousands of dollars being moved at a time, it doesn’t attract the attention of outside law-enforcement authorities. “This one Sureño dude had shit on smash here. He literally made over $100,000 in a couple of years getting tobacco in like this. The homie came up. He was about his business,” the prisoner says.
“Most times the prison doesn’t sweat it because they are more worried about drugs and stabbings and the like. Keeping the violence to a minimum is their main concern. Tobacco is low on their agenda. A lot of guards don’t care about cigarettes anyhow. I mean, they smoke
Even when caught with 100 pouches of tobacco the infractions are minor. There is little deterrent to getting caught. “They might lock you in the hole or transfer you, but in the feds they can only write you a 300-series contraband shot if you get caught with smokes,” the prisoner says. “Compare that to a 100-series shot for drugs or stabbing someone.” Most prisons issue incident reports on a sliding scale from 100 series (highest severity) to 400 series (lowest severity). In essence, prisoners found holding tobacco, in any amount, get written up the same as if they get caught taking a tomato out of food service, which is also a contraband item.
“If you got several homeboys in place, someone on the outside to do the money transactions, some muscle to back your play and no problem with the minor consequences you can get rich off the cigarette hustle in no time flat,” the prisoner says. “For real, the guards and administration don’t sweat it. Just don’t front them off. If you keep it on the low, it’s all good. Dudes are supporting their families from their hustles in here. It’s crazy, but that’s just the way it is.”