You guys are delusional about how jails work. It's literally set up as a way to pull money from people. There are literally poor people jails that let you have a tablet with movies/games at extremely expensive rates (you just need someone to put the money in your account for you). You can buy a personal TV in a lot of jails/prisons. You can buy namebrand soap/toothpaste/shampoo.

It's insane to think he is going to be able to sneak the cash to the guard somehow. Like how exactly do you wire this cash to a random guard over a phonecall with a friend? It's like planning to bribe the guard with drugs/women when the person doesn't even know any drug dealers or prostitutes to begin with. Laundering cash is one of the hardest parts of crime.