They have a really good point, and it’s super clear neither of you have been to prison. Money in commissary at one place not following when you get transferred and money staying with the prison when you get released are both real problems. More than ~$1k on your books really isn’t an advantage, can’t buy much past snacks/hygiene/sometimes very limited entertainment stuff anyways. Withholding entirely until he’s out is pretty lame though, being able to buy a toothbrush and a tiny bag of chips for $25 is the least he deserves. I’ve never dealt with someone famous being locked up, but usually you try to get money to someone outside they trust who can pay lawyers/put it on books as needed