Originally Posted by
Upsetnneedhelp 
He says only the newer, younger inmates work while inside and that the older guys more or less look down upon that.
It sounds like he's trying to guilt trip you. i.e. other inmates will look down on him if he works. From what you have said so far he has told you that 'all the other inmates have one' and 'they will laugh/make fun of me if I do X'.
You obviously love him a great deal, but is it possible he is using that to manipulate you? Prison is an ideal time for him to focus on himself and to work through some issues. However, it is also a time when consequences play out. If you step in to provide him with distraction/entertainment and to get him out of having to work to achieve something, what will change? Surely he will only continue in his cycle of instant gratification - ask mum and get what he wants. Your boundaries are not only for you, but in this case, for his good too. If he wants a fancy state of the art t.v. then he should have to save up his snacks money and work and save that too.
Just my thoughts.