I get to decide who I associate with. I'm flattered that you believe I have the power to dictate the direction of a convict's entire life, but I'm afraid that's not the case.
If you are offering some product or service to customers you are not 100% free to decide if the customer deserves your service. Otherwise you could refuse to service black people or gay people or atheists or ex convicts or whatever group gets piled up on by the society at the moment.
Privately you should have the full freedom to choose who you associate with though.
would you vote for/support laws that would extend punishments? you personally don't have the power to 'dictate' on your own, but we all vote in people who nominally represent our views on these sorts of topics.
So you get to decide if he has to pay eternally.