I don't see what could possibly be reprehensible about making a lot of money, in and of itself.
All welfare recipients do it intentionally, and many of them are using the system appropriately and in good faith, so there's nothing reprehensible about that either, in and of itself.
In order to make a clear judgment about either of these things, I'd need to be presented with an individual situation. How is the millionaire making their money? What sort of situation is the welfare recipient in?
I voted for the welfare recipient, simply because at best (it's being used as intended and in good faith) it still indicates that something bad has happened in someone's life, and at worst it's being abused by someone who is manipulating the system. It's never good news that someone is on welfare, even if they have a very good reason. It always sucks to be in such dire straights that you would need it.