In what ways do Trump's supporters see him risking his personal legacy or finances for the sake of his political goals?

I refuse to relate the win to improvement in his political aspirations. He is already POTUS, what would be next?

I would try to explain to anyone who listens, this is the greatest removal of medical insurance from the public in the history of the world. It will likely lead to poorer or lack of care and result in poor health and unnecessary deaths.