Sacred Heart Convalescent Home
You could argue Thomas Elliot never had much of a chance to be a good person, even when he was still Tommy. Still, some point between cutting his father’s brake lines and smothering his mother with a pillow, it seems like he leaned into it. When he became Hush, it was freefall.
Riddler essentially manipulated Hush into the masked crime circuit, so they’re generally on poor terms. Still, even those hang-ups must have been put aside for a chance to make Gotham, and by extension Batman, suffer. He throws you a crumpled ball of paper and skulks off... to plan.
Look at all those letters. Wonder where they go...