I don't think he's having trouble with the math. He understands what's at stake. The plan is to set them back so far, and to scare them so much they'll think very long & hard before they do it again... which they will.
The question is, how hard do you redpill people? The answer is simple; hard enough. Losing some institutions has to be worth it in most of these cases. I know I'd rather set us back a generation, if it teaches us a lesson for 200 years.