I dunno man, personally I try to avoid living my life by walking right up to the edge of what's legal, and I don't admire or respect that trait in others either.
https://en.wikipedia.org/wiki/Citizens_United_v._FEC
Its the ruling that would predictably lead to outright bribery of Congress, but SCOTUS thought it would violate the rights of money?!?!, so they allowed literal bribery of congress.