Bloomberg may have gotten himself into hot water with that stunt of paying off the debts of felons so they can vote. He may be breaking the law by offering somethjng of value in exchange for a vote for a certain candidate.
Snopes says it’s true, and at the bottom of the page they have the source documentation from the Florida Attorney General listing the possible violations of Florida law.
I believe the question of criminality would revolve around whether he did this with the expectation of the voters voting one way. And apparently those felons vote 92% Democrat, and there is an E-mail from Bloomberg or one of his aides that points this out.