As worded, this isn’t a very fair rule-of-thumb. Plenty of people “do the crime and do the time” and shouldn’t have their pasts haunting them like an albatross.
I think “history with the law” could be replaced with “currently in trouble with the law” and be a bit more fair. But there’s still the “innocent until proven guilty part”
(To be clear, Michael sounds like a complete asshat)