Two that I know of - my father and my great grandfather. My father was an outlaw biker, and by the time he died he had a pretty long criminal record stretching over probably 50 years, mostly petty stuff but with at least one serious conviction that I know of and possibly others that I don't (he didn't exactly keep me posted on such things).
I don't know the specifics of what my g. grandfather did because my grandfather didn't like to talk about him, but I know that something happened when he was in the service before/during WWI that led to him fleeing back to the "old country" (Ireland; my family came over during the Famine) for several years, where he met and married my g. grandmother before coming back to N. America via Canada, using a different spelling of the family name. He eventually abandoned the family, after they moved back to the States, and family legend has it that the reason he left was because his past was catching up to him.