I would say Carmine Lombardozzi. I remember reading somewhere that as he got older he was the biggest earner alive. There could have been someone before him or after him who earned more, but i don't know. I wouldn't really count bosses like Capone since that don't necessarily earn anything themselves since they mostly oversee others.
Among other things,i believe Lombardozzi was one of the first guys to realize the full potential of the Stock Market as a new source of income for the Family. Nicknamed The Doctor,he was a ferocious money machine. You're right about Capone and other bosses. I was responding to income amounts,but the topic was biggest income generators,not recipients.
