He is in the construction business. Home base New York.
There is no way he could be successful like that without dealing with certain and many entities.
ahem....
Yes, I would bet he has dealt with all types, including the mob. He seems to come out on top or reach an agreement that benefits him. Seems like that would put him in good stead in negotiating with the world leaders, many who resemble gangsters and most of our current politicians who have much less honor than the mob.