I would give a nod to Anita in Philly as well, though I think UncleNicky (was it New York?) and MrEvilman (maybe New Orleans?) should get credit as well, considering their empires were built in a world where bodyguards were limited.

Not quite True. MrEvilMan had a number of Bodyguards, bought with money he earned by exploiting a bug at the time, so you can hardly include him in this.

UncleNicky i'll give you, though. UN were feared and respected by many, though my bloodline was on the opposite side and often fought with the UN, they always respected them and it made the fight much more enjoyable. The likes of UncleNicky, Kev and Kes are well remembered even to this day for being members of UN as they often still carry the little 1041 tags.

TylerDurden's Delaware hands down. Sure he is constantly being wiped, but I mean, come on, who else can keep coming back over and over with hundreds of goons at his whim?