Well philly did 20 years in the can that would earn him a lot of respect in the lcn, and even phil points out in the show that tonys never done real time. I think that phil was first introduced i thought he seemed like the most old school type in the show but i think towards the end they started to get a little carried away with his character like after doc santoro got killed and phil became the offcial boss they had that ridicoulous party/ceremony for him, then he decides to go to war over one little dispute. I dont think either of them is truly old school which was one of the big themes of the show, showing how the modern day mafia has lost its class and its no longer like the godfather, to show how theyre not to be romantisized but that theyre just criminals.