Popular media like to depict gangsters not having to pay the bill. But in reality they only do that in restaurant/ clubs owned by someone connected & rarely ever in "public" or shall we say "citizens" places... Unless u were Greg Depalma

ie Gaspipe spent huge amounts dining out. Scarfo according to Nicky crow always picked up the tab

Not sure how accurate Joe Watts picking all of Gotti's tab was... Gotti mostly ate at Da Noi which was his own place and had a table at Raoul's.... Drank at Regines... I wouldn't want to pick up his tabs

So is there any formality ie the boss pays or an underlying pays for the boss within LCN?
I've grown up around a lot of Chinese & viet gangsters, the boss ALWAYS pays. It's a respect thing- the elder pays. If an underling pays it can be a sign of weakness. Unless it was a birthday where everyone chips in that's different