James Khubiar writes that the Members Only jacket signifies that the lone diner was a hitman. More importantly, though, season over season, the motive is set:
- a history of straddling the line between the New York and New Jersey families;
- suspicions that Tony works with the FBI;
- a number of grievances about decisions and leadership.
Paulie cut a deal with New York where he would arrange the assassination of Tony and declare himself the new boss of the DiMeo family. New York would back it with their muscle and influence to make sure Paulie’s coup is seen as legitimate within the remaining Soprano family and the Five Families. In return, they would have a peaceful and harmonious relationship with New Jersey, something they had not had in years. This kind of relationship was especially necessary for Lupertazzi Family considering they had been in the middle of a two year civil war and was about to have their fourth boss in less than three years (Carmine, Johnny, Phil, and whoever would replace Phil). Beyond that, a boss turned state’s witness is an absolute nightmare scenario so Tony would need to be eliminated for the benefit of New York.