Mostly, I had it in my head that in the Benz, Howard totally offered Obadiah sexual favors in exchange for Obie leaving Tony the hell alone. And Obadiah agrees, of course he agrees, because he's missed the good old days so very much, and really, what are friends for. And then he goes to Tony and says "your father doesn't want us spending time together," says "I don't know, Tony," says "we'll have to be careful," says "your father is a sorry cocksucker" because, it's true, Tony is much better at this, and also, because Tony just thinks he means that Howard is a bastard. Obadiah likes getting away with things, is basically what it comes down to.
Re: SORRY SORRY NOT MY TURN BUT I WAS OVERCOME BY OBADIAH'S COCK.
Mostly, I had it in my head that in the Benz, Howard totally offered Obadiah sexual favors in exchange for Obie leaving Tony the hell alone. And Obadiah agrees, of course he agrees, because he's missed the good old days so very much, and really, what are friends for. And then he goes to Tony and says "your father doesn't want us spending time together," says "I don't know, Tony," says "we'll have to be careful," says "your father is a sorry cocksucker" because, it's true, Tony is much better at this, and also, because Tony just thinks he means that Howard is a bastard. Obadiah likes getting away with things, is basically what it comes down to.