When did you lose respect for Tony?

Like all of us, we've watched the show multiple times. We all understand it's intent. It doesn't glamorize organized crime, it kind of pokes fun at it. I can't think of a single character I don't like. They all have amazing story arcs (Where's my arc Paulie?).

I manuged to figure out when I lost respect for Tony. At first I thought it was when he finished off Christopher after the accident. Getting rid of a headache seemed appropriate. However I changed it to when he went to Paulie's apartment. He found the portrait Paulie had rescued from the dumpster, gave him shit then took it. For all of Paulie's issues he loved Tony...I know he was fickle....but Tony could've used this as a moment to really ingratiate Paulie to him. Paulie had reached out to Johnny for reasons we all know, Tony knew that of course. I really think he missed a chance to grow as a boss and a friend, but he couldn't help being who he is.

Thoughts?