I originally had this as part of a reply to gmcz's "Aftermath of Bobby's First Kill" thread but thought better of it. This post is really about Tony, not about the possible legal consequences of the hit and not about its effect on Bobby.
When Bobby confirms that he's never "popped his cherry", several things are notable about Tony's initial (pre-fight) reaction. He uttered his Italian "a salude"(sp?), a seemingly very genuine "good for you".
The wording was very reminiscent of The Happy Wanderer, when Tony was so angry at the world -- and particularly at people who were content or otherwise unburdened by the kind of crap that burdened him -- that he literally was driven batty at the sight of them. He reported wanting to pound Melfi's face with a brick until it was hamburger (ouch, LMAO!) and wanting to pummel to death anyone "with a clear head", anyone happy enough to whistle. He acknowledged that he SHOULD be glad for that person, "a salude", but that he "couldn't stop feeling like a fucking loser".
Obviously, self-loathing was the key to his jealous anger at the "happy wanderers" and has remained the key to his recurrent efforts over the years to sabotage anyone close to him that tried to improve him/herself, whether it was Chris and his sobriety, Tony B's efforts to go straight, or Janice and her anger management. He's been equally guilty of trying to corrupt people of comparitively good character, be it Melfi, Artie, or the black cop that he got reassigned and tried to bribe -- twice.
Right after offering his "a salude" to Bobby, Tony continues "it (murder) is a big fat pain in the balls." While Bobby, a virgin to this crime of crimes, immediately took the remark in the context of self-preservation and legal consequences ("especially with this DNA evidence"), Tony -- a pensive, remote, and pained expression on his face -- was unmistakably talking about the emotional/psychological/moral consequences of it. This is significant, I think, because it's the closest Tony has come to admitting that the murders he's committed, far from being dismissible as merely part of a "soldier's code" and the mutually agreeable price to be paid for mob involvement, weigh heavily on his conscience. And we see, through Bobby's struggle at the end of the episode, that once a trigger is pulled by anyone with a spark of decency, it changes the shooter forever.
If it turns out that the "therapy breakthrough" touted in HBO promotional material before this season is truly profound and amounts to a naked confession and moral self-examination in Melfi's office, I see this little remark as the precursor, the signal that it's coming.
And to wring out every last ounce of symbolism, in true Chase Lounge style:icon_wink:, I find it interesting that Tony used the expression "a big, fat pain in the balls." I won't recapitulate yet again the recurrent references to castration in the series or the implications of the name "Soprano" itself, but recall that Tony's tachichardia and flatlining in Mayham was accompanied (if not caused) by Paulie's relentlessly graphic account of a serious testicular injury and concurrent cursing of a mob rat. Recall also that most of the conflict last year between Tony and AJ involved Tony's demand that AJ grow up and become "a man" while AJ was and is frightened at what it means to be a "man" in the Soprano family. Tony tells Melfi that if he'd whipped the crap out of AJ like his father had him, AJ "might have grown up with some balls". It was only the most recent of a plethora of scenarios throughout the series linking manhood to the aptitude for physical brutality and violence.
It follows that if Tony is lamenting the toll his violent history is exacting on his conscience, his subconscious might well lead him to describe it as a pain owing to his "manhood", felt in the area that embodies it. It also follows that his nastiest, coldest act of revenge against a relatively "happy wanderer" like Bobby would be to subject him to the same burden under which he labors. Setting Bobby up for the Canadian hit doesn't just feel like vindictiveness or a test of Bobby's loyalty or fitness to lead a violent criminal enterprise, though it is certainly the former and possibly the latter. It also feels like the beginning of a confession.
Tony, his spirits crushed after b-lining to the fridge first thing in the morning: "Who ate the last piece of cake?"