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Drew P. Weiner
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Yes, it isn't that he's being driven by a gambling addiction as much as he's being driven by trying to break his streak of "bad luck".

I think he's more upset about the loss of that 200K and/or that Hesh didn't really seem to care that he bothered bringing it.

I think he's more upset about the loss of that 200K and/or that Hesh didn't really seem to care that he bothered bringing it.

This one and "Christopher"…maybe D-Girl too, although that one doesn't irk me as much.

This one and "Christopher"…maybe D-Girl too, although that one doesn't irk me as much.

Cutting every corner, using cheap lumber to save money and "leaning on" the building inspector to overlook it, all of it on Tony's dime as she pats herself on the back for "her" business "success". She's as loathsome as he is.

Cutting every corner, using cheap lumber to save money and "leaning on" the building inspector to overlook it, all of it on Tony's dime as she pats herself on the back for "her" business "success". She's as loathsome as he is.

And when Tony was trying to talk to Vito Jr…."your father and I were friends."

And when Tony was trying to talk to Vito Jr…."your father and I were friends."

"Big Boss Man". Love how Phil is just basking in the accolades of finally being the boss.

"Big Boss Man". Love how Phil is just basking in the accolades of finally being the boss.

He also knows that a) Tony is having cash flow issues and b) his lifestyle basically chews through cash at an enormous rate.

He also knows that a) Tony is having cash flow issues and b) his lifestyle basically chews through cash at an enormous rate.

Tough not to feel bad for poor, poor Hesh in this one. Tony was just plain cruel to the guy, who, after all, just lent him 200K which he gambled into nothing. Another good example of what Christopher pointed out a few seasons ago…"you preach all this wiseguy stuff, but the only ones who have to play by the rules are

Tough not to feel bad for poor, poor Hesh in this one. Tony was just plain cruel to the guy, who, after all, just lent him 200K which he gambled into nothing. Another good example of what Christopher pointed out a few seasons ago…"you preach all this wiseguy stuff, but the only ones who have to play by the rules are

Yup, there was the Frelinghuysen Ave. property and the HUD scam, both of which got back to Carmine and Sack. Funny part is that Paulie just let that info slip while he was whining to Johnny about things in general, as opposed to the Ginny joke which he deliberately used to stir things up. 

Yup, there was the Frelinghuysen Ave. property and the HUD scam, both of which got back to Carmine and Sack. Funny part is that Paulie just let that info slip while he was whining to Johnny about things in general, as opposed to the Ginny joke which he deliberately used to stir things up. 

Tony was just plain goading him on at that point, showing more of that cruel streak of his that grew even more nasty as the season went on.

Tony was just plain goading him on at that point, showing more of that cruel streak of his that grew even more nasty as the season went on.

That look on Tony's face when he realizes he can't bring himself to kill Paulie…it's like he's disgusted by himself for not being able to do it AND for even seriously considering it. Awesome scene.