Douglas Rushkoff thinks the Hillary Soprano ad fails because:

Hilary Clinton put herself in the role of Tony Soprano. He is a sociopath and a killer, willing to do anything for power. Why would a candidate present herself in such a role? […] Hilary and Bill Clinton have just made sure we equate Hilary’s ambitions and life with that of Tony Soprano (or, worse, Carmela – a woman who suffered her husband’s affairs in order to maintain the right to spend the capital he accumulates. Sound familiar?)

But the thing is… America LOVES Tony Soprano. Actually, America loves gangsters. Mostly fictional ones, sure. But also real ones, like John Gotti. They’re tough, ruthless, but for some reason… likable. Why wouldn’t the Clintons want to position themselves as a mob family? It’s a lot sexier than being a political dynasty. Plus, it sends a clear message to Clinton’s competitors.

Don’t me wrong, I think the ad sucks for a number of reasons. But association with the Sopranos isn’t one of them.