The author of the Gawker essay doesn't miss the point of the show, exactly, so much as he fails to see the big picture. Mad Men is sexy, yes, and its world is oozing with masculine entitlement. And, unavoidably, it makes that masculism sexy, too.
But that's not all that it's doing, because even when the show is endorsing a character, a philosophy, or a behavior, (think: Peggy) it's also always ambivalent about them (think: the final shot of Peggy in this season). As much as it might celebrate machismo, it undercuts and emasculates those same masculine men even more frequently:
- Pete Campbell cheats on his wife and is sadder for it
- he becomes more successful and confident in business, and it leads to an impromptu boxing match that he loses decisively
- Don appears to realize that his happiness always comes at the expense of the happiness of those around him, and vice versa
- Roger's loss of business acumen and relevance coincides with his LSD-fueled realization that other people have feelings, which seems to say a lot about how business works.
It's a tragedy, but a classical one. I suppose that it's also tragic in the more contemporary sense - we do feel sympathy for Roger and Don (and even for Pete, sometimes) when things go wrong. But we're also given the sense that they're all their own worst enemies. It's their hubris, more than anything else, that's responsible for their failures and the decline of their world that we, the viewers, know is inevitable. Because they have no idea that another world is possible, and that men like them won't live forever. We, on the other hand, know that the clock is ticking. And that's why the show isn't an endorsement or celebration - it's a cautionary tale.