The man Dick Whitman turned himself into is a master of the universe, capable of playing all the angles and finding a way to win the unlikeliest of victories. But here, we see other men sitting in Don's chair, putting him ill at ease and telling him how his life is going to be. Connie makes it clear that, however they bonded at the country club, he's going to dictate the terms of this relationship. And Bert Cooper turns out not to be the doddering eccentric we've taken him for, but an absolute killer. He's had the Dick Whitman card in his pocket since the end of season one, but he's declined to play it until now, going straight at Don with it, yet being elegant enough to phrase his attack in an oblique way. (He paraphrases a line he used on Don in last season's "The Gold Violin" about how he knows a little about him, then asks, "After all, when it comes down to it, who's really signing the contract, anyway?")
I think the key moment of the entire episode -- right up there with the moment in which Don signed the contract -- was when he looked into the mirror in that motel room and realized he'd been played. He'd been rolled by a couple of kids. And hell, maybe in his own self-destructive way, he'd realized from the start that was possible. But it almost didn't matter. He just wanted out.
Where "out" led was to this: The hustler got hustled. Don/Dick had to be as shrewd and brutal as those kids in order to get where he's gotten (and frankly he was lucky that the kids didn't take his new Caddy). But as his old man (i.e., his subconscious) pointed out, he had grown soft. A life lived on his terms has made him, in some ways, weak and vulnerable. It turned him into the kind of suburbanite who gets preyed on by streetwise types. …
Don wanted to be the alpha male who brought in a big account and yet could keep wielding power on his own terms. He was told no, which is not something that frequently happens to him. Don was the star of Sterling Cooper, but he could no longer shine.
But nobody denies Connie or Bert. Two sun kings who used their power and schooled Don about who's in control.
Isn't that the American dream, after all? We like to see ourselves as independent, headstrong, deeply unique individuals, paving our own paths through the wilds of contemporary life. We so easily forget that almost every decision we make, from whether or not we breast feed our babies, work overtime, sleep more than six hours a night, exercise, visit the doctor, vote, do drugs, drink, stay married, all of it, springs from the common, accepted attitudes of the times. The beliefs we hold most sacred, the ideas that define our identities, more often than not boil down to trends. It might take a few decades, but one day we inevitably wake up and notice that a big percentage of the individuals in our demographic were also smoking, dabbling in Buddhism, using formula, spanking their kids with a wooden spoon, getting divorced in middle age, reading Dr. Spock, becoming vegan, you name it. The very choices that feel fundamental to us are the ones that look almost hilariously cliché and goofy in retrospect.