This season of Mad Men was not much fun. Not that they ever really are — but this season was sad in a different way, a more anxiety-provoking way. We’re all sick of Don Draper by this point, sick to death of his compulsions, his past, his alternation between a fake detachment and a deep-seated panic that every once in a while issues in a bizarre hail Mary maneuver.
I’ve rewatched most of the series in the last month or so, and I can verify that Don has always basically been like this. When his identity was threatened in season 1, for example, he panicked and proposed running away to California, even before we knew what that meant. He’s always been cold and cruel, and he’s always “bought his own pitch” about childhood nostalgia. In short, he’s always been a man on the verge of falling apart. What made him fall apart so definitively this season, then?
The secret to his past success, such as it was, had been compartmentalization. Don was a serial adulterer who never slept with his secretary — and I’d propose that that’s not because he didn’t find them attractive or substantial enough (after all, he does sleep with the super-young jet setter and the flight attendant), but because he doesn’t want to shit where he eats. Work and personal life are separate. And weirdly, his personal life is also separate from his marriage, which is itself separate from his relationship to his children. Most separate of all, of course, is his actual real life as Dick Whitman.
The series is the story of the breakdown of that compartmentalization, as everything is collapsed into his work life — culminating in the disturbing scene in which Don can’t help but tell the Hershey’s representatives the decisive role that their product played in the life of an orphan whoreson.
The flashbacks in this season have elicited even more criticism than usual, and it’s true that they seem more “heavy-handed” than usual. I think it’s a mistake, however, to read the flashbacks as attempting to explain (or explain away) Don’s behavior. Throughout the series, they’ve had a very indirect and sometimes even puzzling relationship to the actions on which they supposedly comment. What is the relationship, for example, between the memory of the death of his father and the events leading up to the founding of the new agency in the final episode of season 3? Similarly, the relationship between Don’s actions in the recent finale and the scene where the preacher tries to set the whores free is indirect at best — why would that memory prompt him to beat up the preacher? Wouldn’t it make him more vulnerable to the preacher’s message, given that prostitutes are so clearly the only source of affection he received in those years?
I read this episode as a strange kind of clarification of the role of the flashbacks. They aren’t meant to explain his behavior, but to highlight its gratuitousness. He isn’t identifying with the confused, helpless orphan. He isn’t acting out the consequences of his premature sexual experience. He’s freely chosen to become the pimp. He acts as though he owns women, making thoughtless decisions that deeply effect all the important women in his life (ditching the account for which Joan had prostituted herself, bringing Peggy back into his sphere of influence and using her sexuality as part of his battle with Chaough, and literally calling Megan a whore for her soap opera sex scene). He takes advantage of Sylvia’s vulnerability after a fight with her husband to try to imprison her and turn her into the perfect whore — always available, with no purpose other than satisfying his needs.
We know that this is a choice because it wasn’t always so. Much of what redeemed him in past seasons was his attitudes toward women. While they weren’t what we would recognize as totally healthy today, they were sufficiently askew relative to his surroundings that they made him a strange kind of “feminist ally” at times — supporting Peggy, taking up with independent career women rather than vulnerable secretaries, etc. Megan provided him with a chance to crystalize all that, to unite the positive features of his relationships with women into one relationship. She was naturally motherly to his children, creative and ambitious like Peggy, genuinely caring and good like Anna Draper. Even though she was younger than him, she confronted him as a genuine partner — and he couldn’t do it. She really was his chance for redemption, and he threw it away.
Here we can recontextualize the Dante reference. Where he was in season 5 was purgatory. He had to suffer certain indignities (Megan’s various challenges to his traditional patriarchal authority) and deprivations (successfully going through a whole season without committing adultery) in order to be redeemed, but the option was there. In season 6, his life centers on the floor below his purgatorial apartment. He has descended into hell, and after we see his frequent recourse to the bottle, the bizarre ad in the season premiere that he presents as evocative of suicide seems more like an expression of the hope that we are at least dealing with the Greek Hades, where one gets to bathe in the River Lethe and forget. Unfortunately, he is in the good old Roman Catholic hell, where you can’t forget because your punishment fits the crime. He has to live out his decision to identify with the pimp by experiencing his workplace as structurally similar to a whorehouse — a place where power and money and intimacy overlap in the most disturbing and destructive possible ways.
What’s really interesting to me, though, is that he is finally deprived even of the scene of his suffering — Sterling Cooper and Partners refuses to be his personal whorehouse anymore, and it refuses above all to be the place where he tries to find a cheap redemption by once more identifying with that confused little boy. Someone else wants to use his hail Mary maneuver of moving to Los Angeles, and Don lets him, in a gesture that seems less redemptive than destructive when we realize that it marks the moment when Don has definitively turned Chaough into a version of his pathetic escapist self. Meanwhile, the women in his life kick away the ladder he provided them, realizing they can only “move forward” if he gets out of the way.
In this light, I prefer to read the final scene as radically ambiguous. We’ve seen him respond to that very same past in different ways throughout the series. More generally, what TV character is less constrained by circumstances than Don Draper? Who has reacted more creatively and surprisingly to moments of crisis?
Will he try to put himself forward as a victim? Will his reckoning prompt him to embrace empathy and genuine relationships? Will he try to reassert his dominance on the model of the pimp? We can’t know. Don has indeed descended into the abyss, but it cannot be an abyss of damnation or purgation — both of those options have come and gone. It is the abyss of freedom.
An und für sich 
I always assumed/suspected that the series would end with Don committing suicide, in the manner of the introductory titles… the abyss of freedom indeed.
I want to reclaim hell, really, like Blake does, as the source of creativity and power. Sometimes I feel Mad Men does reclaim hell: the most creative characters descend into the abyss and find what they need in the underworld, by sacrificing or being stripped of aspects of themselves.
And then at other times it seems to become a more conventional moral drama, where the abyss represents something entirely negative: ‘be good boys and girls or the abyss will get you’.
But after he commits suicide in the titles, he’s back sitting relaxed on the couch in his office, which is the end of the sequence… I always thought that signified his amazing resistance to change after successive crises. He gets out of a jam, promises to change, and then goes right back to his old ways. Like a cat with nine lives, but using them all up taunting the same pack of stray dogs.