Keith Olbermann’s ‘Mad Men’ Theory On Don Draper Is Absolutely Bonkers

“It’s the waitress,” Keith Olbermann begins in a lengthy, six-page essay that he posted to Twitter over the weekend. After six pages and a lot of Shakespearean references, however, Olbermann’s bonkers theory about Mad Men and Don Draper can be summed up in four words: Diana kills Don Draper.


Granted, Olbermann hadn’t had the benefit of seeing last night’s episode before he wrote the piece, but it’s still on par with the D.B. Cooper theory in terms of pure crazy. You can read the entire thing by following Olbermann’s timeline, but these are the highlights of his theory:

1. Don Draper is a tragic hero of the Greek variety.

2. Greek tragedies do not succumb to last-minute twists.

3. Diana the waitress isn’t a last-minute twist/introduction because she’s “effectively a reincarnation of Rachel Menken” (no, she’s not!).

4. Diana has a history of lying, and there’s no reason to believe that her lies have stopped.

5. Don is awakening to his “tragic flaws” and is trying to correct them, but it’s too late.

6. Lou Avery took down Don Draper professionally, and now Diana will take him down personally. “Lou Avery is the storm that knocks the tree’s roots loose. Diana is the tornado that destroys it,” he writes.

7. Diana will be Don’s undoing.

“I don’t know if she kills him, or he kills himself, or they kill each other, or he jumps out of that collapsing life we see animated every Sunday night or he gets pushed out … Regardless, the collapse is underway and she has got to be the protagonist.”

8. How exactly might it end?

“If I had to put my money on a specific ending, I would assume Diana leaves Don in an impossible situation — running away or offing herself on their wedding day, or revealing his true identity, or just striking out in a blind rage when he doesn’t take no for an answer … I can’t imagine Weiner resisting the temptation to have Don die by defenestration, self- or otherwise, since we’ve been seeing that played out in the opening in every episode for eight friggin’ years.”

It is a fun theory, but I think it fails to take into account Matthew Weiner’s clear preferences for hope and optimism. I am 90 percent positive that Weiner wants a hopeful/happy ending. Mad Men is not a Shakespearean tragedy, and I don’t think that Don is a completely realized tragic hero. I think he does see the light before the end, and I don’t think we’ll be seeing anymore of Diana.

Plus, Don dying by defenestration would be too on the nose ever for Weiner.

Source: Twitter