Wanted to post this BEFORE the penultimate episode of Mad Men airs on Sunday, May 10th (which of course I’ll be recapping for HNTP).

Mad Men is the biggest tease on television. It frustrates us by throwing out hints about where things are going, and then not going there. This constant business of creating expectation and then subverting it is at the same time awesome. It’s sweet and sour. It’s slap and tickle. It’s like the entire series is one long Pine Barrens episode. Hell, many of us are still waiting for the return of Salvatore Romano. There’s no question that the showrunner, Matt Wiener, is aware of the various theories and enjoys misdirecting us and/or acknowledging our speculations.

The Draper icon falling through the air in the opening credits has led to speculation that sooner or later someone – most likely Don though for a while it looked like it would be Pete – was going to go out a window or fall off a terrace. But now Don works in an office where the windows don’t open, and he’s sold the apartment with the terrace. It’s not going to happen. We can also pretty much rule out Megan’s either being Sharon Tate or being killed in a Sharon Tate like manor. It’s 1970 and the Manson family has been mentioned, so Megan’s Tate-identical tee-shirt, and comments about her isolated Valley home were all part of an elaborate con. We know that Don is not DB Cooper though the show was (probably) not responsible for that one. Wiener even referenced the rumor on Conan. While he dismissed it, Don’s fate may yet

be Cooper-like. That is, we could end up with a mystery. I’m not talking about the screen going black, leaving us cut off like in  The Sopranos, nor one that tells us exactly what happens to everyone over the next fifty years (like the ending of Six Feet Under), or one that brings us to some confusing spiritual epiphany (like Lost),  but rather one that allows us to imagine what comes next, one that gives us the freedom Don is seeking.

This isn’t so much a prediction as a wish. Previously on Mad Men, Don Draper left the building. If the show isn’t moving toward the man once known as Don Draper deciding or having already decided to shed the Draper identity, then it’s given us enough red herrings to cater a Scandinavian wedding. The question is how exactly will all this come about. Will he return to being Dick Whitman, or become someone else? And do we need to know the details?

I say we don’t. The problem with Don becoming Dick (again) is that too may be a trap, and not just in a literal sense with Dick’s desertion and fraud hanging over his head. A name comes with a past, and Don is leaving his behind.  Is it important what he calls himself? Bert Cooper (who made a recent cameo from the great beyond and previously told Don that the best things in life are free) didn’t think so.

We’ve been given hints — enough to speculate about what’s to come. Is it a coincidence that the hitchhiker Don picked up could have been his younger, bushy-haired doppelgänger?

What if there were another accident and the passenger got killed and burned beyond recognition in the fire? Once again, miraculously, Don/Dick walks away – but not before planting his wallet on the corpse, ensuring no one will look for him, and the kids can inherit. Too neat by half. Contrived, and a cheat. The resemblance between Llewellyn Davis and Don was like Megan’s wardrobe and reading choices, intentional and meant to throw us off.  They won’t go there.

A slow realization that Don is gone would be the classier route. Meredith might reach out to Betty who reluctantly calls Megan or asks Sally to do it – just to check if she’s heard from him. Maybe that’s why Betty seems so preoccupied in the preview, and Don is not present (unless that’s a tease to foster just this kind of speculation). They could move on to tie up the fates of other characters, OR maybe, and this would absolutely be my dream-ending – Don’s ill-fated Hawaii commercial will come true. Don’s car will be found at the edge of a cliff overlooking the Pacific, and there on the driver’s side his suit would be laid out, hat and tie included. Remember that night when he put on his suit before Diana came over? She thought it was odd and asked him about it. He told her it was his “vanity.” He needs to shed it to move on.  Bert Cooper would have admired the zen of the thing. Like his family and colleagues, we’ll never know for sure if he jumped into the ocean or walked away to another life.

Then again, the title of the upcoming episode is The Milk and Honey Route. Google it, and you’ll get “a handbook for hobos” published in 1931. We heard about hobos back in episode 8 of season one. A hobo did some chores for the Whitmans. Don’s stepmother allowed him to sleep in the barn. Young Dick brought him blankets and they spoke. The hobo had once had a more “normal” life. Freedom was a choice. In another bit of self-reference, that episode also featured a couple (Don and Midge) planning an impromptu trip to Paris that never happens. The penultimate’s title, along with the season one Hobo Code episode, leaves the impression we might actually see Don/Dick beginning his new itinerant life, but maybe that’s just the writers misleading us again, or merely hinting at one possible fate. Perhaps the hitchhiker was reading the book, and left it in the car for Don, who carelessly or purposely left it on the passenger seat — maybe as a clue to Sally that she didn’t need to mourn him. Or maybe he just wanted her to think that.

Dead or alive? Ultimately, we’ll all be dead soon enough, so what’s the difference?

(If you found any of this intriguing, or just thought “good try” then please take a look at my oeuvre over here. And remember, I don’t get any money unless you pay me.)