He’s part gifted con man, part devilishly handsome ladies’ man and 100 percent damaged goods. He’s been an enigma to us throughout the entire seven-season run of Mad Men?, and his colossal dysfunction ever so slowly opened the door to our fascination with him.
But that’s the thing: It took a long time for us to realize just how deeply his wounds run. At first glance, he was the golden boy in the golden era of advertising going after the plum account — Lucky Strike cigarettes. Did his conscience squirm over cancer warnings of nicotine use? Nope. He flippantly proclaimed, “We can say anything we want.” Which, looking back, said a lot.
Through the years, we’ve seen Don effectively say that he was the marrying kind, that he liked living in the ‘burbs, that he could function perfectly well while swilling bourbon 24/7 and, most telling — that he has mastered the art of reinvention. Dapper pitch man or wounded warrior of life? By now we realize that he’s both; the question is, which guy will we be left with when the series ends?
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Matthew Weiner, the show’s creator, has left us almost too many breadcrumbs to follow. When SC&P was swallowed up by McCann Erickson and Don moved into the flagship skyscraper, he ever so subtly stared out of the window and then gave the window a little push with his hands. Does the show’s “Falling Man” opening sequence foreshadowing the finale? Last season, when Anna Draper’s niece, Stephanie, showed up on Megan’s California doorstep pregnant, Megan (and Don) took care of her. Will his meandering road trip through Middle America lead him back to follow up on her and her baby and start a new life of deception? There have been mentions of Charles Manson somehow factoring in and plenty of talk about a plane crash. I think the ending will be much more nebulous than that. Betty’s going to die, but I doubt the other characters’ lives wrap up as neatly. However it shakes out, I think we are meant to keep pondering about what Peggy is up to and how Roger is faring as the HIV crisis starts to unfold in the years to come. The only thing I’m sure of at this point is this: just as Weiner uses minutia and symbolism to steer us, he uses it to misdirect as well.
I’ll bite, however, at the catnip woven into the final episode before the finale, “The Milk and Honey Route.” There was something hauntingly open about Don’s demeanor once he settled in with the crowd at the VFW hall. Before we knew it, tight-lipped Don Draper unleashed one of Dick Whitman’s biggest secrets. And, was it my imagination, or did he take that phone book face-bashing like he had it coming? Weiner certainly could have been messing with our heads by having Don give his Cadillac to young con man Andy. But it was the advice he doled out that got my attention. “Don’t start your life by doing things you’ll have to run away from.”
Which brings me to my prediction. You know that smile we saw on Don’s face at the bus stop? I think at the very moment that he had no direction in the world, Don finally figured out where he was headed. He decided that not only did Don Draper die in Korea 20 years ago, it was time for his shiny portrayal of him to die too. We already know what became of Don Draper; it’s Dick Whitman that we’ll be left thinking about.
It’s clear that he’s doing his best to stay connected with Sally. When he spoke with her on the phone, he was pretty chatty about his plan to have no plan, and then warned her that money could be tight before he promised to call next week. By my calculations, several days have passed, and he’s about to get the news that his children are losing their mother. Details like how he makes a living and whether he can ever sustain a marriage will be left for us to sort through on our own.
Dick Whitman is going home.