Given what we saw in the sixth season of Mad Men — Don Draper repeating many of the same mistakes he made with Betty before finally hitting rock bottom — the redemption arc we saw for Don Draper in the first half of season seven was unexpected in what looked increasingly like the story of a tragic (anti-) hero. Nevertheless, the mid-season finale in my opinion ended on an optimistic note: The astronauts landed on the moon, Bert Cooper got the perfect send-off, Roger Sterling wrestled SC&P away from Cutler and saved Don’s job, and Don and Peggy reunited as creative equals and close friends. Even Don’s break-up with Megan felt right.
The question for the final seven episodes, however, is whether Don and the rest of Mad Men’s core cast will continue their ascent, or if the deal with McCann Erickson will prove to be disastrous. In my opinion, I think both: The McCann deal will be bad for SC&P but ultimately good for its employees, who — like Bert sang in the mid-season finale — continue to find that the best things in life are free. I like to think that the mid-season finale was not a peak for the characters, but the mid-point on their way to their respective happy(ish) endings.
To that end, I’d like to see happy endings for all the characters. I’m not saying that it’s they’re going to get them. This is not a prediction. Or a theory. This is just what I’d personally find to be satisfying endings for the various characters, and they make some sense in the context of the series.
Megan Draper — Megan and Don do not get back together, but they do remain friends. In fact, Don makes good on his promise to take care of Megan by doing for her what he couldn’t do for Betty: He puts her in an a national advertising campaign and she becomes something of a minor celebrity (I’m thinking Joan’s Avon account). During one of the ad shoots, her and the man who has been most obsessed with her all along, Stan Rizzo, end up hitting it off and are an item when the series ends on New Year’s Day 1970.
Betty Francis — Betty, I think, will finally divorce Henry, who has turned out to be a sexist pig all along. I’m not entirely sure what her perfect ending will be, but it would probably involve moving back to the city, engaging in low-level Republican politics, and hopefully ceding custody of her children to Don. Or anyone else, really. Betty’s not dumb (she speaks Italian!), but she is a terrible mother. (The zany fun ending would have her actually teaching Italian).
Pete Campbell — It’s perhaps not what he deserves, but what Pete wants is to reunite with Trudy, and I think ultimately it’s what he gets. He’ll have to eat a lot of crow, and not only agree to move back to the suburbs, but he’ll have to quit SC&P and take an accounts job at his late father-in-law’s old company, Vicks Chemical, where he’ll run their in-house marketing department. He’ll be miserable, but he’ll be miserable in the way that Pete wants to be miserable: Tied down by an chatty wife and a child that strips him from his freedom (his hairline will also spoil some of his opportunities to sleep around). He’ll bitch and complain and insist he was manipulated back into his marriage because Trudy just couldn’t run the household without him, but secretly, it’s Pete who will come back on his hands and knees begging for forgiveness.
Roger Sterling — Ultimately, I don’t think that the merger with McCann will work out. The Chevy deal will fall apart and McCann — with 51 percent of SC&P — will dissolve the company (though, they will have to pay out the five year contracts and agree to give the SC&P partners their millions) and Roger will be forced into retirement, which he ultimately embraces. He fully reconnects with his ex-wife, Mona, and not only helps her to raise Margaret’s child, but he ends up playing an important role in the life of his and Joan’s son, as well. He becomes the father and grandfather that he never was, and discovers that it’s where his true happiness lies.
Joan Holloway — Joan wants two things: She wants to find true love, and she wants to earn her success, and I believe she gets both. Looking around the entire Mad Men, I’m not sure who could possibly be a potential suitor, but I kind of like the idea that she ends up falling in love with Alan Silver, the professor who gave her a crash course in marketing in the season premiere. They had some interesting friction.
When SC&P is dissolved, only Joan (and Harry) end up being absorbed into McCann. Joan, in fact, has enough of her own clients to eventually become a named partner in McCann Erickson. (McCann will keep Harry because he’s the only one who knows what to do with the goddamn computer).
Ken Cosgrove — With his severance, Ken Cosgrove takes some time off to return to his first passion: Sci-fi novels. He never goes back to advertising.
Ted Chaough — The deal with Chevy ultimately falls apart because of Ted, who really didn’t want to get back into advertising. The falling man in the Mad Men title sequence? That’s Ted. I mean, SOMEBODY has to be the falling man, right? And if it’s anyone within the existing universe, my money is on Ted. His death results in the dissolution of SC&P.
Lou Avery — Don kicks him to the curb in the 2015 premiere, but what do you know? His comic strip ends up becoming a syndicated hit in a handful of newspapers, mostly in the midwest.
Sally Draper — Who the f*ck knows? One thing is for certain, though: Sally is going to be just fine.
Don Draper and Peggy Olson — Don Draper is partially based on an ad exec Draper Daniels. This is how Draper Daniels met his wife, as told by his wife Myra Janco Daniels, the executive vice president of Leo Burnett — the first woman to hold that position — with whom Daniels’ had a “collegial” relationship, and with whom Daniels had worked on many creative campaigns.
From Chicago Magazine:
I asked, “Are you going to sell me with the next merger?”
“Not exactly,” he said.
He showed me the card. On one side, he had written out his own best character traits. Then he turned it over. On the other side he had written out mine. Mine were better than his, so I knew he wanted something. I thought, What in the world has got into him?
“I’ve been thinking about this for nine months, Myra,” he said, “and I think we would make a great team.”
I said, “I think we are a great team. Think of what we’ve accomplished so far this year.”
He said, “I’m talking about a different sort of merger.”
“Yes, I’ve decided I’d like to marry you.”
I lost my voice for a moment, because I had never thought of the man that way before-and had no idea he had thought of me that way. Dan was twelve and a half years older than I and had been married before. I was against divorce in those days. But more importantly, I was happy with my life. I told him that.
“All right,” he said. “Let’s talk about it again tomorrow.” And then he walked out whistling-which, to me, was one of the most maddening things anyone can do, particularly under the circumstances.
Daniels talked Myra, who was engaged at the time, into waiting a year to get married, but during those intervening months, he tricked her into getting a blood test. Then:
The next day, he picked me up to go to an Edna Arnow pottery show. On the way, he asked if he could stop for a minute at the courthouse. I told him okay; I would wait in the car while he went inside and conducted his business. He said, “No, I can’t leave you alone in the car in this neighborhood. Won’t you just come along?” So I did, and we got off on a floor with a sign that read “Marriage Licenses.” I had assumed for some reason that he was at the courthouse for a fishing license.
“Myra,” he said, “I’m not getting any younger and I think we should get a license.”
“But we have a year.”
He just looked at me. I went up to the clerk at the counter and said, “We’re not getting married. We have a year to wait. If we got a license, this wouldn’t be published, would it?” The clerk said, “If you request that it not be published, no, it won’t.” So that’s what we did. But it didn’t matter: There was a large room across the hall where marriages were performed and Dan said to me, “Myra, let’s go ahead and do it.” I couldn’t speak. But the next thing I knew, we had done it. We were married. And I started to cry.
But the thing is, those two close friends who had worked on several campaigns together and were never thought of as a romantic couple ended up very happily married. Despite the weird circumstances, Myra never ended up regretting their marriage. They remained married until Dan died of cancer.
Do I think that Don and Peggy will end up getting married under weird circumstances like Draper Daniels and his wife, Myra? Not really. I think it’s just too weird. But could there be some ambiguous overtures toward that? Maybe. Either way, these two end up together in some capacity. Perhaps they move to Pennsylvania with Draper’s millions and they open up Olson and Whitman, a small boutique ad firm.