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.