A Mad Men Epilogue: Choose Your "Ending"

I was thinking about the ending and reading people's comments. Here's what I came up as headcannon.

Scenario #1:

Don takes time at the retreat to reflect on his life and his traumas. He develops a close relationship with Leonard—one of the first people in Don's life that he wants to get to know and help genuinely. Don stops trying to "move forward" blindly in life and listens to Leonard's life and issues. He offers genuine encouragement to him and tells him that, in spite of Leonard's feelings of inadequacy and no self-esteem, that Leonard has accomplished more than he ever could—that Leonard has a family that Don wishes he could have again and that Don admires Leonard as a real figure of masculinity and a proper, caring father—something Don never had.

Don shares his life story with Leonard and the rest of the retreat visitors and begins coming to terms with the people he hurt and why he did it. He begins foregoing alcohol slowly and his mind becomes clearer. After spending some more time reflecting at the retreat, he decides to return to New York to begin his work making amends with everyone he mistreated. He seeks out Dr. Faye Miller and apologizes to her for the way he behaved and thanked her for helping him overcome his first major hurdle: the fear about his past. He shares his experiences at the retreat with her, though she remains icy during the encounter.

He apologizes to Peggy for not treating her like a person while at SCDP and for thinking that money was the solution to everything. He thanks her for all the work she did and shares his experiences in the retreat with her and Stan. This encounter, completely unexpected and unlike Don, amuses both Stan and Peggy and inspires them to come up with a commercial for Coke where people from all over the world are singing.

Don tracks down Rebecca Pryce in England. Don cashes out his partnership shares and sends her an extremely large portion—telling her that she was right about all the investment that Lane had made for the company. He understands if she won't forgive him, but wants to acknowledge the sacrifice that Lane made.

Don then tracks down Salvatore, who he remembered while he was at the retreat. Don finds him working in a small studio. He is now divorced and apprehensive at seeing Don, but Don apologizes privately to Salvatore for firing him at Sterling-Cooper. He offers Salvatore a job in the large art department at McCann. Salvatore is intrigued and flattered, but declines the offer. Don gives him his card, telling Salvatore to call him if he ever needs anything in the future.

Don then dedicates himself to rebuilding his family. He seeks out a therapist that he can speak with and begins the path to addressing his traumas. He purchases a small home near where Sally and Betty live and begins seeing the children deliberately as much as he can. Instead of leaving them in front of the TV, he insists on having Bobby and Gene play outside with him. Sally's relationship is more strained, but Don explains everything about his life and his childhood to her. He recounts the things he had to endure in the brothel as a kid and asks Sally to forgive him for not behaving appropriately like a father should have. He tells her that he understands if she doesn't want to be around him, but that he will always love her and be there to support her—especially in light of Betty's illness. Sally in non-committal but expresses appreciation for the effort and the door is left open for the possibility of a good reconciliation.

Scenario #2:

Don feels a false enlightenment in the retreat and doesn't address any of his past issues. While at the retreat, in his state of shallow blissfulness, he imagines a Coke commercial where people from around the world are singing. Feeling cured, he departs back for New York and asks for his position back at McCann, who are understandably suspicious about his stability. However, when he pitches the Coke ad, the creative executives are intrigued and agree to let Don back in.

The commercial is a success and is nominated for a Clio. Unfortunately, the fame and praise overcomes what little stability he had after the retreat and, like a rocket reaching its apogee, Don begins his inevitable decline. He begins drinking and philandering more. At first, he's able to maintain a façade of control at McCann, but it rapidly unravels and people at work begin to notice his distasteful behaviors. The Coke commercial becomes Don's last great work. Already on a short leash, the McCann executives see Draper as far too unmanageable an asset for such a large corporation and let him go.

For Don, with no job and no prospects, his life unravels more and more. He manages to secure a position at another large ad firm who aren't too familiar with his antics. Unfortunately, his life is now unraveling and he isn't able to produce the quality work that he used to be able to do. Moreover, age is catching up with him, and now at a firm where none of the creative know him well, they begin to snicker behind his back about the soused man, chasing girls pathetically. Slowly, the luster begins to fade from Don Draper. He clings on to his job at the ad firm through the mid-1970s, but the economic downturn is not kind to the advertising market and Don is let go.

Meanwhile, Betty has died and Don only has brief, cursory contact with his children, who are much closer to Henry and his family now. Some time in mid-to-late 1970s, Don suffers a health scare that turns up cirrhosis. He takes what jobs he can now. By this time, he is on his fourth divorce, all his exes younger than the previous, and his finances are depleted. Back to scraping by as he was in the 1950s, he enters his 50s in poor health and continues crumbling away. All his work accomplishments are now footnotes and forgotten. McCann and all the other firms had plenty of Clio nominations without him and a new cadre of young talent have taken over and eclipsed any memories of Draper than anyone might have had.

Eventually, the cirrhosis makes it impossible for Don to do any work and he is reduced to living on disability in public housing. What's left of him dies in the late 1980s. Bobby attends his funeral. Gene and Sally do not.