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In last season's Mad Men finale, "Close the Door, Have a Seat," Roger Sterling confided in Don how he's never had to actually build something. He inherited his wealth, his position, his relationship with Lucky Strike that has made him so essential to Draper and co. In setting out and starting up Sterling, Cooper, Draper, Pryce, he was giving himself, and those who came along, the first chance to create something new. To earn everything they have.
Some, like Pete Campbell, have embraced the opportunity. Pete, like Roger, comes from inherited wealth. But he has used this opportunity to cultivate his relationship with new clients and make a name for himself. And he has, to the extent that he's being strongly pursued by other agencies. Rival creative director and Don-wannabe Teddy Chaugh goes so far as to show up at the hospital where Pete's wife is giving birth to offer him a spot at his agency, complete with his name in the company title.
Roger, on the other hand, could not be more helpless. Last week he found out that Lucky Strike would be leaving and he begged Lee Garner Jr. to give him a month in which to work it out. And what has he done in that time? Absolutely nothing. He hasn't even told his partners at SCDP about the event. It's unclear exactly what he was waiting to occur (he admits to Joan that he didn't know what he thought would happen), but he expected something to fall out of the sky and save his ass. Somehow, that master plan managed to fail.
Word gets out early about Lucky Strike's impending departure when a former colleague runs into Ken Cosgrove at a dinner with his fiance and in-laws (Random Side Note #1: Ken's father in-law is played by Ray Wise of the classic Twin Peaks-fame, and his fiance is played by Larisa Oleynik of the not-as-classic The Secret World of Alex Mac). This sends a wave of panic through the offices of SCDP, and sends everyone scrambling to pick up new clients, pausing their personal lives. For Pete that means missing the birth of his daughter so he can go to a funeral of a colleague in an attempt to gain new clients. For Peggy, that means holding off on a new relationship, although she ends up merging the two. Using the feelings brought about by this boyfriend in her successful pitch to Playtex.
Roger, alternately, uses it as a pathetic attempt to get Joan to sleep with him again, which she refuses, much to his dismay (Random Side Note #2: This episode had multiple uncomfortable instances of men not taking no for an answer. First Roger doesn't believe Joan, bringing back memories of her husband raping her a few seasons back. And second, Stan doesn't accept Peggy's rejection of him when he mistakes her tryst with her boyfriend for an open invitation for all men in the area. All in all, I felt very awkward while watching a lot of this episode). Eventually he gets the message, leading him to sadly putting on his hat as he observes that he wishes he had known their time in the alleyway was going to be their last time.
Bert Cooper (who, for all his dottiness, has shown himself to be a very sharp observer of those around him) sums up Roger perfectly when he observes "Lee Garner Jr. never took you seriously because you never took yourself seriously." He has never had to work for anything, skating by on his considerable charm and humor, and now that he has to do more, finds himself completely unable to do so. As the season winds down, and the plot kicks into high gear (especially after how light on plot most of the season has been up to this point), it remains to be seen if this will actually sink SCDP, or if they will find a miracle cure at the last moment. I, for one, have a hard time imagining that they'll have the company go down and have next season be the second season in a row dealing with Don at a new agency. But either way, Roger's image, both in his own eyes and the eyes of others, has been irreparably damaged. It's hard to feel too much sympathy for a man who at the end of the episode is sitting in his beautiful home with his lovely, young wife. But, as he looks at the vanity printing of his (very slim) memoirs with a woman whom he has nothing in common with, it's impossible to to feel anything for a man realizing just how insignificant his accomplishments have been.