Don and Connie: As he has been all season, Hilton is a stand in for Don's father, who also got some face time this episode. We learn from Hilton that Sterling Cooper has been sold to a larger agency, one that Don—or anyone else for that matter—doesn't want to work for. Because of that, Hilton drops Don, which leaves him in the lurch because he had to sign a three-year contract to secure the Hilton deal in the first place.

But what he's really upset about is that he doesn't have his independence. He is energized by Connie's final question: is he going to be a whiner or is he going to be a winner? And with the promise that they'll do business again in the future, Connie gives Don the final push to try to take his future into his own hands.

This leads to the flashbacks concerning Don's father, who we learn wasn't happy with the price his crops were going to get in a cooperative, so he struck out on his own to do what was right for him. Instead of selling for cheap, Whitman Sr decides to hold onto his crop and sell it in the winter when it will fetch more money. Though Don tried to shed his past like a snake wriggling out of a dirty skin that was far too tight, he is still his father's son. When things aren't working out for him, he decided that he would rather do the right thing on his own and possibly fail, than succeed as an automaton for The Man.

This is later reinforced when we learn that Don's father was literally killed by caving in. When there isn't much money left, Don's stepmother convinces her very drunk husband that he has to sell his crop. He says he'll go immediately, and Don goes with him to make sure he doesn't literally fall off the wagon. But he doesn't even get on the road, when a spooked horse kicks him in the face and kills him. If he had stood by his principal and held onto his crop, he never would have been out there to be kicked in the first place, and might still be alive—or at least lived a bit longer.

While Don might be the indepence-at-all-costs, up-by-the-bootstraps, fuck-them-all-I-know-what's-right product of his father, he is determined not to be him. He is not bending over to get kicked in the face while McCann fucks him for the rest of his life.