Jim Hobart pursued Don Draper for a decade without understanding him at all. He called him his “white whale,” which was an incorrect analogy. Moby-Dick was an indomitable force of nature who reaped havoc on those who hunted him. Don Draper is more of a wild stallion, which can not be possessed, because once you have stabled him, he ceases to be wild. Don can not fit into the corporate milieu; Hobart doesn’t realize this because he is use to bending people to fit his mold.
SC&P may have been representative of the sexism of the times, but it was benign compared to the blatant, abusive and predatory version at McCann. Joan is indeed lucky to have options other than submission or litigation, as either would have brought her misery.
As Bert said, Roger was not a leader; he is too naive. To be a great leader, one has to understand the nature of evil, and evil lives at McCann. So, he drinks, and plays the organ. But, he has Marie, who understands evil, and will make sure he survives intact, because he is her last shot at happiness.
As is always the case, the young will adapt to the new regime, either because they are more pliable, or because they must. Harry is happy, and Pete resigned. Peggy, of course, was magnificent, unwilling to submit until things were set straight, and then striding into the fray, looking more intimidating than intimidated, with Bert’s erotic Japanese painting, suggesting she needs more than a man to satisfy her.
And wither goes Don? He is in search of a woman to rescue, a woman to give his life meaning. But, with the exception of Anna Draper, he has disappointed every woman who has ever loved him. Can he really change, and even if so, will he get another chance?