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I recently finished Mad Men and I wanted to know if Bert actually knew about Don's past because he has always been extra affectionate towards him, something he even rarely shows to Roger during the series and even when Peter reveals Don's identity as Dick he simply says, "Who cares?"

So, does Bert know about Don's past or at least more than most of the characters on the show?

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    No, of course not, how could he? Nobody cares about Don's past, they only care about the money he generates. WRT: "he has always been extra affectionate towards him": no idea where you'd get that impression. – BCdotWEB Oct 15 '15 at 15:48
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Roger knows that Don is a go-getter and doesn't necessarily come from as glamorous a background as most people think, but not necessarily much (if anything) more than that. Remember that Roger is the one who ended up helping Don get into the advertising industry after Don - then a lowly fur coat shop salesman - made a couple of rather ballsy moves that wasn't exactly considered to be polite. As Roger Sterling's page on the Mad Men wiki site puts it:

Some time in the 1950s, Roger enters Heller's, a specialty shop dealing in fur coats to buy Joan a fur coat, where Don Draper is employed as a salesman. Roger comments on an advertisement for Heller's and Don states that it is one of his own. Roger hands Don a card showing that Roger works for an advertising firm. When Roger opens the box for Joan in a hotel room, he realizes that Don has included a portfolio; he considers Don to be "out of line" for including it.

A few days later Don runs into Roger in the lobby of Sterling Cooper, and tries to explain it away as coincidence. He asks Roger if he saw his work; Roger tells him that it was thrown away with the box. Don offers Roger a drink, and though it is 10am, Roger accepts. Over drinks, Don tries to sell Roger on the idea of hiring him. A few days later, Roger sees Don in the lobby again, waiting for the elevator. Roger is beside himself, angry that Don could not take a hint that he was not interested. Don stops Roger; while they board the elevator, he reminds Roger that he had hired Don the previous day. Don smiles as Roger appears confused about his lapse in memory. ("Waldorf Stories")

That may be part of the reason that Roger vocally states that Don's secret past doesn't matter. Not only are the two close (which is another important factor), but Roger knows from personal experience that Don's usefulness is in his talent, creativity, and gumption - and very much not in his history or family name. But there really isn't much (if any) indication that Roger already knew anything about the secret parts of Don's past.

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