Unless that flashback wasn't accurate for some reason, the family (to me) looked rather well off and not the kind of childhood I'd be ashamed of. Except for the hair cut.

Maybe his mother worked for the family? I definitely get the impression that Don grew up working class.

I saw the flashback as Don being introduced to his new half brother. How old is Don? When do we think he was born?

There was a fairly high mortality rate at the time (if I remember correctly) it wouldn't have been uncommon for a mother and child to die in childbirth, or his mother could have died from some illness. It's not a far stretch from that for Don's father to favor his new wife and son over Don. Especially if he considered Don to be a "difficult" child after his mother's death and thus be distant to him.

Or Don could have been sent to live with relatives until his father remarried and had made a "suitable" home for him. It wasn't uncommon for children to be sent to live with relatives. Both my parents had cousins live with them for various reasons.

I definitely get the impression that Don grew up working class.

Yes. The fact that Adam is a janitor points to this as well.

Ahh, thanks. So the two are partners, not Boss & Underling.

I'm now 3 episodes behind, but I think it's Boss and Former Boss/Partner's Son. In the second or third episode when Don and Roger get called in to Big Boss's office, they reference a picture where it seems that Roger is a little kid on someone's lap so I took it to be that Roger's father founded firm with Big Boss.

Also, I'm loving their attention to detail. Peter's "old money" family vacationing on Fishers Island is spot on in and of itself, but the fact that that's where the the Bethelem Steel heir's mansion actually was (way back when) is just perfect.

Ah, megan, that would work for the dynamic we see.

I think it's Boss and Former Boss/Partner's Son

Thanks, Megan. Makes sense.

Yeah, that's got to be it -- Roger is definitely the junior partner, so that explains "his" name coming first.

I knew something was up when they gave us the shot of Don's hands and the money as the elevator doors closed,

I totally missed that! Possibly because I was getting dip in the kitchen.

This is taking place in 1960, right? Too bad it would have to go four seasons before The Feminine Mystique comes out in 1963.

Did you have a Chip-N-Dip?

Sadly, I did not. But just imagine what those guys will think of Gladware!

Oh, and I definitely thought they were setting Don up to be Jewish, until they showed his family.

his mother may have been jewish.