The situation of Jonas Stern, too, relates strongly to the generational and gender interrogations going on in the universe of the show. A mentor to Diane and Will, we never really see him at his best. First he leaves, weirdly, and then he comes back to steal clients, and the next time we see him he's breaking down into dementia that only Alicia's allowed to know about. If Diane and Will are the "parents" of Lockhart, Gardner, Stern is an obsolete grandfather, still holding on stubbornly like something out of Steinbeck. (And let's not even start with his trio of even older Silent Partners, who come off like patriarchal mythological creatures, barely incarnate and useless as hell.)
As a map of our culture, you couldn't get a more poignant portrait of the way Boomers relate to their parents, and to each other, than the constant transitions and financial machinations in which Lockhart, Gardner constantly finds itself. Diane (and Will, for that matter) love Stern but want him gone, are beyond irritated whenever he manages to screw them without even trying, sit shiva when he leaves, and seem almost envious of Alicia's conflicted relationship with him.
In fact, it's such a universal viewpoint -- call it the Big Chill take -- that it might be worth thinking about just how different the world looks to somebody not immediately in the classic CBS demographic. As a huge fan, there's been something satisfying, not to say subversive, about watching my fellow youngsters come out of the closet about their love of the show. Watching Alicia learn what Google is, or Peter marvel over Zach's computer and surveillance skills, is something wonderful -- and again, you've got Eli Gold and his constant child problems to make even the occasional (often funny, never silly) intergenerational conflict something to enjoy.
There is a real concern, in the world of TGW, about the idea of legacy. Diane's legacy will be a generation of hardworking young women who never even had to have their hearts broken by the facts. Alicia's legacy was to raise two children with such strong convictions that they're now going rogue on her. Jackie's legacy, Peter, is so important to her that she regularly blinds herself to basic right-and-wrong. And Stern's legacy is the conflicted brilliance of his two stars, Lockhart and Gardner. Always in transition, always in flux, and yet somehow always following the chain through all three or four generations, the show's focus is timely and timeless at the same time.