Meanwhile, the firm has descended into chaos, mirroring the chaos in Chicago. Michael Ginsberg and Jim Cutler fall into a semi-hysterical shouting match, with Bob Benson improbably getting in the middle, thanks to having listened to a motivational album beforehand. Ginsberg’s meltdown starts to seem less political than emotional-health-related (“I can’t turn off the transmissions to do harm,” he tells Bob later), and Jim’s asking Bob to step up proves to be more political than genuine, since Jim can see that Bob’s empty ambition might be easy to manipulate. By the time Ted and Jim yield the name of the firm to the other team, it’s clear they’re up to something, and Don and Roger (and Bert Cooper) look poised to lose control of the whole firm. (For all of his flaws, whenever Pete is yelling that trouble is afoot, you know he’s on to something.)

The episode’s most satisfying moments, though, are served up by Joan and Peggy, who somehow manage to 1) snag a new client, 2) air all of their long-buried resentments toward each other, 3) screw up the whole power play but good and then 4) save themselves with a brilliant Hail Mary pass by Peggy. Seeing Joan unintentionally land a spot as an account executive might just qualify as one of the best moments of the season so far. Joan is a great character not only because, unlike many of those around her, she’s at once competent and ethical, but also because Matthew Weiner has found ways to make us care about her. When she’s jilted, marries the wrong guy, or is shamed by others at the office, we always feel her pain.

In contrast, though, seeing Roger and Don soaking wet and stunned by the side of the pool didn’t have the emotional weight that it should’ve had, and it really drove home just what we’ve had to endure this season: the inversion of some of “Mad Men’s” greatest charms. The whole season has played out like the end of the second act of a movie, when the protagonist hits rock bottom. The big difference is, Don’s rock bottom will last 13 hours – or even longer. After watching this guy slip out of countless tight spots with his pride intact, his money untouched and a bevy of lady admirers always waiting in the wings, we now have to see him shatter into a million pieces in slow motion. That might be fine if it happened all at once, but having his damnation play out over the course of a full season turns out to be pretty anticlimactic. We can see that Don’s going to flail and grow increasingly confused and never learn a thing about what he’s done wrong, possibly even after he’s lost everything. In fact, as unlikely as the Sharon Tate predictions might seem (Megan was wearing a Vietnamese red star T-shirt like Tate once did, and will therefore end up murdered), it is tough to imagine the season wrapping without Megan dying or Don almost dying or both.

In fact, every time those two say goodbye to each other, it feels like it might be the last time they speak. Particularly now that Don’s at least trying to pretend to be a good husband, Megan looks truly doomed. For all of her flaws, she seems to represent a youthful mind-set, a political conscience, and an earnest drive to pursue an artistic career (even if her actual work on the soap opera is somewhat meaningless). If any one act could signal a terrible end to a terrible year that looked to some like the death of idealism and hope, it would be Megan’s senseless death, probably as a result of selfishness and ignorance on Don’s part.

What’s made this season intermittently disappointing is the fact that we’re seeing our favorite cipher fall apart, but we’re not given much of a way to care about him as it’s happening. Even a thug like Tony Soprano elicited our sympathies when his life grew darker and darker, thanks to David Chase’s exceptional knack for putting Tony’s soft underbelly on display. Whether it was Tony’s affection for leftover pasta, washed-up race horses, or doomed women, we always cared about that guy no matter how twisted or pathetic he got. Chase would have Tony slumped by his pool in his bathrobe, waiting for the ducks to return, or he’d haunt us with a little kid singing “Four little ducks went out one day, over the hill and far away,” and we would feel the full brunt of Tony’s longing. Chase played our heartstrings like a virtuoso, and as a result, a sad, fumbling little boy always showed through in James Gandolfini’s eyes.

At its core, “The Sopranos” may have been a simpler show, a rich character study rather than a layered study of an entire era of American history. But sometimes it seems like Weiner overthinks his stories instead of feeling his way through them. Keeping “Mad Men” as entertaining as it was for five seasons is no small challenge. Still, in pursuit of so many big historical events and grand themes, Weiner has allowed us to stop connecting with Don as a human being. When he cringes, or looks disgusted, or becomes confused, or almost dies, we really aren’t all that moved. Chase made us worry all the time that Tony would drop dead of a heart attack. And watching him almost get killed sometimes felt like seeing someone point a gun at your favorite uncle. Hell, on “The Wire,” David Simon made us care deeply about a drug dealer (Stringer Bell), an assassin (Omar) – the list goes on. We should care more about Don Draper. He’s threatening to become less a great character, and more a great icon or symbol. He is the antihero of this late capitalist fable, but as his symbolic weight grows, his emotional impact shrinks.

If that seems inevitable, think of Jay Gatsby. Even though his vanity and grandiosity know no bounds, even though his aims are skin-deep, his idealism and longing remain relatable. Despite all of his power and his money, he is a vulnerable figure whom the reader (and the narrator) naturally wants to protect against Daisy’s indifference. If we’re going to care about Don Draper again, we’re going to need to see him suffering in a way that makes us feel for him.

Like Tony before him, Don can be a symbol of American greed and ignorance gone wrong, and still be a heartbreaking tragic figure whom the audience secretly (or not so secretly) roots for. But we need to understand and relate to his pain a little bit more. We need to see him want something dearly, and fail to get it. We need to see him stumble and fall into the pool, rather than having an out-of-body experience. We need to see Roger leap in clumsily to save him. We want to see something pass between them, which might make them each appear less like archetypes of a bygone era, and more like fallible, shaken men facing down their own apocalypse. The big, important themes and layers of meaning woven into the fabric of this show are all well and good, but without three-dimensional characters with emotional stakes to flesh them out, they feel more academic than soul-shaking.

At this point, Don is not only a downer to hang out with, but he’s slipped past our reach entirely. After all, he’s lost all touch with his own humanity. Even the threat of death can’t save him. “Dying doesn’t make you whole,” the (hallucinated) soldier tells him at the party, right before his near-death experience. Without any salvation or promise of redemption ahead for Don, all we can look forward to is more denial and more alienation. Or as Roger puts it, “He’s fine. Everybody back away.”