Is Don Draper a good guy? Is he capable of being one? Do, at the end of the day, the better angels of his nature outweigh his cruel-streak and sometimes blinding self-centeredness? Certainly, he's no Luke Danes or Eric Taylor--perhaps the only unambiguously good guys among prominent male characters in American television's twenty-first century renaissance. It's worth observing, though, that even Coach Taylor must overcome his own bout of selfish inflexibility in Friday Nights Lights' swansong season. Still, the ultimate decentness of these characters is never really in question. Over five seasons, Don Draper has perhaps grown more familiar and hence less enigmatic, as viewers have not only come to know some of the details of his shadowy past but also closely observed his behavior in various situations so that, when his actions sometimes appear inexplicable to other characters on the show, they make a certain sense to us. Don's moral make-up, however, remains for us as elusive as it does for his family, co-workers, and indeed for Don himself. What we think we know about our protagonist's moral compass is constantly in flux, with our assumptions and expectations confounded from week to week--something that's never been clearer (or rather, hazier) than in the show's marvelous fifth season.
To be sure, Don is a moral step up from the recent TV anti-heroes he's too often grouped with: Tony Soprano, Vic Mackey, Walter White. There's rarely any doubt on The Sopranos or The Shield that their protagonists are, morally speaking, shitbags--fascinating, charismatic, psychologically complex shitbags, yes, but almost certainly beyond redemption. Ditto Walt, who may have initially broken bad for the "right reasons," but the original premise of the series and of Walt's descent into crime are long since out the window; the chilling final shot of Breaking Bad's fourth season shows just how far we've moved beyond the moral defensibility of season-one Walt. In the grand tradition of Welles' Charles Foster Kane and John Wayne's Ethan Edwards in The Searchers, these men are not merely flawed, but doomed by the weight of their moral compromises. If anyone presents a good comparison to Don in this sense it might rather be someone like The Wire's Jimmy McNulty.
Don might perhaps remain in better shape in this regard than did McNulty after the fifth (and final) season of The Wire, considering the deeply dubious serial-killer plot that McNulty masterminds. Don's role, or maybe non-role, in the Joan-Jaguar situation does speak to a level of decency that elevates Don above the ranks of Pete Campbell(who Lane quite rightly calls "a grimy little pimp" during their fight scene) and the blissfully amoral Roger Sterling. This is not exactly rarefied moral air, granted, but when Joan says that Don is "one of the good ones," we're tempted to agree. But it's never that simple, is it? Certainly not on a show with this many moral shades of grey.
The tragic case of Lane's downward spiral this season, and Don's reactions to it, are illustrative of such fine nuances. When Don forces Lane out after finding out about his desperate financial manoeuvrings, it seems like the fairest, if not the most sympathetic or kind, course of action. Though we in the audience can clearly see the sad, awful road ahead for Lane, I really don't think the thought of suicide ever crossed Don's mind as he tried to comfort Lane by telling him that things can only get better from the rock-bottom of being fired. This is partly because Don seems largely incapable of generating anything like empathy; he is intimately familiar with starting over and reinventing himself and can't understand why this should be any less feasible a process for Lane. But Don also doesn't know what we do, in terms of the overwhelming strain that has been mounting on poor Lane all season.
The most morally murky scene, with regard to Don's handling of Lane's crisis, comes in the finale as Lane's widow tells him flat out that Lane was simply not the sort of man who could handle the kind of high-stakes ambition that energizes Don, and that the money being offered to her by the company is an insulting pittance compared to what her late husband put in, personally and pecuniarily. It's basically this season's version of the great "that's what the money's for!" exchange in last season's "The Suitcase," and Don still doesn't get it--how to say "thank you" or "I'm sorry" in a meaningful way, without having a check do the talking for him.
The finale, of course, ends on an ambiguous note, as a core aspect of Don's moral character hangs perilously in the balance. With Megan faded into the background (symbolized brilliantly within that virtuoso final sequence), after quitting advertising and proving unable to find acting work without Don's help, will Don the faithful husband lapse back into Don the compulsive philanderer? We'll have to wait until next season to find out, but my guess is that this season of increasing disagreement and disappointment between Don and Megan didn't conclude with such a scene to suggest that Don's going to respond, "Sorry, ladies, I'm taken." The acidic wisdom of Dr. Fay Miller remains on the mark: "I hope she knows," said Fay of Megan to Don, "that you only like the beginnings of things."