“Two roads diverged in a yellow wood/ And sorry I could not travel both,” read the first two lines of Robert Frost’s famous poem, “The Road Not Taken”. The poem describes a man who comes to a fork in the road and struggles to decide which one to take. He looks as far as he can down each, in an attempt to determine which road is more appealing. However, as he indecisively sits and wonders of the possibilities, he realizes that the roads themselves are more or less the same. He could always pick one now, and come back to the other later, right? Well, not necessarily, sometimes the road you choose takes you too far away from your starting point. Then, all you’re left with is regret and longing for the bygone possibilities of the other road. Just as the man in the poem does, you imagine that one day you’ll come to two more diverging roads, and from your past experiences, you’ll have developed a strategy to make the right choice. You’ll just pick the one that’s “less traveled by,” you’ll think to yourself. But you’ll say it with a sigh, because deep down you know that you’re really lying to yourself.
Decisions made by strategies don’t always work out better than the ones made on impulse, because we’re all flawed, self-rationalizing beings. But it certainly feels better to have some form of roadmap to navigate through life than to just wing it all the time. In “The Strategy,” the second to last episode of the first half of Mad Men’s final season (God, that’s an obnoxious mouthful!), we find our players simultaneously stewing over the various roads not taken of their pasts, while strategizing for their own ideal endgames of their rapidly approaching – and certainly uncertain – futures.
We begin with the once sweet, but now sad Peggy Campbell. Just kidding! I wanted to see if you were paying attention. Sure, it could have been Peggy Campbell, had she taken another road, but instead, we’re left with single, childless, lonely and unfulfilled Peggy Olson. For the past two months or so, Peggy has been tirelessly working on the recently acquired Burger Chef account. Though the humbled, but still creatively potent Don Draper has been working on her team, she has managed to rein in his talents without letting him steal her spotlight. It’s hasn’t been all that glamorous, though; a lot of it has been standing in fast food parking lots, maddeningly trying to put her finger on what makes greasy burgers so appealing to families. She’s prepared what she thinks is the perfect pitch, and her superiors seem to think so, too; however, the exiled Pete Campbell is in town. Pete’s the one who brought in the account, and it’s of his opinion that Don should be the one to deliver Peggy’s pitch. It seems he has visions of Don jerking tears from Kodak executives in 1960 or, perhaps, wow-ing the American Cancer Society representatives in 1965. The timbre of his voice will lend the pitch the right amount of authority needed, the men end up deciding. But don’t worry, Peggy, you can provide the soft, emotional voice of the mother. To the men in the room, it’s a fair and logical win-win situation. To Peggy, though, it’s a cruel reminder of the very thing that she did everything in her power to prevent herself from becoming in the show’s earliest days. However, it’s also the thing that she secretly can’t push out of her mind in her present life, the role that could provide the kind of purpose and meaning that she’s been missing.
On the other end of the spectrum, we have Pete Campbell. When the show began, Pete was to be married, but he cheated on his darling fiancé, Trudy, with Peggy in the series’ very first episode. In the early seasons, we watched as their relationship surprisingly stabilized and evolved into something resembling a happy marriage, even as he grumbled about just about everything in his life. In season five (1966), Pete began aggressively pursuing extra-marital affairs. It escalated to the point that the marriage completely deteriorated in season six (1968). Since then, he’s been living a different kind of life, separated from his family by 3,000 physical and emotional miles. When he returns from California, with his plaid suit and comically receded hairline, his own daughter doesn’t even recognize him. His wife, at first, is nowhere to be seen. She’s busy, going on dates and enjoying her independence. He’s had his own kind of independence in the form of a blonde bombshell of a real estate agent named Bonnie. Up until this point, though, it’s been unclear just how serious this relationship was; however, in “The Strategy,” we learn that their needs and wants differ to a degree that it’s not going to work out. Although he’s getting a divorce, Pete is still married to Trudy. Although he resides far from the main hub of company action, Pete is still enamored with his work. All Bonnie wants is for Pete to commit to her, but once in New York, Pete makes it clear that he’s neither as over the dissolution of his family as he’d have you believe, nor is he any less addicted to his work as he was in when he lived there.
Pete could have chosen the road that led to the domestic bliss that marriage is at its best and the tumultuous terrain that it becomes at it’s worst. But he chose to veer off to another one that led to infidelity, estrangement and some level of emptiness. It sounds eerily similar to someone else we know all too well. Don Draper is another guy that seemed to have it all and flew too close to the sun. He destroyed his first marriage with a destructive pattern of bad behavior and impulsive decisions. He nearly did the same with his second one as well, but he’s aware of that now, and he’s sincerely trying to do better, regardless of the apparent disconnect between him and his lovely but self-absorbed wife, Megan. When she visits, he makes being around her a priority. For once, he doesn’t let work get in the way. When Peggy calls to gripe at him about her plight, he snaps back, but he shrugs it off and doesn’t let it spoil the mood. But try as he might, he can never quite the shake the feeling that he “never did anything,” that he “doesn’t have anyone.” There’s a certain type of despair that comes with feeling like you have neither the people nor the purpose you want in your life. Perhaps if he took another road…
“The Strategy,” in a way, is an episode of homecomings. Not only does Pete and Megan return to New York to visit their respective loved ones and the agency that which binds them all together, but so does the handsome and mysterious Bob Benson. Last season, Bob went from sycophantic bottom dweller to the de facto head account man in Detroit; the watchdog over Roger Sterling’s prized Chevy account. Bob has been somewhat conspicuously absent this season. This is probably in part due to his lack of necessity in the grand scheme of things, but also because James Wolk, the talented actor who plays him, was busy starring in a show on CBS. Be that as it may, puppet master Matthew Weiner found a way to work Bob back into the thick of things – for this week, at least. While in town for business, Bob is forced to bail one of the famously rowdy Chevy boys out of jail for “trying to fellate an undercover officer”. Bob, who was strongly, strongly suggested to be a closeted homosexual last season, is fascinated to learn that a) this man is a homosexual too and b) that his wife is completely fine with him running around with men when he’s out of town. Last season, we learned that Bob is a lot like Don Draper; he’s a chameleon, a practitioner in the art of reinvention. Just like Don, he’s always looking for either a route to a better place or a quick solution to a multifaceted problem. In “The Strategy,” Bob thinks he’s found both. First, there’s the other information he learns from the Chevy exec: Chevy is leaving SC&P, and Buick will be offering him a job. Buick is his way out, his chance to start anew, but the other revelation – the truth to the kind of life that the Chevy exec lives – kicks his brain into another gear.
Last season, as Bob faked and charmed his way up the ladder, he also developed a legitimately good relationship with Joan. He took her to the hospital once and he’s been to the beach with her son. He even carved the turkey at Thanksgiving last year! Joan couldn’t be happier to see him, that is, until he springs the ultimate surprise on her by proposing to her. You see, he’s proposing not out of love, but out of strategy. Joan can have a wealthy husband and a new life if she wants one, baby Kevin can have a real father figure, and he can be free to pursue his true sexual desires. Joan, however, knows better. Of course, she’s caught on that Bob isn’t into her; he’s into other men. (There’s always an “of course” with Joan, it seems.) She’s married for status or, at least, something other than true love before and it didn’t turn out so well. She’s not about to do it again. We know how ballsy Bob can be, but when he tells Joan that, at her age, she’s probably not going to do much better, it’s even more alarming than the proposal itself. “It’s realistic,” he pleads sadly, even after she tells him off in her ever so loving, but firm, Joan way. It’s sad, not because he sounds sad when he says it – he sounds impassioned– but because 2014 viewers watch and know that less than fifty years later his homosexuality would be exponentially more accepted. In 1969, however, being an openly gay ad man wasn’t a possible road to take.
This season, we’ve seen how the choices made and the roads taken by Don have put his and Peggy’s relationship on the rockiest terrain that it’s ever been on in the history of Mad Men. Between how Don’s treated Peggy and what he’s done to the company, Peggy literally couldn’t stand the sight of him when he returned after his leave. When he refused to cooperate with her while working under her, she grew even more indignant. Beyond all of the petty slights, though, Peggy feared that she would always be compared to him, and that she’d never get the respect that she believed she deserved. He may have once opened the door into the industry for her, but now he’s nothing but a roadblock. After she’s pressured to hand over the pitch to Don, she becomes obsessed with the idea that it’s not any good, that there’s a better idea out there somewhere. After Megan leaves, he shows up at the office to help her get to the bottom of it. She’s defensive and annoyed at first. She’s sick of him always showing up to save the day. Why can’t she figure it out herself? How does he deliver ideas as if they just came to him in the moment, anyway? She demands that he explains his creative process to her, and over time, softens considerably.
Eventually, what began as a contentious interaction evolves into one of their most touching since theirs in the seminal season four masterpiece, “The Suitcase”. Except, in this case, the roles are reversed. In “The Suitcase,” Don and Peggy bickered and battled and bonded as they hit their heads against the wall during an all-nighter, all the while trying to come up with the best pitch. Don, torn with grief over the loss of his beloved Anna Draper, disintegrates over the course of the episode until his platonically loving pupil comforts him in the end. In “The Strategy,” the two of them are once again up all night, driving themselves crazy over ads, their personal problems simmering until they reach the surface; however, Peggy has become the tortured superior, while Don is the supportive underling. The dynamics may have changed, but as they bond throughout the night, as they celebrate that they’ve found the idea that they’ve been looking for, as they slow dance to “My Way” by Frank Sinatra, it’s quite clear that they know each other better than anyone. As lonely as they think they are, they still have each other – no matter how combative that their relationship has been recently.
Speaking of combat, there was a little bit of action on the “Jim Cutler and Lou Avery trying to push Don out” front, too. Near the end of the episode, Cutler reveals the next piece of his own strategy. As a way to deflect the attention away from SC&P losing Chevy, the agency will be doubling down on its computer publicity by making the slimy and dishonest, yet loyal and forward thinking Harry Crane a partner. Don’t get it twisted, though. This is another step in the process of stripping power away from Don. Cutler’s preparing to cut loose the founder of the SC&P family, and he’s not being particularly subtle about it. (What he doesn’t know, though, is that Harry, oddly, has a reputation for being loyal to the old guard.)
Ironically, though, the last scene and the episode’s most indelible shot bring it all back to family. Don and Peggy sit side by side in a Burger Chef booth across from Pete. Peggy explains the new strategy for the pitch. It’s not about bringing take out home and the family coming together; it’s about going to Burger Chef, getting a burger, sitting down with the family and feeling at home there. Pete doesn’t quite get it, but Don backs her up, and he agrees to go along. As the camera pans out, it reveals our three season one protagonists eating together amongst organic families. Don once had the kind of picture-perfect family that you’d imagine dining together and threw it all away. Pete had a beautiful wife and daughter, to boot, and did the same. Peggy could have tried a relationship with Pete after he got her pregnant in season one or made things work with long-term boyfriend Abe, but she chose career over family. While they’re sitting there, they’re undoubtedly thinking about how the road not taken might have made them more like everyone else at the restaurant. But as they sit together, stuffing their faces with greasy food, they’re their own type of family, brought together by the roads that, for whatever reason, they actually took.
Blake Baxter is a native of Illinois and a 2013 graduate of Eureka College. He currently writes about sports and culture for Yahoo Sports and Yahoo Voices, and previously covered the Carolina Panthers for Football.com during the 2013 season, as well as college basketball for ESPN Louisville during the 2012-13 season. He has also written about sports, pop culture and politics for The College Fix, The Wine and Cheese Crowd and an assortment of newspapers. Blake works in the communication and marketing field for Technical Solutions & Services, but aspires to write full-time in the near future.