Mad Men Season 6: 5 Burning Questions

Ramon Ramirez is a writer for FanSided partner BroJackson.com. For more great content, head on over to Bro Jackson and check out Ramon’s work.

There are only two episodes of Mad Men’s spiraling, thick, and jarring sixth season left on the calendar. This is terrible news because for all of the volcanic change on the chessboard, this season has been more about starting fires than putting them out. All of a sudden, it’s clear that we’ll have an enormous amount of cliffhangers as we break for the show’s seventh and final season. Alliances are forming, we’re being introduced to a whole wave of new faces, and all the while Duck Phillips won’t stop popping in.

Out of the blue, useless Danny shows up to mud five minutes of valuable screen time. I’m nervous like a Tea Party rebel on election night. I hope we get answers to these five burning questions before it’s a wrap.

1. Why “Sterling Cooper & Partners?”

The delegation of old and new partners just re-named the agency at the end of Episode 10. Why go back to “Sterling Cooper?” Especially when Cutler and Chaough came up with the banner? We have never seen all out warfare between partners on the show and I think that’s where we’re headed. The notion of coming back full circle to what the agency was originally called at the onset of the decade seems too easy.

As my wife pointed out last night just before crashing, Bert Cooper let it all happen because his business savvy operates on the notion that partners would only operate with the best interest of their fellow governing partners in mind. I don’t know if it’s a malicious ploy, but Cutler has shown himself to be a ruthlessly pragmatic business man who isn’t buying into the merger like Chaough has. I think Cutler wants his name off the agency, especially in light of Chaough’s success in dealing with General Motors in Detroit, so he can have ample flexibility. He sent Bob Benson to Detroit as well, and is clearly drawing a line in the sand between his guys and SCDP’s.

The mega-agency needed to exist in order to land GM in the first place, so the guys are sort of bound together. Another split seems unlikely, yet there’s little doubt that things will only get shakier between this reluctant alliance.

2. Who stays together?

Peggy and Abe have split, which is kind of a downer. On Mad Men, characters rarely die, but when they aren’t essential to central storylines go away indefinitely. Abe had a great run as the newspaper idealist, but his arc has completed. Megan and Don have seen the love escape their marriage and it’s hard to imagine them together much longer; then again, I can just as easily see Don and Megan wanting to keep the union going for appearances.

For her sweetness and warmth with children, Megan’s true colors are that of an opportunist that wants to be famous—she has “an artist’s temperament” but isn’t an artist— when she inevitably catches Don cheating, I don’t see her as broken up about it as Betty was. Speaking of Betty, she’s at least bored sexually with Henry; her husband has been a one note saint that coaches her problems away in dark houses. I feel like the writers are kind of over it. Is Joan romantically into Bob or is he just a practical sounding board? Are Pete and Trudy finished or is he going to find a way back into his house?

3. Who is going to die already?

The message boards are so good about getting you whipped in frenzy about a character’s imminent death and then nothing happens. Megan has all of these creepy wardrobe and circumstantial parallels to Sharon Tate, and every time she is home alone we half-expect her to get stabbed to death. I’ve been waiting for Roger Sterling to drop dead since Season 1. Problem is, he’s the most entertaining character on the show and is the perpetual life of the party. But he’s almost a crutch at this point for the writers—and what demons does he have left to face?

He had that great aside with Don on the flight home from California last night where he’s talking about accepting who he is. And he’s been uncharacteristically active this season—from landing General Motors to meeting his grandchild—as if gearing up for a final hurrah. If there was any doubt as to whom Don’s closest friend and mentor is, it’s been cemented as Roger this season. From Goose to Dumbledore, drama says that the BFF needs to die so that the protagonist can complete his journey.

The creepy thing that made me shudder during this last episode was Cutler insisting on re-naming the agency, and then saying “I got an envelope addressed to Sterling, Gleason, and Pryce.” The latter two partners have already passed—no way that’s a coincidence.

4. Who leaves Sterling Cooper & Partners?

Harry Crane called this newly forged firm the “’27 Yankees” in terms of their industry appeal. Everyone at the top is comparatively stable, but middle management is growing increasingly dissatisfied. We met them as fresh faces, but Pete, Peggy, Crane, and Cosgrove are all on the cusp of their professional primes and like Draper in Season 3, everyone keeps getting more important titles above them. Pete’s already visited with a headhunter and then closed last night’s episode with a pensive toke of marijuana as Janis Joplin and the credits rolled—angry about his standing in the company.

The creative department is overrun with new wave baby boomers, there’s no way all of these faces share the same employer at the beginning of Season 7.

5. Who is Bob Benson?

Whether or not Bob Benson is a closet homosexual matters little to me. This man is here to fuck shit up and everyone knows it. Is he a spy? Is he vengeful? Is he so self-interested that he’ll spurn a beloved do-gooder? For all his kind acts, Cosgrove hates the guy and he’s always been the show’s most reliable moral compass. He tells someone his dad is dead, he tells someone his dad is alive—it’s creeping us all out.

Benson is played by James Wolk, who turned heads on the short-lived Lone Star and is a budding star that’ll be with us for the rest of the series. When we first met Benson, he pissed off Cosgrove and endeared himself to Pete, setting the table for further warfare between the rival account men. As Episode 10 closed, Benson is joining Cosgrove as a General Motors account man. The real question: Is Benson a tie-breaker or is he more ambitious?

Showdowns linger, I just hope we get answers in the next two weeks. But I think it’s going to be a Kanye West-level cruel summer.