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Top-10 Mad Men prop bets for Season 6

18 June 2012

I spent part of Sunday catching up on my Mad Men viewing (I had six episodes to watch on my DVR). It's been strange not being part of the national Mad Men conversation for the last six weeks. But watching the six episodes in a row changed the way I enjoyed Mad Men so much that I have to consider doing it again next season. (There's a gambling connection here. Really, there is. I'll get to it. Just bear with me for a couple of more paragraphs.)

Mad Men is so brilliantly written, I felt I was watching one continuous story, rather than six episodes of one show. The details and story lines meshed seamlessly. I didn't have to wait a week to find out what happened next. And seeing it all in context papers over the disappointment I might have had with individual moments or shows. If I'd watched these shows as they aired, I would have been disappointed with the anticlimactic season finale. But instead, I was able to enjoy the story much like a book or a movie, absorbing it all at once, and appreciate the fact that the finale was a nice denouement for the season.

Did I miss being part of the national discussion? Yes. Reading Slate's Mad Men TV Club discussions, Grantland's Mad Men Power Rankings and talking about Mad Men with my friends (who were great about not revealing any spoilers) created a social touch point and different sense of enjoyment that I missed -- discussing plot points, details of the era and trying to figure out where the writers and the show would go next.

So with that in mind, I take up the role of bookie this week and set 10 betting lines for next season's Mad Men. Consider this my return to the national Mad Men conversation, an attempt to predict what will happen next season and advice to Vegas odds makers looking for some fun prop bets to offer.

10. What year will it be when Mad Men returns?
Guessing what year Mad Men will be set in is the original Mad Men parlor game. The first season of Mad Men was set 1960. Season 2 skipped ahead to 1962. Season 3 skipped ahead a few months to 1963. Season 4 covered parts of 1964 and most of 1965 -- with about 10 months passing between the end of the third season and the beginning of the fourth season. The fifth and most recent season started in the spring of 1966 and ended at least a few months into 1967. So when will Season 6 begin?

It's been widely reported that show creator Matthew Weiner will pull the plug on the show at the end of Season 7, so there are only two more seasons left. But there are three really historically juicy years left in the decade. 1967 had race riots, rising opposition to Vietnam and the launch of the magazine Rolling Stone. In 1968, Martin Luther King Jr. and Robert Kennedy were assassinated. And in 1969, man first flew to the moon. So there's a lot to cover. My best guess is Mad Men returns in September of 1967, where it doesn't really have to deal with the awkwardness of its racial ambivalence, but it can still note it and the impact it had on culture and society. That's why I'm making 1967 the even money favorite.

1967: 1/1
1968: 12/1
1969: 50/1

9. Will Don land the Dow account?
A potential juicy storyline suggested to me by a coworker is Don lands Dow and the "napalm account," which becomes a significant bone of contention in his marriage as Megan becomes more involved in the anti-war movement. I like the natural progression of this storyline, so Don landing the account is a slight favorite.

Yes -110
No +110

8. Will we see the cover of the first Rolling Stone magazine?
Rolling Stone wasn't always the glossy magazine it is today. When it launched in November of 1967, it looked more like a newspaper. A picture of John Lennon appeared on the cover the first issue, and it will be interesting to see if Mad Men notes this iconic moment. This is a 50/50 proposition for me.

Yes -110
No -110

7. Will Don cheat on Megan?
Season 5 closed with Don facing another opportunity to cheat on Megan. I think the emotional growth we've seen from Don over the course of the last season is for real, so I don't think he'll cheat on her because he has his competitive advertising mojo back. I do think he could cheat on her as the next season progresses because he'll see more of "insecure" Megan and less of the hyper-competent woman he fell in love with (more on that later).

Yes 3/5
No 8/1

6. Will we see Peggy next season?
Peggy is working for a new agency now. But that doesn't mean she won't be part of the narrative of the show. Don has a lot of affection and respect for Peggy. And I suspect deep down, he'd rather see Sally grow up to be more like Peggy than Megan or Betty. So there's definitely room in the Don Draper universe for Peggy. More importantly, it's easy to keep her character going in the background with talk about her success, so when she occasionally shows up to pitch a client Don is wooing, it makes sense. But because the actress who plays Peggy, Elisabeth Moss, is working on other projects, scheduling can be an issue.

Yes -110
No +110

5. Will Pete divorce Trudy?
Pete has finally realized he hates his private life. Being a dad does nothing emotionally for him. Living with Trudy drives him nuts. And he hates living outside Manhattan. The big question here is what is Pete going to do now that he understands there's something missing from his life. My guess is the apartment in Manhattan (away from his wife) is going to keep the marriage floating for another season.

Yes 15/1
No 5/6

4. Will Roger Sterling wear bell bottoms?
Roger is enjoying LSD trips. But will he take the plunge into bell bottoms? I doubt it. While Don begrudgingly allows Megan to influence his style for casual wear, Sterling lacks a strong, youthful external force to push him down that road. He seems to have no problems attracting younger women for a roll in the hay with his power suit and well-moneyed persona. And he'll probably view bell bottoms as another sign the country is headed in the wrong direction.

Yes 30/1
No 1/5

3. Will Ginsberg quit or be fired?
Michael Ginsberg is the heir apparent to Peggy on Mad Men. But unlike Peggy, who could both worship and hate Don at the same time, Ginsberg seems only capable of disdain towards his boss, and everything he thinks his boss stands for -- laziness, shortcuts and jerks that buy Jaguars are few that come to mind.

Ginsberg's talent is undeniable. It even makes Don feel insecure and competitive at times. But Ginsberg also appears to be struggling in post-Peggy life at the firm, and his inability to see things from the client's (and women's) point of view has already rubbed one customer the wrong way.

Don respects Ginsberg, but has little patience for him. I suspect Don won't fire Ginsberg because he needs him. But that's no lock.

Quit/fired 5/1
Keeps job 4/5

2. Will there be more than one black employee?
Right now, the only black employee of note at Sterling Cooper Draper Pryce is Don's secretary, Dawn. And the firm only hired her when an attempt to make fun of/humiliate another agency backfired. But with race playing such a central role to the events of 1967, it might force Sterling Cooper Draper Pryce to appear more progressive. Of course, being more progressive for the name partners at this agency probably means more tokenism. But that seems to be the norm for ad agencies at that time.

Yes -- 5/1
No -- 5/6

1. Will Don and Megan divorce?
Don still loves Megan. That's part of why he landed her a gig in a commercial. Even though he thought it would be better for her to land the part on her own, he watched her audition reel, was reminded of why he fell in love with her and felt compelled to help her because she wanted him to. The only problem is that the audition reel isn't why Don was so infatuated with her. Don was in love with Megan's competence and confidence. He loved the fact that she so easily handled his children -- and everything that came with them -- so well. He loved the fact that she thrived in advertising with no training for it, and without his help. He loved the fact that she had great instincts when it came to dealing with Betty and his family. He loved her hyper competence.

But when it comes to acting, Megan is extremely insecure. She needed an evening quickie to work up courage for her audition. She needed Don's help to land a part in a commercial. And her mother can strangle her confidence when it comes to acting with just a word or two. That's not the Megan Don loves. But that's the Megan that's emerging and beginning to take hold. And if you combine that with arguments over Vietnam, which I suspect are just down the pike, this marriage is in for a rocky ride.

Will they get divorced? It's hard to see that happening in a year. They still have some marital bliss left in them. And Don is of the age that he doesn't want to be divorced twice. I like the no bet here. But with only two seasons left in the show, this is likely the defining year of their marriage.

Yes 10/1
No 2/5
Vin Narayanan

Vin Narayanan is the former managing editor at Casino City and has been involved in the gaming industry for over a decade Vin is currently based in Hong Kong, where he runs his own consultant group and works as head of gaming and public relations for Mega Digital
Entertainment Group.

Before joining Casino City, Vin covered (not all at the same time) sports, politics and elections, wars, technology, celebrities and the Census for, USA WEEKEND and CNN.

Vin Narayanan
Vin Narayanan is the former managing editor at Casino City and has been involved in the gaming industry for over a decade Vin is currently based in Hong Kong, where he runs his own consultant group and works as head of gaming and public relations for Mega Digital
Entertainment Group.

Before joining Casino City, Vin covered (not all at the same time) sports, politics and elections, wars, technology, celebrities and the Census for, USA WEEKEND and CNN.