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This is a "Wild Mass Guess" entry, where we pull out all the sanity stops on theorizing. The regular entry on this topic is elsewhere. Please see this programme note.
Mad Men
Pete's Gun will become a Chekhov's Gun

Harry will leave the firm.
  • Tensions between Harry and the partners are at a high point as of seaon 6, episode 4, to a point where he even threatened to leave if Joan fired one of his employees. Peggy doesn't need the extra muscle, but Harry letting go of SCDP and joining the hip young firm it would reinforce season 6's running theme of the past.

The Draper kids will experience Soap Opera Rapid Aging Syndrome if the series lasts past about 1967, possibly before.
  • At their current ages, Sally will still be too young to drive when Woodstock occurs, and Bobby will still be in High School when the Vietnam War draft ends. The series has already shown a desire to hit on every turning point of The Sixties, thus older kids are needed.
    • They don't have to be involved in those events. For example, with the Vietnam example, they could have Don Draper interacting with some of the draftees and volunteers, and him feeling the differences between Korea and Vietnam.
    • There's also the amount of turning points missed, such as the civil rights movement, the barely touched upon pop art during that era, the Beatles and Rolling Stones, the radical feminists, and that they wrote out Sal mere four years before Stonewall. From this point of view, it rather seems that they are going out of their way not to touch upon the turning points.
      • Events of the Civil Rights movement are seen on TV, and Paul Kinsey travels south with his African American girlfriend Sheila to take part in the marches. Nothing much about Pop Art, granted, but boss Bert Cooper owns a Rothko. Sally and Don go to a Beatles concert, and Don gets Sally a Beatles album for Christmas. The feminist movement came later. And, let's face it, the Big Events of the 60's have become predictable. It's refreshing when a show integrates them into the characters' lives but they aren't the main focus. The big exception was the Kennedy assassination.
      • Pretty much Jossed. They're talking Emmy nod now for Kiernan because of how much Don's home life turns on her. While the Beatles are getting touched by her and Don connecting and it's Don who gets the stones as his power walk music. Peggy is going to be the one dealing with sexuality and feminism though.
      • Also, given the amount of mischief Sally has been getting into lately, there's still some small possibility she finds herself at Woodstock even if she is a bit young.

Don really is going to write an autobiography.
  • Maybe he was kidding when he said it to Roger in Season 1 but after the events of all these seasons maybe he decides to use his flair for words to put his life into perspective.
    • Maybe he'll follow Roger
  • In one episode, Don stated that he was a "lousy student" and never wrote more than three consecutive paragraphs before in his life. On the other hand, that was when he was starting a journal, so maybe he could build from there.

Don is the guy jumping off the building in the opening credits.
  • Which could be the ultimate foreshadowing with Don at one point attempting suicide.

Sterling is the jumper in the credits.
  • After the whole losing Lucky Strike and not telling the others about it fiasco, he's looking dangerously close to losing it entirely.

The jumper in the credits is Lane.
  • As of the end of the latest season, he has lost everything. He's been fired and disgraced for forging Don's signature and embezzling money from the company, he has British loan sharks breathing down his neck, and his wife just blew what little money they had left on a brand new luxury car. The last time we see him, he's hunched over in the parking garage, literally puking with desperation and panic. If he doesn't kill himself, his father or his wife's family will.
    • Um. He hanged himself after getting fired. It was featured quite prominently at the end of the episode where he got fired. We saw the body.

Grace Holloway is the daughter of Joan Holloway
  • She's just the right age and they look a bit alike, even having similar red hair.
    • Where does Grace Holloway fit into this?
      • Maybe she's distant relative who Joan decides to name her daughter after.

Lane Pryce is related to Wesley
  • Or Mr. Hooker! They share a certain ineffectuality.

Sterling is related to Roger Sterling.

Don and Peggy will hook up
  • Don is widly believed to be based on an specific advertising great who started his own firm and married a former secretary who became a copywriter.
    • This seems really close to happening as of episode seven of season 4, but is averted for now.

Trudy Campbell will have a miscarriage
  • You know to spice things up in their relationship.
    • JOSSED. Trudy and Pete are now parents of a perfectly healthy baby girl.

The early '70s were/will be lean years for SCDP.
  • The bad days will begin when cigarettes are banned from advertising on US TV in 1970 and end when the first Honda Civic debuts into the 1974 oil crisis. Since Lucky Strike is Sterling's pet account and Honda is Campbell's, this will set up a very interesting dynamic to watch.
    • The basics of this may still happen, but as of the most recent episode Lucky Strike has dumped SCDP setting the lean years up in the mid 60's.
    • Also, the Honda Civic is precisely the car account you would want to have going into the oil crisis. SCDP's execs viewing the Civic account as a mere consolation prize is a case of It Will Never Catch On, and possibly foreshadowing if indeed the show's story takes the firm into the 70s. Between quieting tobacco ahead of the rest of the industry and landing a fuel-efficient economy car account a decade before the oil crisis, SCDP is poised for a huge comeback in the 70s.
      • But it looks like the car account they have at that time will be the Chevy Vega.

Samsonite=alcoholism for the Mad Men writers.
  • Thus far, of course, we only have the evidence of "Six Months' Leave" and "The Suitcase," but it is kind of interesting that two episodes that deal with alcoholism also involve Samsonite in some major way. "Six Months' Leave" is kicked off by Freddy Rumsen passing out and pissing himself during a pitch to Samsonite, and "The Suitcase," which showcases the beginnings of Don's inevitable alcoholism (the puking should be a clue) and the depths of Duck's (every time he shows up), as well as mentioning how Freddy is now that he's joined AA (Roger isn't pleased), gets its start with Don and Peggy working late on the Samsonite campaign.

Megan is not her real name/she is hiding something
  • "Megan" was a really rare name in North America in 1940 (when she would have been born), even less so for a French-speaking household in Quebec. Either she changed her name when she came to New York, or she's Don's counterpart in more ways in one...
    • She seems to smirk when Don's not looking implying she's been working toward her goal in being the new Mrs. Draper.
      • Word of God indicates otherwise, with Matthew Weiner and Jonathan Ingla being very clear about Megan's sincerity in the audio commentary for "Tomorrowland".

The guy falling in the opening sequence is no-one
  • It's purely symbolic of their lives falling apart, not a specific allusion to someone attempting suicide.
  • It's mentioned off-hand in one of the commentaries that one of the junior executive characters (likely Harry Crane) was going to jump off the SC building early on, but the writers decided they like the cast too much to do it, turning the credits into The Artifact.

In Season 5, the cast will go see How to Succeed in Business Without Really Trying
The movie came out in 1967; Season 4 ended in 1965, so Season 5 will start at least half a year later. There's no way they're going to miss out on a Robert Morse Casting Gag.

The company will now be Sterling Campbell Draper Pryce
With Bert gone, they don't even have to change the initials. Additionally, Ken Cosgrove and Harry Crane might be added as partners.
  • Bert seems to have changed his mind about leaving in between Seasons 4 and 5.

Pete and Trudy are Annie Edison's grandparents
Per this Jezebel comment

The silver/red interior '65 Coupe de Ville is Don's last Cadillac, for a while at least.
As he gets into his mid-40s in the late '60s he's likely to want something sportier and more youthful, and that '69 or '70 model (Mustang? Corvette? something European?) will be due for replacement right about the same time as the aforementioned 1973 oil crisis.
  • Don doesn't seem like the type to buy a pony car or a sports car, perhaps a Nova coupe. Nothing fancy, but Novas made decent muscle cars. If the Oil Crisis is a big concern, they were also available with four and six cylinder engines. And even then, he seems more likely to drive luxury cars by this point.

    If anything, he's more likely to buy an Eldorado or a Tornado when he decides to replace his De Ville (probably around 1968 based on how long he seems to own cars).
  • With a Chevy account, a Corvette maybe? Plus the Chevy Vega launch should intersect nicely with Sally's driver's license, giving them plenty of time to bond while he's giving her rides home from places the Vega he proudly presented her with took her (but failed to bring her home from).

Don Draper is no creative genius. He gets all his information through time travel.
The evidence is abundantly clear. When he still lives with Betty in their family home, when Betty goes into his office to snoop through is drawers, there's a copy of W.E.B. Griffin's book, "The Corps," which wasn't published until 1986. The only way Don could have gotten this book is if he traveled to the future and came back with it.

Ken Cosgrove is Captain Hastings' son.
He looks startlingly like Hastings, and has the same forgetable personality as Hastings, and he's of the right age for it. Perhaps Hastings had an illegitimate son somewhere in America in the mid to late '30s, and may or may not have known about him.

Don has crashed more than one car through drunk driving.
In the pilot, he drives home in a 1959 Oldsmobile Dynamic 88, and two episodes later he's driving a 1960 Buick Invicta convertible, which he drives for most of the season. Then, in season two, the Dodge Polara shows up, which he crashes halfway through, and replaces it with the Cadillac.

Betty, meanwhile, drove a 1957 Ford Country Sedan station wagon from the pilot until season three, when her father dies and leaves her his 1961 Lincoln Continental.

So, the reason those cars disappeared without explaination is Don crashed them. The Cadillac is a turning point - it's a symbol that he's 'made' it - which is why it was detailed when he buys it.
  • Betty did have a newer wagon - a 1962 Mercury Colony Park - but only briefly before inheriting the Lincoln. Not that that affects the point.

Bob Benson is a serial killer
There's nothing that supports this, but there's something creepy about him.
  • I've heard people speculating that he's going to be the one who kills Megan in the crazy "Megan is Sharon Tate" theory going around.

Megan will become pregnant, and then get murdered, by the end of Season 6
I speak of course of the Sharon Tate Conspiracy Theory, where Megan has been wearing many outfits Sharon Tate did shortly before her murder.

Bob Benson is a homunculus
That's the reason he's always got that coffee, since his ourobourous tattoo is located on his palm. Or maybe he's actually Envy in his latest disguise. He's decided to investigate SC&P because he thinks Don would make a good candidate for human sacrifice. Of course, the problem is he doesn't realize he's actually Dick Whitman, he thinks he's the real Lieutenant Don Draper who died who was secretly a powerful State Alchemist. When he finds this out he goes on a violent rampage which is how Megan gets murdered.

Bob Benson is a rare male Puella Magi
His wish was to become part of a top Madison Avenue advertising firm, which is why he just appeared out of nowhere. The real reason he's hanging around Joan so much is because Kyubey senses that Joan has magical-girl potential, and Bob is the veteran to help show her the ropes. Also the big event at the end of Season 6 is Bob turning into a witch.

Pete Campbell is going to leave SC&P at the end of Season 6
Okay, here's my actually serious theory. I think this is the most likely "bomb that will be dropped" of all the theories floating around right now. We've seen him meet with Duck to "discuss his options." He's clearly dissatisfied, about the name and about everything else, and seems to be the only person from SCDP who realizes what Cutler is trying to do in terms of slowly taking over the firm and filling it with their guys. Who knows, maybe he'll even quit advertising altogether. But he's clearly at a stand-still in his life, and he seems about to do something rash. Him smoking the joint at the end of "A Tale of Two Cities" seems like symbolism in terms of being an act of defiance against the system of SC&P.

Bob Benson is Frank Abagnale
The timeline fits. He appeared out of nowhere in season 6 and rapidly rose in the ranks of the firm. His entire appearance was nothing less than a Bavarian Fire Drill, and everybody just assumes someone else hired him.
  • Sort of confirmed. He's not Abagnale, but he's completely unqualified for his job and has been relying on his charm to prevent anyone from finding out.

The show is a novel written by Ken Cosgrove.
He's an award-winning writer who seems to exist on the periphery of the story, yet seems to know everything. Every character on the show has a transgressive double life. Ken's perceived transgression by the rest of the characters at the office is his writing. When he is found out, he goes from writing science fiction stories under one pen name, to writing stories that more resembled literary fiction. In the final episode, it will turn out that everything we see was written by Ken, with his author's voice being someone sort of on the periphery, like Nick in The Great Gatsby.

People who accuse Weiner of creating Glen as a walk-on for his son have it exactly backwards.
He knew all along that he'd want Glen for a few scenes once a season or so. Casting his son who doesn't act in anything else meant he'd have someone who was always available and wouldn't need to find another kid and reintroduce the character with a different actor every time.

Bob Benson is a wolf
The world of Mad Men is not actually the real 1960s but an AU version where a nuclear war breaks out between the US and USSR and the world ends, so Bob Benson is a wolf in disguise who is hanging around Madison Avenue to show people there to Paradise. Pete Campbell is a noble and Bob is pretending to be interested in him in order to keep an eye on him; Pete's mom is, too, and that's why she mysterious disappeared because Bob had to kill he for trying to open an evil version of Paradise. She was just feigning insanity. Also Joan is the Flower Maiden and this is why Bob hangs around her, also why she's so beautiful and every man wants her.

Don Draper is D. B. Cooper
This is a very popular one on the Internet. D. B. Cooper—who used the alias of Dan Cooper—famously hijacked a Boeing 727 on a flight from Portland to Seattle in November 1971, successfully got a $200,000 cash ransom, and parachuted into the wilderness, never to be seen again. He is was described as a dark-haired man in his mid-40s, clean-cut, very well-dressed, very polite, of slightly above-average height, and reasonably decent-looking. The similarities to Don are clear—maybe things really go south for him in 1970-71 and he tries to fix things by disappearing again.

The very final story arc will in some (probably major) way feature the Moon Landing
The final season plays in 1969. The show has always interwoven historical events of the time period with its plot and this is just too perfect to be wasted in some obvious "Let's give all our ad campaigns a space theme!" side story.
  • In his last great act of impersonation Don Draper IS Neil Armstrong!
  • The moon landing takes place during the Season 7A finale, "Waterloo", where it plays a significant role.

Paul's Star Trek script eventually became the episode "Let That Be Your Last Battlefield"
After moving to Hollywood, Paul actually did try submitting his Star Trek script to the show's production staff. Initially it was tossed aside like the piece of crap that it was, but a year later, with the show in the middle of it's infamous third season and in dire need of stories, the production team dusted off Paul's script, rewrote it to eliminate the Hare Krishna elements and change the aliens into "half-whites" and "half-blacks," and then produced it.

Ken Cosgrove will Escape from New York.
Or LA, either works with the show.

The mid-Season 7 finale will be...
Don getting fired for real, possibly for undermining Lou Avery.
  • This almost happened, but Roger managed to save the day. Jim Cutler was the one responsible for it though, not Lou.

Ken isn't blind under the eyepatch.
That's right, he's pulling the old Solid Snake in MGS4 on us. He was crying from it in Season 6. Who knows what's under that patch.


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