Mad Men Speculation: Who the Hell Is James Wolk's Bob Benson?


Assuming you're up to date on Mad Men's sixth season, you may have noticed a new face in the Sterling Cooper Draper Pryce offices. He's kind of hard to miss—dashingly handsome in that squeaky clean all-American way, and the most blatant brown-noser to hit the firm since Pete Campbell's early days. James Wolk (Happy Endings, Lone Star, Political Animals) showed up in the Season 6 premiere as new guy Bob Benson who, honestly, seems to get a lot of screen time for a character who so far has served no apparent function other than being an over-the-top ass-kisser for us to laugh at. Did you know you can even follow him on Twitter?

Theories about Benson abound, though, because the internet loves a good conspiracy theory, and there's nothing like a new Mad Men character to get the lips flapping—or rather, the fingers typing. 

Below, we've compiled some of the most insightful, delightful, and just plain weird Bob Benson theories for your consideration, and added a few of our own. Leave yours in the comments!


FBI Agent

Over on Reddit, there is an entire thread dedicated to theories about brown-nosing Bob. Citing the work SCDP has done with Dow Chemical, past political campaigns, and Don's too-close encounter with the NSA during the American Airlines thing, G-man is one of the out-there-but-not-batshit-crazy theories floating around.


Mad Men Episode IV: A New Hope

Bob recently called SCDP his dream job and said he left his lucrative former gig because it didn't make him happy. Most of the people we've watched grow at the firm—specifically Don, Pete, Joan, and Roger—are pretty miserable there these days. In this past Sunday's "To Have and to Hold," Dawn even remarked that everybody she worked with was always scared, but, you know, Bob never seems scared, and Bob probably should be scared because he always seems to be pissing off someone who's higher than him on the food chain. Peggy escaped to greener pastures because she didn't feel like dealing with the office B.S. anymore. Don hasn't really excelled at his work since Season 4. Roger's been stuck in mid-life crisis mode for at least that long. But despite his sucking up, Benson seems genuinely excited about the opportunities at SCDP, and maybe as Mad Men continues to erode the foundation of the status quo, characters like Bob and Dawn will  prove to be the new breed that leads SCDP into the '70s.


OMG Stop Over-thinking This, He's Just an Overeager Accounts Guy!

Boooooooring. 

But certainly a possibility.



Something Vaguely Villainous

An FBI agent doesn't have to equal a villain. Also, a villain doesn't have to be a world-shaking destroyer of everything you hold dear. Bob Benson's ass-kissing can already be construed as the behavior of a bad guy in that it gives him the appearance of a man who doesn't want to work too hard to move up the ladder, but rather wants to advance by becoming besties with the boss. Maybe Benson's aw-shuck's faux-humility will give way to a more darkly manipulative character once he rises to the level of the very people he keeps trying so hard to impress? Maybe Cosgrove will think twice about pulling rank once Benson is in the position to pull right back? You know, if he makes it that far.

A Long-lost Relative of Ginsberg

We haven't seen much of Ginsberg this season, but the show never returned to his family history after the initial bombshell that he was born in a concentration camp—where his mother died—and later adopted.


Speaking of Long-lost Relatives: Bert's/Roger's/Don's Long-lost Son

While having Benson be the long-lost son of anybody smacks of soap, I admittedly love the idea. 


A Time-traveling Bobby Draper

Because hey, why not?


Just a Regular Guy, But More Importantly: Lady Campbell's Future Lover

Get it, Trudy!

What are your own Bob Benson theories? Let's hear 'em below!

Comments (32)
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He's a ghost.
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He seems like a psycho....and a really really really dangerous psycho given how quiet he is and how he is by chance getting info on everyone's personal lives...Joan and her family problems, Pete and his struggles...Would not be surprised if he holds someone at gunpoint at the end of this season.
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Sociopath.
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Actually, allow me to introduce myself, I am "the" real Bob Benson. Mad Men must have stolen my identity and stuffed me into a part where I am eerie and an ass kisser. Hey, I am cool with that, but my real agenda is residual $, can you dig? If the producers would have found me before this con artist portraying the unique "Bob Benson", the ratings would have jumped DRONE out, well maybe......Like me on Facebook and see you at the Oscars!
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Ok for me Benson is kind of an eerie character given Price's deathly departure. Price's suicide is very clearly still living in the office (and with Don). Something about the fact the Benson is ignored and taken for granted, even though he is earnest and eager, seems reminiscent of Price, am I wrong? Granted Price was more of a grump and not nearly as good looking, I can't shake the feeling that the writers are going to use Benson the same way they used Price, to drive home some kind of lesson about death and to force each character to grow up in their own way (Sterlings mom dying forced him to grow up, Price dying forced everyone to be a little more wise about the companies financials and about their lives - Peggy), and Draper, well he relies on someone dying in the present or a memory of someone dying in the past in order to decide what to have for breakfast) . Back to Benson, as much as the characters were clearly affected by Price's death by suicide, I think Benson will be the vehicle that forces the people of SCDP to stop blithely ignoring what transpired. Why haven't the characters talked about Price yet? What has been done with Price's office? I can't shake the feeling that somehow Benson, who no one seems to be addressing, is somehow or will somehow be connect to Price, who also no one seems to be addressing.
More+
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Perhaps he is one of the "watchers" that Pete mentioned at the partners meeting.
What is distinctly obvious is that everyone from Don to Ken treats him as if he is beneath them somehow. I don't believe he's a real accountant anymore than "Project K" was the actual account name. In some way, they definitely look at him as the enemy.
He's always out in public spaces watching over everyone else and never acutally doing his job in accounts. He's been soundly reprimanded for this several times by different people and it doesn't ruffle a hair on his perfect head - almost like he knows he can't be fired...
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The last scene of the show will reveal Bob staring into a snow globe with SCDP's building in it. Don Draper in construction clothes will ask Bert Cooper "I just don't get it pop, what do you suppose he sees in there?"
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He's the subconscious mind of whomever he's interacting. That's my guess.
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Bob arrived in 1968 in a delorean looking for ways to make the flux capacitor take him back to 1985. Bob Brownnoser is his cover. Only Don knows where Doc is.
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Speaking of Bobby Draper, why does it seem like he's never aged? Sally has.
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I find it suspicous that he's an accounts guy. Wow, isn't everybody? Kind of like saying your job has to do with sales. If I was going to pretend to fit in at SCDP, I'd say yeah I'm in charge of accounts.
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I don't think he's bad, but i do think he's gonna swoop in and take over now that EVERYONE"S personal life is going to shite!
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Exactly.
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And who are the 3 guys working for Peggy?
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Stupidly showed my husband this here article. He's now in the other room looking up Alison Brie's Esquire photos
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Taken directly from the reddit thread itself: "how likely would it be for the FBI to send someone in to infiltrate a young, small, relatively unimportant ad agency?"
Not very, I'd say.

"Bob Benson" is an alliteration, just like "Don Draper", both their first and last names having the same amount of letters. Bob Benson got into the advertising agency by means similar to how Don did. That must mean something!!!1

But seriously, I think he is a "new hope" kind of guy. He said he went to Wharton business school and so far I haven't seen him being late or even so much as holding an alcoholic drink in the office, so that sets him very much apart from ... well, everbody there.


The real question is: Who's going to be shot? MLK, RFK or Warhol?
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The alliteration feels like it's on target, but I think Reddit was too quick to dismiss the FBI agent plot line as we've seen Matthew Weiner bring some really surprising backstories into play before (especially Ginsberg's family history).

I'm rooting for Bob to snitch on some Pete Campbell missteps in order to get ahead... you know Don would be quick to bump Pete from power if he has the means.
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"I'm rooting for Bob to snitch on some Pete Campbell missteps in order to get ahead"

That would be great. It would bring it full circle from when Pete tried to do that to Don.
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--look i don't want to alarm anyone ...but 'Mr Bob' here had some pretty freakin heavy lines in Season 6 premier for example: 'Im Bob Benson,I'm Upstairs, Accounts' (** Don he's "The" **Man from Upstairs** --!!!--- *who holds you ACCOUNTABLE*-- omg! look out DON!) 'Secor,Mohawk, LIFE cereal"... (**Don he's in charge of your LIFE** !!! omg..OMG!) -- 'We spoke at the CHRISTMAS PARTY (*SEE?! some RELIGIOUS stuff!*)--- 'I always get 2, I don't want to share' (**OMG- look out Pete&Ken!!!!!! you may be the '2' he 'gets'...who is he? does he want Ken&Petes soul?..omg), 'I have through lets say 'low-level-corruption' obtained two tickets to the Cotton Bowl' (**'low-level-corruption'** ..omg-- through Satan?Lucifer?..omg?)... .....this is not good----then Bob says: ' i love it down here'..(where? HELL?..omg---a Fallen Angel!--yikes!) :)
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I hope you have a Tumblr that I can read on the reg.
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This review was just so awesome and entertaining. I hope you continue this premise as the episodes progress.
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So you're on board with the FBI agent theory I take it?
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You really have to wonder, because they certainly insert him into the show for seemingly no reason every chance they get. Also, everyone treats him like complete dogsh!t and he takes it all in stride and with a smile on his face. Boring as it sounds, it seems that he's just an ass-kisser who's truly happy to be somewhere other than where his family expects him to be (ye olde accounting firm).
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Bob Benson is an FBI agent who has an affair with Trudy who becomes a corporate spy. When it is found out Pete throws him off the roof thus ending the insider investigation and Pete goes to jail. All of my problems are solved...
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Yessss.
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And I forgot to add Don marries Joan and then becomes Emperor of Earth. From here it gets a bit sci-fi-ey...
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I had it figured out and was going to post the scoop... But I got distracted by the pic of Allison Brie. Now I can't even remember my name :-)
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Ted Chaough's mole. Maybe a surprise rival for a declining Don.

Maybe he turns out to be a brown noser because he went though similar things to Don. He serves as a mirror to Don.
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Corporate Spy
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I bet you he is prob just some random guy. But i think it would be super funny if he was a future Bobby but if that happened then the show wouldnt just jump the shark it would like be jumping a shark with laserbeams attached to its head.
I wouldnt be surprised if Trudy went after him to get back at Pete. if that happens then maybe we could see his long lost rifle again
(also what is with this whole thing about Don getting tossed out of the window thing. Ive always seen the opening sequence as being metaphorical)
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You're right, the opening sequence is probably metaphorical.



Unless it isn't.
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I think I like the Bobby Draper Time traveling theory the best. Seriously though, It has been driving me nuts not knowing. What the hell is this guy up to?
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