Mad Men's Bob Benson: Good Guy, or Some Kind of Spy? View the Evidence and Make the Call

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bob benson mad menWhether Mad Men‘s Bob Benson is an earnest do-gooder or a nefarious weasel is as contentious a debate as whether to sell margarine based on cost or taste.

Though he’s been on the fringe of the action since his introduction in the Season 6 premiere, the new accounts guy (played by James Wolk) is all Mad fans want to talk about. (Well, him and the “Will Megan meet Sharon Tate’s fate?” question.)

Theories on Benson’s true identity – government spy? undercover reporter? Don’s illegitimate son? – abound. And while we’re not yet sure exactly why he’s turned up at Sterling Cooper Draper Pryce Cutler Gleason Chaough Or Whatever They’ll Eventually Call It, we’ve noticed that Benson is a keen observer at life within the firm.

Well, guess what, Bob? We’ve been keeping close tabs on you, too.

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TVLine has monitored the mysterious Mad man’s activities for the season to date, and the gallery below presents his whereabouts in each episode – along with what he appears to be saying/doing in the scene… and what we imagine he’s actually thinking.

We think we’ve caught the big stuff (and most of the small stuff), but the dude is cagey; if we missed any key Bob Benson moment, shout it out in the comments. And while you’re there, make sure to log your thoughts on the ad-agency newbie, as well as any alternate theories on what brings him to Madison Avenue in the late ’60s.

Comments (129)

  • I think he’s Sal’s boyfriend and he’s out (pardon my pun) to settle a score on his behalf.

    Comment by EJ – June 1, 2013 06:33 AM PDT  Reply To This Post
    • Yes. Because that would be utterly fascinating.

      Comment by Lauren – June 1, 2013 06:50 AM PDT  Reply To This Post
    • A lot of the strength found in the theories that Bob is some kind of plant or super villan seems to come from the fact he was phoney about whether his dad was dead or nursed back to perfect health.
      Isn’t it possible he is just a proto-Smithers boot-licker of some kind?

      Comment by Daniel – June 2, 2013 07:22 AM PDT  Reply To This Post
  • Can’t we just have a nice, normal guy on this show for once. LOL Well maybe Ken fits that sometimes. I get how others want to think he’s up to something but I’m tied of all of that. Plus not everyone in this world is so cagey. Just wondering if we all are reading way too much into things. I like James Wolk from when he was on “Political Animals” and I know I’d hate it if Bob turns out to be up to something.

    Comment by Amanda – June 1, 2013 06:47 AM PDT  Reply To This Post
    • This! I really think people are reading too much into this (although with Weiner one never knows). I feel like Bob is basically the chum for these sharks, a contrast to show what people in a less fast-paced and competitive environment are like. As I said to my friend last weekend, “He’s the nice guy who gets eaten alive for doing nothing more than trying to be good to people.” I could be wrong, of course, but I think the theories about the character are a bit extreme compared to what the reality will be.

      Comment by Andromeda – June 1, 2013 07:56 AM PDT  Reply To This Post
      • I think that his comments to Ken about his father dying and then telling Pete how his father has recently been nursed back to perfect health shows he’s not just the nice normal guy. At minimum he’s showing that he will say anything to get ahead whether it’s true or not. Normal on TV is boring. Bob is becoming interesting. And I hope we get to the gist of his being there soon – he’s starring in a new series in the fall with Robin Williams, so he may not be back next year.

        Comment by rowan77 – June 1, 2013 01:24 PM PDT  Reply To This Post
        • Or, could both be true. At one point his father may have been nursed back to health. But he eventually died. It could also be true that he (A) is up to something even if it’s just trying to get in good and play the game AND (B) really does like Joan. Having said that, Mad Men is like Shakespeare: nothing is an accident/incidental.

          Comment by BG – June 2, 2013 01:55 PM PDT  Reply To This Post
          • Both can’t be true. Six months ago (in Mad Men time) Bob’s father was dead. Last week he made it clear that the only reason the nurse was available now was that his father was all better – Do you really think a nurse will wait around for over six months to find work? No, Bob’s up to something. I hope his interest in Joan is real, though. She needs a break in the romance department, and he’s hot.

            Comment by rowan77 – June 2, 2013 08:47 PM PDT  
          • Agree.

            Comment by Gayle Elliott – June 4, 2013 10:25 AM PDT  
          • Bob is disingenuous. Everything he says and does he says and does because he believes it will help him succeed in business. He lied about his father. That’s all. It was a lie of convenience, to help ingratiate himself in the moment. He may actually be a nice, if naive, guy. He’s a believer and a joiner. Right now he has youth, good looks and a sense of white entitlement. He’s not a horrible person but he does have faith in the “natural” order of things. He serves as a contrast to the upheaval in society…playing right outside their doors, down on the street. America belongs to him, so he’s told, if he works hard and follows the rules. But that’s all changing.

            Comment by Kay – June 4, 2013 12:57 PM PDT  
        • There is no next year

          Comment by Coatsie – June 4, 2013 09:57 AM PDT  Reply To This Post
          • They’ve said they’re going into season 7; therefore another season.

            Comment by Gayle Elliott – June 4, 2013 10:25 AM PDT  
        • Whoa whoa whoa!!!! Uhm spoiler alert!!! Serious that kinda proof he’s not coming back – wish I could unread that – stop TELLING people that – sheesh!!!

          Comment by DMH – June 4, 2013 06:10 PM PDT  Reply To This Post
    • Not on this show.

      Comment by Leigh – June 2, 2013 08:55 AM PDT  Reply To This Post
    • True but he can be both and if he is up to something that makes it more exciting! No? It’s not exactly like when Lane was up to something last season and they showed him doing it midway through the season to see it pan out in the end. I have another theory on the spy thing…. Maybe he is investigating Dick Wittman! :)

      Comment by Michael Bueltel – June 4, 2013 10:15 AM PDT  Reply To This Post
  • Nothing could convince me that he’s NOT Don’s illegitimate son. He comments on how much Don knows about Pennsylvania – if teenage Don had a child with Aimee the ‘lady of the night,’ it would have been in Pennsylvania, where he grew up in that whorehouse. He has several stories about his father, which causes none of them to seem honest. Maybe because his real father is Don?? That makes sense to me. I can’t wait to find out if I’m right!

    Comment by mcfly84 – June 1, 2013 06:49 AM PDT  Reply To This Post
    • I’m with you on this one. He looks like Don, he has the same talent at reading people, and, as is Don, he is a good liar. Genetics are not to be underestimated. What could Bob (same name as Don’s son with Betty) have in mind…we shall see.

      Comment by janniel – June 1, 2013 07:44 AM PDT  Reply To This Post
    • Interesting theory. However Don’s real name is Dick Whitman so one would wonder how Bob would have found him as Don Draper.

      Comment by Belle – June 1, 2013 11:27 AM PDT  Reply To This Post
      • Maybe he is the former don draper’s son.

        Comment by vs – June 1, 2013 05:46 PM PDT  Reply To This Post
        • No-not real Don Draper’s son unless real Don Draper got another woman pregnant other than Anna real Don’s wife, whom Dick/Don befriended and took care of-the blond with the bad leg who lived in CA. Could be Dick/Don’s prostitute’s son and Dick/Don’s son and somehow through Dick/Don’s half-brother (who somehow found Dick/Don years ago in the newspaper) or by other means, he found Dick. Benson could have his mom’s last name or his adoptive dad’s name. Or use a fake last name. But I do believe he’s up to something. One minute his dad’s dead; the next a good male nurse has nursed him back to health. And for some reason last week Joan said to Bob that Pete wouldn’t ask Bob for help because he’s too proud. I would think Pete wouldn’t ask Bob because Bob’s not in his radar. But Joan seems to know something we don’t.

          Comment by JMA2Y2 – June 1, 2013 06:24 PM PDT  Reply To This Post
        • my thoughts exactly! Son of the real Don Draper!

          Comment by Melanie Thompson – June 4, 2013 02:44 PM PDT  Reply To This Post
    • Don is from the Midwest. Did they travel to PA; missed that.

      Comment by Gayle Elliott – June 4, 2013 10:27 AM PDT  Reply To This Post
    • i agree!

      Comment by Michele – June 4, 2013 12:16 PM PDT  Reply To This Post
  • I think he’s a weasely ladder-climber who tries to ingratiate himself and get a lot of dirt to gain power. Or perhaps he is Matt Weiner’s version of J. Pierpont Finch, in which case they are building to a major smack down scene with Bert Cooper schooling him and firing him in the ultimate oh wow moment: the real Finch taking down the wannabe.

    Comment by Ann – June 1, 2013 07:17 AM PDT  Reply To This Post
    • Awesome theory! I really think he’s Don Part 2, not his son, just the new generation of ambitious, handsome, smooth ladder climber. J. Pierrepont Finch works, too, though, especially with Burt/Ponty himself in the office.

      Comment by Julie – June 1, 2013 01:41 PM PDT  Reply To This Post
      • Ooooh I like this theory! An homage to J. Pierpont himself!

        What has always seemed odd to me is that Benson says he’s “in Accounts, upstairs.” But as Roger Sterling asked him last Sunday, “Why are you always down here? Go back upstairs where you belong!” There’s one scene last Sunday with Bob answering “his” phone – but the desk and surrounding area looks to be terribly generic. Are we *sure* he works upstairs in Accounts? Are we *sure* he even works there at all? What if he’s borrowed a page from “How to Succeed” and is working for “a company that is so large no one know exactly what the other person is doing.” Maybe Bob Benson is really a window-washer who, like Finch wanted to be on the inside.

        Comment by Delia – June 4, 2013 11:13 AM PDT  Reply To This Post
    • I have no idea where they’re taking this with Bob, but I kind of learn toward your theory that he’s just an extremely ambitious ladder-climber. I’m waiting for him to get someone fired so that he can move up in the company or else get some prime dirt on a partner that gets him promoted.

      Comment by Britta Unfiltered – June 1, 2013 02:54 PM PDT  Reply To This Post
  • He seems to have that Greek coffee cup in his hand a lot…

    Comment by PJ – June 1, 2013 07:45 AM PDT  Reply To This Post
    • He usually has 2, and if memory serves me correctly, in the beginning Don gets in with Roger by having and extra cup of coffee for him while he is nursing a hangover. I can’t remember the episode.

      Comment by Eric – June 4, 2013 10:23 AM PDT  Reply To This Post
      • Good catch!

        Comment by Gayle Elliott – June 4, 2013 10:31 AM PDT  Reply To This Post
    • “Beware of Greeks bearing gifts.”

      Comment by JoanLookAlike – June 4, 2013 10:24 AM PDT  Reply To This Post
  • I wouldn’t put it past Wiener to have a mostly innocuous, nice guy on the show just to play off the fans’ paranoia and reading into things.

    That said, he is totally Don’s son!

    Comment by Dryden – June 1, 2013 07:45 AM PDT  Reply To This Post
  • Don’t know if James Wolk is leaving Mad Men after the end of the season now that he’s off doing his new sitcom The Crazy Ones over on CBS.

    Comment by Jack Bauer 2.0 – June 1, 2013 08:04 AM PDT  Reply To This Post
    • I thought this was the last season of Mad Men.

      Comment by Deborah Morrow (@DebbyMorrow) – June 1, 2013 08:30 AM PDT  Reply To This Post
      • Next season is the last.

        Comment by Don – June 1, 2013 09:52 AM PDT  Reply To This Post
    • Since he doesn’t have that big of a role on Mad Men, he may be able to film both shows next spring, a la Alison Brie.

      Comment by JC – June 1, 2013 01:08 PM PDT  Reply To This Post
  • First, can’t stand this guy. No matter the role he can’t wipe that constant smirk off his face and it ruins his characters. Be serious for once. Second, I guess his character is a cop or some sort of investigator looking into the company after what Lane did and his ultimate suicide. He seems to be buttering people up for info and has no real job other than that and handing out coffee.

    Comment by ajintexas – June 1, 2013 08:08 AM PDT  Reply To This Post
    • This makes sense to me……or he might be from the IRS, or possibly a spy from another big ad agency looking for “secrets”.

      Comment by Nancy – June 1, 2013 09:17 AM PDT  Reply To This Post
      • I almost wrote spying for another ad agency. People might want to know how Don does what he does. The IRS is good, or even some other Fed. Sometimes even I forget Don Draper is a fake identity after all.

        Comment by ajintexas – June 1, 2013 02:22 PM PDT  Reply To This Post
        • If he’s there to steal secrets, they should have sent in a creative, not a salesman. The creatives meet and work with Don. The sales guys work with Pete. I think this may be more about Pete than Don. Although being Don’s son is an intriguing idea.

          Comment by Rowan77 – June 2, 2013 06:42 AM PDT  Reply To This Post
      • I think he may be a g-man, sent to uncover the real identity of don draper. Remember, don/dick made a fortune in the sale of SC during season 2, which would motivate the IRS. Bob could be acting very kindly to Pete for 2 reasons. First, Pete knows that don is really Dick Whitman, and Pete has a friend, Russ (?) at the DOD. Perhaps Russ is the one who sent Bob, and Bob knows he needs to get close to Pete.

        Comment by Cheri – June 8, 2013 03:41 PM PDT  Reply To This Post
    • Bob’s character is very real, even in 2013. I work with people like him.

      Comment by Belle – June 1, 2013 11:29 AM PDT  Reply To This Post
      • Bob does not work at the agency. There is no way anyone in advertising would ever hire anyone like him in any department. He is just too normal, plain, boring. Especially in an agency like Sterling Cooper. No one would ever say they work “in accounts.” Mad Men usually gets it right, so this seems to be an intentional “error” rather than a writer’s oversight in ad terms. There is “account service” and ” accounting” but not “accounts.” He has no role. The dude is not really employed there. He has somehow managed to float in as a pretender, and for some reason Joan may know and be keeping the secret. Don’s son? That’s way to easy. I doubt it. I find him highly annoying and he doesn’t fit in the show, just like he doesn’t fit in the agency! So there has to be a reason. But what?

        Comment by AdGirl – June 4, 2013 08:06 PM PDT  Reply To This Post
        • Bob does work there. Didn’t Joan save his job right when they were going to ax him? He had just taken her to the hospital and performed his sweet talking magic and Joan saves his job. How would he be in the fire list if he didn’t work there?

          Agree there is something up with him but believe the Don using coffee for Cooper to get his job connection is right on. His lying and sucking up seem to just point to the same qualities in Don’s and his ability to say or do anything necessary to get what he wants.

          Likely there is more to the story but an unknown son? Seems to soap opera-Ish for Weiner. Couldn’t he be the younger Don without having to actually be related to make the point?

          Comment by Jennifer – June 9, 2013 09:08 PM PDT  Reply To This Post
  • As much as I am enjoying the commentary on Bob and love James Wolk, what does this say about the season if THIS is the most interesting thing to talk about? No real chatter on the Don/Peggy/Ted triangle. Don is being an ass, again. Roger is feeling sorry for himself, again. Peter can’t figure out why people won’t respect him, again. If it wasn’t for Bob or dare I say Megan, Mad Men wouldn’t have much to talk about.

    Comment by DramaMomma – June 1, 2013 08:33 AM PDT  Reply To This Post
    • Megan’s never been interesting to me. She’s a tantrum-throwing, selfish child who married the wrong man. And she gets hit on a lot by her show-within-a-show co star. With Megan what you see is what you get. Meh. Bob has a secret and a strategy. And he’s cute as hell.

      Comment by Rowan77 – June 2, 2013 06:49 AM PDT  Reply To This Post
      • Regarding your comments about Megan. You took the words right out of mouth. Honestly, I just can’t stand her – character and she is certainly is not a trophy wife. Obviously this marriage was doomed from the start and kept getting more bizarre with every episode. Remember the Howard Johnson trip? I still don’t know where she went … Then the birthday gift ( that embarrassing song she sang to Don). Ugh. I say goodbye Megan and get set for another divorce – don will go broke.

        Comment by Sandi Bittinger – June 21, 2013 03:55 PM PDT  Reply To This Post
  • It never crossed my mind that he could be Don’s long lost child, this season I think the most interesting person is Don’s daughter this was the late 60′s and she could go anywhere with her part.

    Comment by Liz Feeser-Regan – June 1, 2013 08:50 AM PDT  Reply To This Post
  • I think his turning out to be Don’s son is a typical soap opera cliche which this show is but at a higher level. Just as I’d love for Megan to run off with Harry Hamlin. Also, not to be nit-picky, but what happened to all of Betty’s loose skin from losing a ton of weight? If only it were that easy. My fave touch in the series was Sally reading Rosemary’s baby. Classic.

    Comment by asta – June 1, 2013 09:16 AM PDT  Reply To This Post
    • Not everyone has loose skin from weight loss. Some people tone it up as they lose weight through exercise. Some people are just genetically predisposed to not be stuck with the flab.

      Comment by TV Gord – June 1, 2013 09:58 AM PDT  Reply To This Post
    • I agree, it’s way too soapy of a direction to go for this show.

      Comment by Britta Unfiltered – June 1, 2013 02:59 PM PDT  Reply To This Post
      • It might be too soapy an idea but isn’t there a soap-within-a-show right now on Mad Men with To Have And To Hold? A revelation such as Bob’s being Don’s long-lost son would serve as a highly ironic counterpoint to that.

        Comment by EJ – June 1, 2013 04:11 PM PDT  Reply To This Post
        • They would do that quite often, and brilliantly on Twin Peaks with a fictional soap-within-the-show called ” Invitation to Love” that would often mirror the soapy plot devices in Twin Peaks (like the deceased Laura Palmer (Sheryl Lee)’s cousin with an uncanny resemblance, Maddy (Sheryl Lee).

          Comment by Peter James – June 2, 2013 02:05 AM PDT  Reply To This Post
  • This season “Mad Men” is just not progressing…..I lived in the 60s, worked for an ad agency in L.A. These were some of the most exciting times in our history, and the series needs to be affected more by the changes in our society, and focus less on Don alone.

    Comment by Nancy – June 1, 2013 09:21 AM PDT  Reply To This Post
    • Thank you, Nancy! My thoughts exactly! Even though I was around Sally Drapers age in the 60′s that era had permeated every aspect of life, They nailed the cultural impact in the first season. After that it might as well be 1999.

      Comment by Laurie S. – June 9, 2013 08:03 PM PDT  Reply To This Post
  • After Mad Men is over Bob should go to NBC because for me he looks a lot like Nick on Grimm, he could play his long lost (I never knew I had a brother) on the show..LOL!!!!

    Comment by K. – June 1, 2013 09:29 AM PDT  Reply To This Post
  • I don’t care what anyone says, it’s still one of the best shows ever!

    Comment by Linda – June 1, 2013 09:30 AM PDT  Reply To This Post
    • Agree!

      Comment by janniel – June 1, 2013 09:33 AM PDT  Reply To This Post
      • Thanks for saying that. I think so, too!

        Comment by TV Gord – June 1, 2013 09:59 AM PDT  Reply To This Post
  • Don’s illegitimate son from Aimee? I don’t think so. Don was not Don Draper back then. Records would say Benson’s father was killed in Korea.

    Comment by MG – June 1, 2013 09:45 AM PDT  Reply To This Post
  • I think he’s in cahoots with Grandma Ida !

    Comment by James Hawley – June 1, 2013 09:51 AM PDT  Reply To This Post
    • Or not. I don’t think he is as important as you keep trying to point out. A lot of people lie about the dumbest things. If it fits the moment, they just make up something to add to the conversation or make themselves look good. If he is an agent of some sort, I will be impressed by the guesses here.

      Comment by cerelon – June 2, 2013 04:16 AM PDT  Reply To This Post
    • Best comment yet!

      Comment by Libby Franck – June 4, 2013 10:54 AM PDT  Reply To This Post
  • He obviously tries to kiss butt all the time and he has lied to both Ken and Pete about things to try and justify his actions. First his dad is dead and he would appreciate any gesture then his father has been nursed back to health by the “well-bred” male nurse. Notice it is a male nurse. How many of those were there in 1968? Could it be a colleague in whatever he is in bed with? Even gay men would love to get a gander at Joan’s amazing assets.

    Comment by richerdz – June 1, 2013 09:58 AM PDT  Reply To This Post
  • How about a bastard son of Bert’s? The black sheep son, come to claim his place in the kingdom.

    He’s actively sucked up to everyone but Bert. Maybe he hasn’t been so much sucking up as taking the measure of what will be future rivals or allies, once he reveals himself.

    Those who treat him well now could gain favor, and those who blow him off could find that this ‘nice guy’ has a long memory and very sharp claws.

    Comment by JMill – June 1, 2013 10:31 AM PDT  Reply To This Post
    • Couldn’t be, Bert was castrated by an incompetent doctor long before Bob was born. That was revealed in Season 4 I believe.

      Comment by BabyLawyer – June 4, 2013 10:09 AM PDT  Reply To This Post
  • Who knows, with Weiner holding all his cards so close to the vest. No one knows the guy, so apparently no one hired him. I wouldn’t be surprised to see Joan be the one to break the case by simply checking to see if Bob has ever even drawn a paycheck.

    Comment by Cheo – June 1, 2013 12:30 PM PDT  Reply To This Post
  • I think he’s that kind of nice guy that could snap in a moment and his snap will turn him down a dark (murderous?) path.

    Comment by Sarah – June 1, 2013 12:39 PM PDT  Reply To This Post
  • Maybe Bob is a paralell to an earlier version of Don, rather than his illegitimate son. In an earlier season, there’s a flashback to when Don was first hired by Roger. Don has the same countenance as Bob Bensen for those flashbacks . The ironic thing is that Roger is unsure when Don shows up for his first day of work whether he actually hired Don. It is slightly inferred that Don just started showing up and he got himself the job by being around (okay this might be a slight exaggeration). Do we ever really see Bob do any work? Bob, at least to me, is appearing as if he is hanging around, getting to know people and will maybe replace Don in a symbolic sense. It would kind of go along with this theme of Don being disconnected from the current, free, younger generation( i.e. Meg’s generation, Peggy’s generation, Ginsberg’s(if I spelled that wrong please feel free to correct) generation,etc.).

    Comment by Emma – June 1, 2013 02:14 PM PDT  Reply To This Post
    • My theory is that he is an undercover journalist, investigating the advertising world in the ’60s. Simply because he ‘just shows up’ and seems to fit in, no one questions him, he doesn’t seem to report to anyone. What is going to come out of his time at the agency is a ‘best seller’ on advertising or an investigative piece for the NY Times, WSJ or some major newspaper. After all this is also the era of Woodward and Bernstein.

      Comment by cathy – June 4, 2013 10:16 AM PDT  Reply To This Post
  • I can’t say I really believe this, but it has crossed my mind that Bob might be a dangerous guy. All the speculation about Megan/Sharon Tate made me think of serial killers like Manson and Ted Bundy, the former of whom was considered attractive and fairly successful (and is speculated to have begun killing around 1968/9). I really have nothing here, except that Bob seemingly lied about his father and the fact that murder, or at least more violence, is being foreshadowed pretty heavily. So maybe the mystery surrounding Bob and the Tate references are not unrelated.

    Comment by Dillon – June 1, 2013 04:02 PM PDT  Reply To This Post
    • Oh dear. And there is now a ‘Ted’ on Mad Men. lol

      Comment by Angie – June 2, 2013 05:54 AM PDT  Reply To This Post
  • There’s a scene in ep9, “The Better Half”, where Don and Betty visit Bobby at camp and Bobby, played by Mason Cotton Vale, says he’s Bobby 5, which is almost true because three other boys have played Don’s son, Bobby before him. Then he says, Bobby 1 left. That could mean Bobby 1 is Don’s first son, who we haven’t seen yet. Bob Benson? Or maybe it could mean Megan’s aborted son.

    On the other hand, Bob Benson is always holding and handing out those coffee cups, as someone here pointed out. They could be bugged for an FBI investigation.

    And who knows, both theories could be related. Or both a red herring. Anyway. It’s a good show.

    Comment by APrime – June 1, 2013 06:43 PM PDT  Reply To This Post
    • Bugged paper coffee cups in the 1960s? LOL! Bugs back then were huge, so you’d see them easily. Plus they aren’t waterproof so if you try hide them in the coffee they would short out and be seen as people drink. Funny idea though.

      Comment by Rowan77 – June 2, 2013 06:59 AM PDT  Reply To This Post
      • Beware the FBI agent who hands you a cup of coffee, especially if they light your cigarette, the lighter or matches back in the day were used as a distraction to drop a pill into the drink.

        Comment by Gayle Elliott – June 4, 2013 10:39 AM PDT  Reply To This Post
    • I had completely forgotten about Bobby saying he was #5. I wonder what that really means??

      Comment by Angie Lockhart – June 4, 2013 01:15 PM PDT  Reply To This Post
      • Bobby 5 just meant there were five campers named Bobby.

        Comment by Carlene Przykucki – June 6, 2013 05:12 AM PDT  Reply To This Post
  • The Megan getting murdered theory is completely ridiculous. And Bob is nothing but an ambitious career climber. Mad Men fans have too much time on their hands it seems!

    The best thing that has happened this season was the hot Don/Betty hook up and the talk they had afterwards.

    Comment by ca – June 1, 2013 07:50 PM PDT  Reply To This Post
    • Mad Men fans have at least enough time to be Mad Men fans, a show that’s full of subtle under tones. I wouldn’t count it’s fandom and the small devotion of time on all it’s various moving parts and pieces as a detriment or even a waste. It’s playful speculation, nothing more.

      Comment by FlapJoy (@KingFlapJoy) – June 4, 2013 10:33 AM PDT  Reply To This Post
  • I just think he’s trying to get a job. However I bet that it turns out that he’s not that nice of a guy and I betting he turns out to be so backstabbing and conniving that he puts Pete Campbell from Season’s 1 and 2 to shame. I bet Joan falls for him and he ends up using her to get himself a nice, secure and coushy job at the firm.

    Comment by Patrick Snell – June 1, 2013 08:16 PM PDT  Reply To This Post
  • I have no idea what all this means! But it would be nice for Joan to have a boyfriend/husband that cared for her and wasn’t a jerk.

    Comment by bobbie – June 1, 2013 10:56 PM PDT  Reply To This Post
    • Sometimes I wonder if them not allowing Joan to have a ‘good man’ is a kind of punishment for her being so beautiful and the object of every mans fantasy. Most women on the show admire Joan & wish they were her but they don’t see that everything she has or had either didn’t work out I.e. her marriage to Kevin…or she had to do vile things to get sleeping w/the Jaguar guy to make partner. I’d love to see her with someone who will truly love her…I’m secretly still hoping for Roger & Joan to get back together & go public with it. Hey I can dream right? ;)

      Comment by Angie Lockhart – June 4, 2013 01:31 PM PDT  Reply To This Post
  • Bob is all style and no substance. He’s completely aware of his image to others as a
    charming, helpful and clean-cut guy, and he uses it. But there’s nobody home. In tonight’s
    episode (“Tale of Two Cities”) he’s not at all pleased that Jim has thrown him into the lion’s cage with the Manischewitz account. He’s actually in a panic – though he hides it — when he learns that Michael is trying to get out of the meeting and uses his Dale Carnegie technique to successfully talk Ginzburg back into going. But his abilities as an account exec are exposed when he comes back with the news that the meeting was a bust and the firm will lose Manischewitz. However he’s already managed to win over Jim — not too birght himself — who wishes to pack the office with “his” people. He’s an extremely dangerous member of the that office and will probably wreak havoc before he’s finally found out.

    Comment by Jerry – June 2, 2013 09:44 PM PDT  Reply To This Post
    • Very well said, Jerry!

      Comment by Susan – June 4, 2013 10:05 AM PDT  Reply To This Post
  • Maybe Bob is a sociopath… perhaps even a serial killer. Nice guy, studies people while being somewhat unassuming. This season they talk a lot about the various grizzly killings that were happening in that era, the “Nurses” are brought up quit a bit. The odd crimes going on, like the lady who broke into Don’s apartment. Maybe Bob is the one that kills Megan, combining both show rumors in one arc.

    Comment by FlapJoy (@KingFlapJoy) – June 4, 2013 09:58 AM PDT  Reply To This Post
  • Not a truly nice guy,(though it would have been nice for Joan), because a truly nice guy wouldn’t have offered to pay for Pete’s hooker/lied about his dad’s death; and a nice guy would have friends/places to go other than work. He’s like a younger version of Don, a sociopath. I think at the end he’ll either lead to the firm or Don’s downfall, or be extremely violent in some way as others have suggested. AAAH! Speculating is my favorite part of watching the show!

    Comment by Margaret Dilloway (@mdilloway) – June 4, 2013 09:58 AM PDT  Reply To This Post
  • Anyone remember when Bob was first introduced? Wasn’t in an elevator and Don had no idea who he was? Have we even seen Bob working on anything in accounts? The only time we see him is when he’s just randomly moseying around the creative department.

    Isn’t there a chance that Bob doesn’t even work at the agency, and he’s just been pretending to work there, and everyone in the company is just too busy (or drunk) to realize he’s not even part of the company? This makes me think he’s some sort of spy, and he’s just gotten really lucky to have gotten so far.

    Comment by nicktat – June 4, 2013 10:01 AM PDT  Reply To This Post
    • Well, he was almost let go after the merger, until Joan saved him… so, he must be on the SCDP roster on some level.

      Comment by FlapJoy (@KingFlapJoy) – June 4, 2013 10:28 AM PDT  Reply To This Post
  • I think he represents the new school. He doesn’t drink but offers to buy them, most likely graduated college but isn’t going to just jump in the dirtiness which is advertising, he remains ignorant of all past wrongs and attempts to stay clear away from new ones being committed. He is the change of generation from don, roger, and Pete.

    Comment by Keenan – June 4, 2013 10:07 AM PDT  Reply To This Post
  • How come no one’s mentioned the fact that Bob Benson had to psych himself up before a meeting with a motivational record? That’s got to infer some sort of mental instability right? As confident as he appears, he’s really not that person naturally.

    Comment by Simon – June 4, 2013 10:07 AM PDT  Reply To This Post
    • Millions of people read the book “How to win friends and Influence people”, same kind of thing. Doesn’t mean he’s unstable, tells me more about his focus, he wants to succeed… that ain’t crazy.

      Comment by FlapJoy (@KingFlapJoy) – June 4, 2013 10:37 AM PDT  Reply To This Post
  • Judging from the season 6 poster (a sketch featuring 2 Dons, or 2 halves of the same person) and all that has transpired in S6, this season has been about all the faces of Don or even the archetypes that make up his character. I think many characters are meant to represent these pieces of Don. In Peggy we see the professional dynamo side, in Pete we see the adulterer/home wrecker, plus think about Betty, Megan, and Sylvia all representing certain female archtypes that reflect what he wants and/or needs. I think it’s also notable that 2 agencies joined together and that there is friction between Don and Ted, who are basically the same person for each agency (reflections, have you). I have a suspicion that Bob plays a part in this – perhaps the future Don? I think the “5 Bobbys” mentioned by little Bobby at camp is also a notable hint. Mad Men is full of subtle meanings or signs/symbolism, sometimes they mean something, sometimes then don’t…why I love this show!

    Comment by K8E – June 4, 2013 10:09 AM PDT  Reply To This Post
    • Very good theory! Also, Bobby Kennedy is mentioned. And we know what’s coming there.

      Comment by Gayle Elliott – June 4, 2013 10:46 AM PDT  Reply To This Post
    • I think K8E is on the right track. This show is all about Don foremost !

      Comment by ann turner – June 4, 2013 11:02 AM PDT  Reply To This Post
  • Dang. All interesting theories. Weiner has misled his audience before (Peggy’s son, as her nephew, maybe). With Megan in a soap opera, I wouldn’t be surprised if MW pulls a big reveal at the end. Trying not to over analyze too much …. it has been fun to speculate BB’s motives all season!

    Comment by Retro Wife (@retrowife63) – June 4, 2013 10:14 AM PDT  Reply To This Post
  • It’s really simple
    Bob is a private detective hired by the Widow of Layne Pryce to dig up dirt and ruin the people she feels murdered her husband. She’s paying him the 10,000 that the firm gave her.
    He’s sucking up to Pete because Pete and Don clash often and loudly in the office. Knowing that Pete will eventually blow his top and lose control of his mouth Bob is just pushing for the big reveal.
    He’s going to find out Don isn’t Don
    He’s also cultivating Joan because she is the partner closest to the books and if the Widow were planning a raid or lawsuit she would want to know the assets of the firm. Also she might want info on exactly how Joan became a partner which was in a technical sense illegal ( IE Prostitution) which might also be used in court or in getting people arrested.

    Comment by Gillbill – June 4, 2013 10:34 AM PDT  Reply To This Post
    • Good theory

      Comment by Gayle Elliott – June 4, 2013 10:57 AM PDT  Reply To This Post
  • I think if you have worked in a big agency, like I have you realize. He is just a kiss up who wants to make his way up the food chain. There are so many people like that in large agencies, it ridiculous. He is going to end up being Joans new man, and her Pete and Bob will start makin’ moves.

    Comment by Superman – June 4, 2013 10:39 AM PDT  Reply To This Post
  • Didn’t they decide on naming it Roger Sterling and partners?

    Comment by Cean Carter – June 4, 2013 10:39 AM PDT  Reply To This Post
    • Sterling Cooper & Partners

      Comment by Simon – June 4, 2013 10:54 AM PDT  Reply To This Post
  • He’s the new Don Draper…pretty, slick, and knows how to schmooz. He will take over much as Don did.

    Comment by Kathy – June 4, 2013 10:43 AM PDT  Reply To This Post
    • Nah..Bob doesn’t have the native intelligence of Don. He’s bright but he’s not brilliant.

      Comment by Kay – June 4, 2013 01:00 PM PDT  Reply To This Post
  • He’s CIA; the agency planted people in ad agencies all the time. And this is a time of all sorts of stuff going on the the U.S. Gov’t. Bob may be scoping them out to find out whether they are trustworthy enough to handle gov’t business and needs to know what everyone’s Achilles Heel is because that could compromise them.

    Comment by Leslie – June 4, 2013 10:45 AM PDT  Reply To This Post
  • Last episode when Cutler was arguing with Ginsberg, he yelled at Benson when he interjected himself into the conversation asking “Why are you always down here!? Get back to work!” because as an accounts man he should be upstairs not in creative….so yes why is he always down there, just floating around, never seeming to be working….the photo posted in this article of when he set up shop on the random table…I never thought about that but I definitely think it’s because he doesn’t have a real work space. Spy, Fed, or whatever…he is up to something. Honestly if he isn’t…how utterly boring.

    Comment by LD – June 4, 2013 10:46 AM PDT  Reply To This Post
  • From a practical standpoint (as others have hinted in the comments) shows like this are always in danger of getting “too dark.” So it does help to have a (seemingly) nice guy around, when everyone else is jealous or provoked.
    Then again, you have to acknowledge some of the characters have a “symbolic” identity, in addition to their “face value.” To me, a character that descends a staircase from up above the show’s office set (into the “real world” of the show, from a realm we’ve never seen), announcing himself as being “upstairs in accounts,” is symbolic of some Heavenly angel of Judgment Day– which will also feed into the teasing speculation that he could “snap at any moment.”
    But, to me, that explains why he’s so insistent about finding out and getting involved and observing. And his seemingly stunned reaction this past Sunday, when the Jewish ad guy says, “tell me the truth– are you a homo?” I almost don’t think Bob has a sexual identity (yet). This may change, he may become more of a regular character, but initially, he does seem almost impossibly angelic.

    Comment by Richard63104 – June 4, 2013 10:58 AM PDT  Reply To This Post
  • He’s got Mormon written all over him.

    Comment by kim (@xokhr) – June 4, 2013 11:05 AM PDT  Reply To This Post
    • If he starts singing “I Believe” from Book of Mormon it will be the single best moment on TV ever.

      Comment by rowan77 – June 4, 2013 11:21 AM PDT  Reply To This Post
    • I thought that exactly. There are a lot of Mormons in the FBI, etc. because of their supposed trustworthiness.

      Comment by Gayle Elliott – June 4, 2013 11:24 AM PDT  Reply To This Post
    • I don’t think Mormons can have caffeine…

      Comment by pam – June 4, 2013 11:53 AM PDT  Reply To This Post
      • I thought they had the Sanka account.

        Comment by lulm – June 5, 2013 01:19 AM PDT  Reply To This Post
      • You are right about the caffeine–I used to be a Mormon. Maybe it is the perfect cover–maybe it’s Sanka in his cup (person below this comment mentioned Sanka), real coffee in the other person’s cup.

        Comment by Gayle Elliott – June 5, 2013 08:57 AM PDT  Reply To This Post
  • I don’t think the IRS or the FBI would have the remotest possible interest in Sterling Cooper. What has anyone done wrong there? And I doubt a journalist would go undercover for months there. What investigation would warrant that big an expenditure (i.e. a salaried journalist not producing any other copy for months) and why would an ad agency be the target for that skullduggery? I don’t think Benson is Don’s illegitimate son via the hooker. Don is early 40s – the zoobie zoobie zoo episode was his 40th birthday party, I think, and in calendar time it’s a year or two previously – and Benson is old enough to make it barely mathematically possible. But also, he seems pretty well-bred, a lot more likely to have been the son of people with BBH for three generations than the out of wedlock son of a small-town hooker. It is interesting, though, that there’s been so little explanation of what he does there, who hired him, where he came from. Should we conclude he’s now banging Joan, lucky devil? I was unclear form the context where she and he were headed for an overnight, bang-positive trip to the beach sans kids – or a day trip, maybe with the baby in tow, and he does already have his swimsuit on, less likely to be bang-positive. I don’t see Joan as being interested in someone just out of college, Benson is probably a little older than that.

    Comment by Danno – June 4, 2013 11:13 AM PDT  Reply To This Post
  • If Joan is the office manager/partner in the firm, then I think she would know who he is and what his job is, don’t you think? That doesn’t mean he didn’t lie to get in there. Don’s son, corporate spy, government spy, or just a regular weasel? Also, I wonder why the heck he always gets outside coffee when they already have coffee in the office kitchen. And he’s always walking around with it. Whatever, he’s too weird for me even if he is good looking.

    Comment by pam – June 4, 2013 11:51 AM PDT  Reply To This Post
  • So, what is behind Bob Benson’s facial expressions will tell it all. Here are the keys. THE SINCERE SMILE-  As pleasant as a clergyman, which he was before he dropped out of priesthood.  Still altruistic, but horny.  KIND TO EVERYONE – because he has 18 months to live.  And in a  future plot  twist, modern medicine finds the cure after Joan agrees to fulfill his dream of leaving a child behind when he “dies”.  Joan stabs him with a hot poker when he survives.  QUIET CONFIDENCE – because he is secretly Bert Cooper’s love toy, and is the sole beneficiary of the old man’s will, which makes him a full partner when Bert chokes to death on ancient wine salvaged from the wreck of a pre-Christian Etruscan trader at the bottom of the Med. Bob is kind, nice, and confident that he is going to be the boss of all these people someday.

    Comment by athomeatfenway – June 4, 2013 12:14 PM PDT  Reply To This Post
  • I think if he’s up to something sinister, it has to do with either the money or info that Joan has access to, or Pete. If you look at how the agency evolved, in the beginning, Sterling Cooper was mostly WASPs. Now they’re all gone from Don’s team, but they still control the accounts department — those ‘elite’ family / social / school connections were necessary to bring in and maintain business, but now that’s changing. Ken doesn’t want to use his family connections, being a WASP isn’t helping Roger any more (look at how he was dressed when he got punched in the balls by hippie Danny!), and Pete’s family is now his biggest liability. Plus Joan just proved that someone of a lower social class can get a meeting with a Fortune 500 company. Bob’s secret might just be that he’s a merciless social climber, like a young Great Gatsby.

    Comment by dandy – June 4, 2013 12:30 PM PDT  Reply To This Post
  • The fact that Bob was listening to a how-to-succeed-in-business record and later, when Ginsberg was having a panic attack, regurgitated the same sort of motivational-speak to help him through it makes me think Bob is just a naive, optimistic, mid 20th-century white guy trying to lasso the American Dream. 35 years from now he’ll lose his job, his pension, his savings and his house. All because he did what he was supposed to do.

    Comment by Kay – June 4, 2013 12:35 PM PDT  Reply To This Post
  • He’s Ida and Burt’s grandson…

    Comment by Sarge – June 4, 2013 12:57 PM PDT  Reply To This Post
  • After reading through a lot of these excellent theories, the most gripping and compelling is Mr. Benson being a G-man on Dons fake identity trail. That would be awesome!

    Comment by BigCity67 – June 4, 2013 02:08 PM PDT  Reply To This Post
    • I think that huge part of the show is behind us. I don’t even think it matters anymore?

      Comment by Gailer – June 4, 2013 06:28 PM PDT  Reply To This Post
  • Bob’s a comer at the outset of his career. Anyone remember how Don Draper got his start at Sterling Cooper? Bob’s the account-side equivalent; bold ambition tempered perhaps by the nice guy persona. The nice guy part makes him more like the anti-Pete Campbell.

    Comment by Art – June 4, 2013 03:23 PM PDT  Reply To This Post
    • Agree. Bon mirrors Don’a behavior but he seems to be less conflicted and therefore has less vices. Kind of like many in today’s society. Same immoral or amoral conduct today as our elders but with less of a conscious or guilt and so less.

      Greed is good was not solely an eighties phenomenon. Weiner may be simply making larger points about society.

      Bob seems to be the only one who is not affected by the external world’s undoing. He haut floats along holding his two coffee cups and a strange grin on his face.

      Comment by Jennifer – June 9, 2013 09:13 PM PDT  Reply To This Post

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