Because of the intense mystery and interest surrounding Bob Benson in Season 6 of Mad Men, I put together this chronicle. Here is everything we know about Bob Benson, based on his appearances in Season 6 and 7 of Mad Men.
Bob does not appear in episodes 6.05 (The Flood) or 6.08 (The Crash).
6.01: The Doorway Part 1
He enters the elevator with two coffee cups and starts schmoozing Don. He says he went to Beloit College, has a Wharton MBA, and is from Pennsylvania. He nakedly tries to butter up Don, and offers to give him Cotton Bowl tickets.
Later, Pete takes the second coffee cup from Bob’s hand. About the coffee, Bob says “I always get two. I don’t wanna to share.” But he gave Don one and Pete knew without asking that the other was for him.
6.02: The Doorway Part 2
Bob sends food to Mrs. Sterling’s funeral. When Ken confronts Bob about this, Bob references when “My father died.”
6.03: The Collaborators:
Bob says he was with Brown Brothers Harriman for a year, and his family had been there for three generations.
6.04: To Have and To Hold
He’s hanging around the creative lounge, drinking his own coffee.
6.06: For Immediate Release
He appears four times. First, Pete sends him for ice. Next, Pete celebrates in a brothel. We see Bob loitering in the hall (not with a girl) and asking if he can pay for Pete. The next day he has two coffees, and offers Pete one. Finally, when Pete starts screaming at Don, everyone comes to gawk, including Bob on the stairs. When Joan ushers the partners into the conference room, Bob leans in to see if he can continue to listen.
6.07: Man with a Plan
He greets Burt Peterson, saying he’s supposed to report to him.
Later, Bob goes into Joan’s office with paperwork. He finds her sick and distressed, with sharp pains and apparently vomiting. He suggests appendicitis but it’s on her left side. She doesn’t want to leave and have everyone see her. He tells her he’ll get her out the door by acting like he’s bothering her.
In the emergency room, Bob brings Joan a soda. He’s called home for her and gotten the babysitter to stay, but he’s staying with her because they can’t reach her mother. Joan is paler and starts talking about dying. Bob takes her to the desk, where the nurse doesn’t bother to look up, telling them they should wait. Bob makes up a story about Joan drinking furniture polish, which gets Joan immediate attention, she’s brought right in.
6.09: The Better Half
Joan and Bob prepare to go to the beach. They discuss Pete. He makes a leading statement and she tells him about Pete’s mother’s dementia. The doorbell rings, it’s Roger. When he sees he’s not welcome, Roger is stammering, uncomfortable.
Bob offers to excuse himself, but Joan says no, Roger’s just leaving. After he leaves, Bob fishes for information about Joan and Roger being “friends.” She reveals nothing.
At the office on Monday, Bob approaches Pete about a nurse, Manolo Cologne, saying that Manolo “brought my father back to full health.”
He tells Pete that Joan only told him because she’d exhausted her resources, which isn’t remotely true. He has the information all written out for Pete.
6.10: A Tale of Two Cities
When Ginsberg loses it with Cutler, Bob tries to intervene, telling “Michael” that Cutler is his boss. Cutler screams at Bob to stop coming down to Creative.
Later, Bob goes to see Cutler. He defends himself about the argument earlier. Cutler says “I don’t know what you’re talking about,” and Benson follows his lead. Cutler sends Bob to Manischewitz tomorrow afternoon in his (Cutler’s) place, claiming Bob needs to be proven in the field.
The next day, Bob is listening to an inspirational record about sales in his office. He receives a phone call to come help Ginsberg, and runs to Creative. Ginsberg is freaking out.
Ginsberg has taken Cutler’s dressing down to heart. He hates that he’s “The Man.” Bob, calling him Michael (which Ginsberg hates), pep talks him, almost certainly with stuff from the record he was listening to. He says he admires Ginsberg. Bob succeeds in calming Ginsberg, who then asks Bob if he’s “a homo.” Bob doesn’t answer.
The next day, Bob interrupts Ted and Cutler to tell them Manischewitz didn’t go well. They haven’t liked the work for months, they barely listened to the presentation. Ted is angry at Cutler for not going. Bob covers for him, saying it was his own idea. Cutler assigns Bob to Chevy as a reward.
When Pete praises Manolo and tells him Bob was right to recommend him, Manolo says “Mr. Benson is a wonderful salesman.”
Later, when Pete confronts Bob with the information that Manolo and Pete’s mother seem to be having an affair, Pete realizes he never even told Bob he needed a nurse.
Bob tells him to calm down and sit down, which Pete does. Bob brings them both drinks. He suggests that maybe Dorothy is confused about the relationship. Bob implies that Manolo is gay, Pete says if he’s a “degenerate” he’s capable of anything. Bob’s face freezes. Bob insists that Pete drink and tell all. Bob downs his own drink, Sits next to Pete, talks about love. His face is open and it’s clear that it’s a declaration of love for Pete, without naming it. He lets his knee touch Pete’s knee, and he gazes at Pete.
Pete sees the gesture, pulls his leg away, and says “it’s disgusting.” He tells Bob he’ll give Manolo a month’s pay to leave. Bob pulls himself together and says “of course” as if the pass never happened. It’s a total change of tone. His face falls once his back is to Pete.
6.12: Quality of Mercy
Bob is in the Chevy meeting, which makes Pete unhappy. Jim Cutler says he likes Bob and Chevy likes Bob.
After the meeting Pete shakes hands with Bob. Under the guise of publicly shaking hands they have a tense conversation. Bob asks if there’s a problem, Pete calls him “sick” and says he doesn’t want to work with him. Bob denies he professed love and says he doesn’t care about the personalities, just about the account. Bob is quietly threatening.
In his office, Bob is on the phone with Manolo, speaking Spanish, saying that Pete Campbell is a son of a bitch. Bob says he doesn’t care how nice Dorothy is, Pete is messing with his future.
Manolo has told Dorothy to tell Pete that he is upset about the way Pete is treating Bob.
Pete gets a call from Duck Philips. Bob Benson, Duck has learned, is a total fraud. He didn’t go to Beloit or Wharton. He’s from West Virginia. His parents “are brother and sister or something.” At Brown, Brothers, Harriman, he was a manservant to a senior VP for three years. The VP took him to Europe on the Queen Elizabeth. Bob gave three references, of which two were non-working numbers at K&E. The third, at Cunningham, said Bob just disappeared one day “with an electric pencil sharpener and the Christmas card list.”
Bob is in his office, listening to a record, when Pete comes in. Pete confronts Bob, tells him what he knows about him. Bob asks for a day’s head start, but Pete says he will “surrender,” not fire Bob, and not interfere with him, on condition that he (Pete) is off-limits to Bob, and that Bob get Manolo away from Dorothy.
6.13: In Care Of
Pete arrives from Detroit. He doesn’t like the city but he loves the account. Bob Benson is also back from Detroit. He has brought a toy car for Joan to give to Kevin. Roger spots them and is jealous. Joan says Chevy has given Bob a car.
Roger asks Caroline to get Bob Benson, but Bob is already there to see him. Roger tells Bob to stop giving gifts to Joan or playing with her feelings. He sees Bob’s relationship with Joan as a career move; Bob says they’re “buddies.”
On the phone with the authorities, Pete discovers that Manolo had married his mother before she died. He’s enraged. He rushes out to catch a flight to Detroit, and meets Bob in the elevator, on his way to the same flight. He confronts Bob and screams that his friendship with Manny makes him an accessory to murder. Bob swears he knew nothing about it, but Pete isn’t appeased.
In Detroit, Pete and Bob chat with Chevy executives. Pete cuts Bob out of their dinner plans. Bob responds by manipulating Pete into driving a Camaro that’s on display in the Chevy lobby, knowing Pete can’t drive a stick. Pete inadvertently reverses, knocking over a very tall sign. The Chevy guys are disgusted. Bob smiles.
Thanksgiving: Joan answers her door, welcoming Roger. Bob Benson is already there. Roger is upset to see him, but accepts it and plays with Kevin.
Bob is mentioned verbally as being in Detroit in episodes 7.01 (Time Zones) and 7.02 (A Day’s Work), but does not appear on-screen except in episode 7.06.
7.06: The Strategy
Bob arrives from Detroit at the SC&P offices with two execs from Chevy. One of them we know from Season 6. The other is Bill Hartley, newly promoted. Bob is greeted by Joan with a kiss on the cheek. He says he wants to see her Sunday, and she agrees, saying if he wants to see Kevin he’ll also have to see her mother.
That night, Bob is awakened by a phone call. Bill Hartley has been arrested for trying “to fellate an undercover officer”. Bill knows that Bob will be discreet. He’s clocked Bob, but Bob denies he’s gay. Hartley reveals that Chevy is firing SC&P and taking the XP work in-house, as they always intended. The work was an audition. Buick will offer a great job to Bob. Bill’s wife “understands,” he says. Bob is lost in thought.
On Sunday, Bob arrives at Joan’s with gifts for Gail and Kevin, claiming he has nothing for Joan. That night, after Gail and Kevin are asleep, he gives Joan a ring, proposing marriage. She says he doesn’t belong with a woman, but he is offering an arrangement so that he can be the right kind of executive at Buick. She turns him down and shows him out.