The first time we meet Freddy Rumsen, he's drunk and talking about baseball. It's season one's sixth episode, "Babylon," and Freddy's pretty tanked even though it's not even lunchtime. It's 1960. Later that day, Peggy hands him a garbage can full of lipstick-blotted tissues. "Here's your basket of kisses," she says, and Freddy's eyes light up. He gives her her first copywriting assignment. Maybe we shouldn't be too surprised that Freddy's playing a big role so far in season seven — he was playing a big role all along.
"Babylon" is actually an awful lot like last night's episode "The Monolith": Roger's daughter Margaret swings by his office, just long enough to be petulant and insulting; Paul and Pete talk about Israeli communes and kibbutzes; and Don starts reading Exodus. Nine years later, and not that much has changed. Roger's just as frustrated with his inability to communicate with his daughter, no one's opinions of communes has improved, and now Don's reading another of modern Judaism's most important books, Portnoy's Complaint. At the end of "Babylon," upon getting her first writing assignment, Peggy hopefully asks Joan, "Do I get a raise?" In "Monolith," she doesn't even have to ask for it. The raise lands right on her desk. And oh yeah, Freddy's there, and he's talking about baseball, only this time it's Don who's drunk.
We typically think of Don as Peggy's mentor, but Freddy's the one who spots her talent initially, the one who encourages Don to use her writing, and the one who congratulates her when the pitch is successful. "Home run, ballerina," he says, beaming. When she complains that they'd changed her exact tagline, Freddy laughs. "You may be a writer, honey," he tells her. "You're arrogant." Freddy's also the one who suggests Peggy work on what she eventually renames "the Rejuvenator," giving her her second writing assignment.
Not that Freddy's a complete gem of a human at all moments: He's a guy who plays Mozart on his fly (oh, the days of crazy-long inseams), who doesn't invite Peggy to client dinners that happen after hours, and there's that time he pees himself at the office. That drunken mistake, though, means Peggy's the one who gets to present to Samsonite in "Six Month Leave," just as Freddy is sent packing. In "The Mountain King," season two's finale, Peggy asks for — and gets — his old office.
We don't see Freddy again until season four's "Christmas Comes But Once a Year," at which point he's sober. He brings SCDP Ponds, and Roger rehires him on the spot — except Freddy immediately segues back into ultrapatronizing mode around Peggy, who's not having it anymore. She snaps at him, calling him "old-fashioned," which Freddy takes as a huge insult. They make up, though, and Freddy advises Peggy on her love life: Don't have sex with a guy if you want him to respect you, but don't just lead him on, either.
Freddy appears sporadically in the rest of season four, and then vanishes again until season five's "The Other Woman" — more memorable for Joan and the Jaguar guy than for an intense lunch between Peggy and Freddy. But it's an episode that again finds Freddy in the encouraging mentor role to Peggy — again calling her "ballerina," and this time telling her that she doesn't have to put up with Don's crap if she doesn't want to. It's Freddy who recommends her to Ted Chaough, and Freddy who pushes her to ask for $18,000 a year. (Ted offers $19,000. Peggy and her raises: There's always a catch.)
And that's just about all we see of Freddy until this season's premiere, as he recite's Don's captivating pitch to Peggy. He's still Freddy, scrounging for free coffee and putting his own, slightly less good, spin on things — and most important, he's the Don Peggy needs, not the Don Peggy has. Don is often there for Peggy, but he is not always for her, and he wants what's best for her only when that's what's best for him too. Peggy and Don love each other, and their bond is profound, but Don has been cruel to his protégée, cruel on purpose. In "The Monolith," Don could be helpful or at least a team player, but instead he's resentful, distant, wasted. "Is he in?" characters ask throughout the episode. Physically, yes; mentally and substantively, absolutely not. The last time we saw Don this self-destructive and annihilated at work was in "The Suitcase," when it was Peggy who was watching him barf and letting him sleep it off on the couch. But Don can't just call Peggy this time, so he calls Freddy instead. Over the rest of the show, Freddy's been Don when Peggy needs another Don, but in "Monolith," he's Peggy when Don needs another Peggy.
This season and last season have been bending time; for a show that's of course very literally moving forward (so much emphasis on dates this season!), the same themes and touchstones are bubbling up again and again. It's Valentine's Day — again. It's "My Old Kentucky Home" — again. Everything is happening again and again. The reappearance of Freddy is part of that, and his position indicates Peggy and Don's respective positions in the world. "There's always a hierarchy," Roger tells some random crapbag hippie in "Monolith." He's right, at least for Mad Men if not for the actual meatspace Earth, but Freddy's not part of the SC&P hierarchy anymore — so when we see the show's world through his eyes, we can see those rankings clearly. As Peggy would say, it's quite a view.