Mad Menleft it ambiguous whether Roger Sterling really hired Don Draper.Mad Menchronicled the saga of Don Draper, the handsome and slick ad man who was Creative Director of Sterling Cooper and, later, Sterling Cooper Draper Pryce. One of the fundamental aspects of Don is that he was a man of many secrets. After all, “Don Draper” was a fiction;Don’s true identityis Dick Whitman, and he swapped identities with the late Lieutenant Don Draper during the Korean War.

Just asDon Draper lied to his many mistresses, his ex-wife, Betty, and nearly everyone in his life, it’s quite possible Don also deceived Roger Sterling to get hired at Sterling Cooper.Mad Menseason 4, episode 6, “Waldorf Stories,” featuredflashbacks revealing howDon met Roger.Don was working at Heller’s Luxury Furs in 1953 when Roger came in to buy a present for his mistress, Joan Holloway. Don was instantly excited when he found out Roger was an ad man, and he included his portfolio with the mink that Roger gave to Joan.

Collage of Don Draper, an ad, and him hugging someone in Mad Men

Did Roger Sterling Actually Hire Don Draper?

“You Said, ‘Welcome Aboard’.”

Mad Men’s “Waldorf Stories” is a pivotalepisode that leaves whether Roger Sterlinghired Don Draper an open question. After Roger ignored several calls and messages, Don found Roger at the lobby of Sterling Cooper and lied about why he was there. Don talked Roger into going for a drink even though it was 10am. Later, a drunk Roger left the bar with Don but gave no indication he hired the"fur guy,“But Don then meets Roger at Sterling Cooper again. Don claims Roger hired him and told him,“Welcome aboard.“YetRoger has no recollection of hiring Don. So, did it really happen?

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It’s possible an inebriated Roger did actually say"Welcome aboard"off-screen, and Don took it as confirmation Roger gave him a job.It’s equally possible Don took advantage of Roger, lied to his face, and conned the uncertain Sterling into believing it happened. Roger andMad Mennever indicate what the truth is. However, Sterling has a habit of saying things he doesn’t mean. InMad Menseason 2, Roger told Jane Siegel he’d fix things when Joan fired her asDon Draper’s secretary, but Sterling never did. Maybe Roger knows he didn’t really hire Don, but he saw something in Draper anyway and let the lie become the truth.

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Why It Makes More Sense Don Draper Conned His Way Into Sterling Cooper

It Could Be Another Of Don’s Many Secrets

To be fair to Don Draper, he seemed genuinely confused inMad Men’s “Waldorf Stories” when Roger Sterling had no memory of welcoming him aboard to Sterling Cooper. But asMad Menhas repeatedly shown,Don is a gifted liar and flim flam man. Even this early version of Don, years before he became the aloof and most desired ad man on Madison Avenue, was more than capable of grifting his way into Sterling Cooper once he fired out Roger’s weakness his irresponsibility and alcoholism.

Roger feels he helped create Don Draper and doesn’t get credit for it.

Even if Don conned Roger into getting hired at Sterling Cooper, it’s also entirely possible Draper came to believe he was legitimately hired. InMad Men’s “Waldorf Stories,“Roger told Joan that his real job is"finding guys like [Don],“with a hint of envy and resentment. Whether or not he hired Don legitimately, Roger feels he helpedcreate Don Draperand doesn’t get credit for it. Don and Roger may see ultimately remember how Sterling hired"the fur guy"differently, butMad Menleaves it open for the audience to read into.