All Of Don Draper’s Secretaries (& Who Was The Best)

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Don Draper (Jon Hamm) had ten secretaries throughout Mad Men, but which one was the best assistant for Sterling Cooper’s handsome ad man? Mad Men ran for 7 seasons from 2007-2015 and it was AMC’s prestigious signature series before The Walking Dead. Taking place from 1960 to 1970, Mad Men centered on Draper and the executives of Madison Avenue advertising agency Sterling Cooper (later Sterling Cooper Draper Pryce and Sterling Cooper & Partners).

As the Creative Director (later a partner) of Sterling Cooper’s various incarnations, Don Draper was a powerful, respected, admired, and sometimes feared figure at the ad agency. While infidelity, promiscuity, alcoholism, and rude behavior (as befitting the era) were common at Sterling Cooper’s workplace, Don still notoriously stood out as “a tough desk” due to Mr. Draper’s fluctuating moods and frequent unexplained absences. Further, Don’s secretary was expected to “manage expectations” about Sterling Cooper’s Creative Director, whether it was lying about his whereabouts to the other executives and to Don’s former wife Betty (January Jones) or making sure Draper’s various needs were met, whatever those needs may be.

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Related: Mad Men: D.B. Cooper Is Don Draper Theory Explained

The job of hiring Don’s secretary, or choosing one from the women already working at the office, fell to Joan Holloway-Harris (Christina Hendricks). Still, despite knowing Draper very well, some of Joan’s hires as Don’s secretary ended up in disaster. Twice, Joan herself had to take over Don’s desk while she looked for a suitable replacement. For his part, Don could be a kind boss and there was always an appeal and prestige to working for him despite how difficult he was. But being Don Draper’s secretary was no easy job no matter how talented or competent his secretary was, and there were some spectacular flameouts – as well as some notable successes – throughout Mad Men‘s run. Let’s meet the ten women who worked as Don Draper’s secretary and determine who was the best at one of the hardest jobs at Sterling Cooper.

Peggy Olson

Peggy Mad Men season 1

Peggy Olson (Elisabeth Moss) was a graduate of Miss Deaver’s Secretarial School when she was hired by Sterling Cooper to be Don Draper’s secretary at the start of Mad Men season 1. Peggy openly disliked the expectations of her and the realities of working as a secretary at Sterling Cooper. Luckily, copywriter Freddie Rumsen (Joel Murray) was impressed by Peggy’s creative mind and recommended her to write copy for the Belle Jolie campaign. Soon, Peggy was promoted to junior copywriter and this launched her career in advertising. After Peggy moved on, Joan asked Don if she should search for “another Miss Olson” and Draper replied, “No, I want someone who’ll be happy with this job.”

Lois Sadler

Lois Mad Men

Lois Sadler (Christa Flanagan) was a switchboard operator in Mad Men season 1, but she was placed as Don’s new secretary in season 2. It didn’t take long for Draper to fire Lois for incompetence as she was completely unsuited to be a secretary, and Lois was sent back to the switchboard. In Mad Men season 3, Lois got drunk at the Sterling Cooper office party welcoming the new head of the agency, Guy MacKendrick (Jamie Thomas King) from Putnam, Powell, and Lowe. Lois operated a John Deere tractor and ran over Guy’s foot, maiming him permanently in a horrifically bloody accident. This was the end of Lois’s woeful stint at Sterling Cooper.

Jane Siegel

Jane Mad Men

Jane Siegel (Peyton List) was “the new girl” hired to replace Lois as Don’s secretary in Mad Men season 2. After Peggy and Lois, Don kept his distance from Jane and didn’t bother getting to know her until she proved herself. However, Jane quickly caught the eye of Roger Sterling (John Slattery), who was unhappy in his marriage. Although she was a competent secretary, the imperious Jane was soon fired by Joan for lying about breaking into Bert Cooper’s (Robert Morse) office with Ken Cosgrove (Aaron Staton) and Paul Kinsey (Michael Gladis). Instead of leaving Sterling Cooper, Jane played the victim to Roger, who overrode Joan’s firing her. But after Roger decided to leave his wife Mona (Talia Balsam) for Jane, Don demanded to Roger: “I want her off my desk.”

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Joan Holloway

Joan Mad Men

As Sterling Cooper’s office manager, Joan also had to step in and serve as Don Draper’s secretary twice, after Peggy and then Jane left. Of course, Joan is uber-competent at her job and she was able to manage Don’s every need while still overseeing the other secretaries and female employees at Sterling Cooper, but her being at Draper’s desk in Mad Men seasons 1 and 2 was always temporary until she could find someone suitable for Don.

Allison

Mad Men Allison

Allison (Alexa Alemanni) joined Sterling Cooper as a receptionist in Mad Men season 1 but she became Don Draper’s secretary in season 3. Allison was an excellent secretary, easily Don’s best in the first half of Mad Men’s seven seasons. Don even brought her over to the new firm, Sterling Cooper Draper Pryce, he and the other partners founded. However, Don’s alcoholism got out of control in Mad Men season 4 and he slept with Allison after the SCDP Christmas party. Don then tried to pretend it never happened and gave Allison a $100 Christmas bonus, which she was insulted by. Allison immediately quit but it wouldn’t be the first time Don Draper crossed the line with his secretary.

Ida Blankenship

Ida Blankenship Mad Men

Ida Blankenship (Randee Heller) was Allison’s replacement who was handpicked by Joan because she was someone Don wouldn’t have an affair with. The elderly and cantankerous Ms. Blankenship was Bert Cooper’s secretary and, in her younger days, she was one of Roger Sterling’s conquests whom he called “the queen of perversion”. After Ms. Blankenship had cataract surgery, her overall competence improved until she suddenly died at her desk in Mad Men season 4, episode 9.

Megan Calvet

Megan Mad Men

Like Allison, Megan Calvet (Jessica Paré) was a receptionist who moved up to Don Draper’s desk. And, like Allison, Don crossed the line with Megan, only this time, he married his secretary. Megan was a French-Canadian aspiring actress and Draper proposed to her after bringing her on a trip to California and seeing how much Megan cared for his children. But as a secretary, Megan was careless and she nearly exposed Don’s true identity by accident by filling out an official U.S. government form (with Don’s false info) and having him sign it without reading. After they married, Don promoted Megan to copywriter but she was unhappy at Sterling Cooper Draper Pryce. Megan left to pursue an acting career before moving to Los Angeles while Don stayed in New York (after initially promising to go with her). Don and Megan eventually separated during Mad Men‘s final season.

Related: Mad Men Theory: What Really Happened To Peggy & Pete’s Baby (And Why)

Caroline

Caroline Mad Men

Caroline (Beth Hall) was Roger Sterling’s secretary at Sterling Cooper Draper Pryce who also covered Don’s desk twice in Mad Men seasons 4 and 5. Caroline stepped in for Allison when she was requested to be part of a Pond’s cold cream study by Faye Miller (Cara Buono) and she was Don’s temporary secretary once again after Megan was promoted to copywriter. Caroline was experienced at the job and knew how to manage the men she worked for. Caroline even got Don a plant for his birthday.

Dawn Chambers

Dawn - Mad Men

Dawn Chambers (Teyonah Parris) joined Sterling Cooper Draper Pryce as the only African-American woman on staff. Joan promoted her to replace Megan as Don’s secretary. Adjusting to SCDP was a struggle for Dawn but she was an excellent secretary who remained at Don’s desk after SCDP merged with Cutler, Gleason, & Chaough to become Sterling Cooper & Partners in Mad Men season 6. Dawn even loyally kept working for Don after he’s put on leave, delivering his mail and messages to his home after hours. Dawn was nearly fired by Joan for punching another secretary’s timecard but Chambers eventually replaced Joan as office manager after she became a partner, and Dawn still kept handling Don’s affairs even in her new role.

Meredith

Meredith (Stephanie Drake) was the last of Don’s secretaries who also started out as Sterling Cooper & Partners’ receptionist. Meredith seemed empty-headed and often drew Joan’s ire due to her many screw-ups but became assertive after she became Don’s secretary and made no bones about her desire to be with her boss after his marriage to Megan disintegrated – although Don spurned her advances. Still, Meredith tried to mother Don and he retained her as his secretary after SC&P was bought by McCann Erickson. When Don vanished, Meredith became Roger Sterling’s secretary along with Caroline until he let her go since he didn’t need two secretaries.

Being Don Draper’s secretary was fraught with challenges and complications but Sterling Cooper’s Creative Director did have a few high-quality assistants. After both Allison and Megan, what Don ultimately needed was someone at his desk who had the skills and patience to handle the mercurial Draper without the dangers of having an affair with Don. Mad Men finally got it right with Dawn, who turned out to be a great fit for Draper and who did her job with great skill and loyalty. Surprisingly, Meredith also turned out to be a good secretary despite her obvious yearning for Draper since Don was both not attracted to Meredith and he also seemed to finally learn his lesson to keep his hands off his secretaries as Mad Men ended.

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