Mad Men: 10 Greatest Betrayals, Ranked
Mad Men: 10 Greatest Betrayals, Ranked

Intrigue, deceitfulness, and betrayal were all integral parts of Mad Men, and no one could escape either being manipulated or manipulating.

The ten years portrayed in Mad Men (1960-1970) were ones of drastic change. On the show, it’s evidenced by clothing, the decor, and women’s roles in business. During this decade, we also watched Sally, Bobby, and Gene Draper grow up; Sally, in particular, morphed from mischievous little girl who stole 5 dollars from her grandfather’s wallet to a smart-aleck teen who got kicked out of Miss Porter’s finishing school, to a responsible young adult who would eventually replace her mother as the matriarch of the family because of Betty’s cancer diagnosis.

The adults grew and changed as well. New businesses were started; there were marriages and divorces (and affairs); the ad agency won and lost clients as well as employees; babies were born, and people died. One thing that didn’t change was the way these people back-stabbed each other, with Don aka Dick Whitman, being the leading contender.

When Lane Betrayed His Partners

Mad Men: 10 Greatest Betrayals, Ranked
Mad Men: 10 Greatest Betrayals, Ranked

Sterling Cooper Draper Pryce got back on its feet after a dry spell, just in time to gift employees with Christmas bonuses. The partners decided to forgo their shares of the spoils to have some money in the coffers. This did not sit too well with Lane, who was in the hole.

So he wrote himself a check, planning sincerely to pay back SCDP. Before that could happen though, Don found out, fired Lane for embezzling, (no legal action would be taken if he just packed his things and left), explaining that he could no longer be trusted by his partners. The shame of it all was too much for the Brit, who hung himself in his office.

When Don Betrayed Sally

Mad Men: 10 Greatest Betrayals, Ranked
Mad Men: 10 Greatest Betrayals, Ranked

Don wasn’t a good father to Sally, betraying her in several senses. During her birthday party, when Betty sent Don to pick up the cake, he just kept on driving, forcing the blonde hostess to accept a frozen Sara Lee from her new neighbor/single mother nemesis, Helen Bishop. Then there was the time he took Sally and some of her prep school friends to lunch, where he flirted with the teens, lightening the cigarettes they shouldn’t have been smoking.

Before she left him, Sally screamed that both he and her mother were narcissists. How does one forget when his daughter caught Don in bed with the upstairs neighbor, who was also the mother of Sally’s friend/crush?

When Pete Betrayed Trudy

Mad Men: 10 Greatest Betrayals, Ranked
Mad Men: 10 Greatest Betrayals, Ranked

Young, rich (he was a Dykeman on his mother’s side), and with a career on the rise, Pete had New York laid out at his feet. He also had a beautiful, equally high society fianc√©. What more could he want? Well, besides Don’s job, he wanted “the new girl.” When he was introduced to Peggy, he was downright insulting.

That very night though, after his bachelor party, he ended up at her apartment. They slept together again on an office sofa, cementing Pete’s terrible betrayal of the woman he was going to spend his life with.

When Don (& Ted) Betrayed Peggy

Mad Men: 10 Greatest Betrayals, Ranked
Mad Men: 10 Greatest Betrayals, Ranked

“That’s what the money’s for,” he yelled after she complained that he gave her no credit for the Glo-Coat commercial, which garnered him a Clio Award. Peggy was given a career opportunity not many women got, and it seemed Don thought that was enough, so he didn’t give her raises and promotions that he would have given to her male colleagues.

After she left him to go work for Ted Chaough, the two men decided to combine their agencies to attract bigger clients, to which her response was, “Are you kidding me?” She began a personal relationship with Ted, who promised to leave his wife and two little boys for her, then changed his mind.

When Greg Betrayed Joan

Mad Men: 10 Greatest Betrayals, Ranked
Mad Men: 10 Greatest Betrayals, Ranked

Deep down, Joan was sad and lonely, and much more capable than her office manager position allowed. Although her affair with Roger Sterling had its perks, she wanted a husband and family.

Not only did she meet a gorgeous man, but Greg was also a doctor. When he was not chosen for a surgical rotation at his hospital, he enlisted and went to Vietnam to do surgery. Now a mother, Joan was happy when her husband finally returned but discovered he was only on leave as he’d re-upped for another tour because being there (as opposed to with her) made him feel important.

When Don Betrayed Megan And Vice Versa

Mad Men: 10 Greatest Betrayals, Ranked
Mad Men: 10 Greatest Betrayals, Ranked

Megan was the receptionist who became Don’s secretary/babysitter, then his wife/copywriter. He thought they had a good thing until she showed her true colors, still harboring the acting bug, and asking to star in the Butler Shoes commercial. It’s clear he now knew his wife’s priority was her career and not him.

When the new Sterling Cooper & Partners opened an L.A. office, Don promised Megan he’d be its creative director so the two could start over in Cali, where she’d have more movie opportunities. Don gave up that job so Ted could save his marriage (by getting away from Peggy). Megan moved there without him. He also slept with their neighbor Sylvia and a waitress named Diana.

When Roger Betrayed Mona

Mad Men: 10 Greatest Betrayals, Ranked
Mad Men: 10 Greatest Betrayals, Ranked

Let’s start with Joan. These two carried on during the workweek (and office hours) eventually producing a son, the aforementioned Kevin. Then during a long, holiday weekend, Roger stayed late for a casting session involving twins. He and Don romance a set, and Roger ends up having a heart attack. Don has to slap him on the stretcher to remind him to call out his wife’s name, not the twin he was with.

When he began openly having a relationship with Don’s new secretary, Jane, that was the last straw. Mona asked for a divorce, blaming Don, inexplicably, for Roger’s wandering eye.

When Don Betrayed Betty

Mad Men: 10 Greatest Betrayals, Ranked
Mad Men: 10 Greatest Betrayals, Ranked

Midge the Greenwich Village beatnik/artist; Rachel Menken, department store heiress/client; Joy, the free-spirit from the Palm Springs business trip he bailed on; Bobbie Barrett, Utz spokesman Jimmy’s wife and manager; Shelly the stewardess from the Baltimore trip; Suzanne Farrell, Sally’s teacher; Candace the call girl; Allison, his secretary.

And more: Bethany Van Nuys, the socialite; Faye Miller, the research consultant; one-night stands Alice and Doris; Andrea Rhodes, the old girlfriend; and Megan, the younger wife. More than one of these women were let in on Don’s “secret.” Don betrayed his first wife so many times, it becomes almost impossible to keep count.

When Joan Betrayed Don

Mad Men: 10 Greatest Betrayals, Ranked
Mad Men: 10 Greatest Betrayals, Ranked

These two go way back. Even though they don’t socialize outside of work, they have a friendly co-worker relationship and enjoy mutual respect. When Don finds out that Pete and the other partners have offered Joan a piece of Sterling Cooper & Partners if she sleeps with the Jaguar client in order to get the business, he is furious.

He goes to her apartment to beg her not to do it, but unbeknownst to him, she has already returned from her “date.” The next day when Pete gathers the partners to announce they are now the car company’s ad agency of record, Don is visibly disappointed that Joan is in the meeting.

When Don Betrayed Everybody Else

Mad Men: 10 Greatest Betrayals, Ranked
Mad Men: 10 Greatest Betrayals, Ranked

His family, the government, and the widowed Anna Draper. Switching dog tags with the real (deceased) Don Draper probably seemed like a good idea at the time to a young Private Whitman who was going to get discharged but didn’t want to go back to his old life.

Thinking Dick was dead had a profound effect on his younger brother Adam. (The two men eventually reunited, and Don was so mean to him, the dejected sibling killed himself.) Anna is the only one for whom Dick felt any guilt, and he spent his life trying to make things up to her.

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