Don Draper is the ultimate antihero. The suave, debonaire Creative Director of a Madison Avenue advertising agency had audiences pulling for him throughout the entirety of the show. In AMC’s Mad Men, Don Draper, played by Jon Hamm, straddled the line of what is morally right and wrong. Don is such a dynamic character that you end up empathizing with him through a lot of the horrible things he does.
Some of the things that might be considered “shameful” to the casual viewer are simply part of his personality or business acumen. The truly shameful things he’s done pertain to taking advantage of people and being inconsistent in his behavior.
Had an Affair With His Neighbor’s Wife
Don is very difficult to get along with, so naturally, friends are hard to come by for him. Season six opens with Don and newfound friendship. He and his apartment neighbor Dr. Rosen seem to be buddies.
The two men are both incredibly bright, diligent workers and the mutual respect they share for each other’s work has struck cord between the two. Shockingly, it is revealed that Dr. Rosen’s wife Sylvia, and Don in the midst of a passionate affair. Dr. Rosen never finds out, but not only is he made out to be a fool by Don, but their friendship is a sham.
Used His Secretary
When Don walks through the office, it’s is as if a rockstar is walking up to the stage. Wherever he goes, women stop what they are doing and fix their gazes on him. Those who he paid attention to, felt special, men included. A subtle compliment melts women and makes men proud. So you can imagine the rare air that is felt when Don turns on the charm for his young secretary, Allison. Allison is young, smart, and of course a secret admirer of Don’s.
She always made sure that Don’s every need was taken care of. Returning home late one night, Don realizes that he left his keys at the office. He calls Allison, who runs them right over and helps him inside to the couch. Don, who is three sheets to the wind, makes a pass at her and the two sleep together. In the coming days, Don treats everything business as usual, breaking Allison’s heart. When she can no longer stand being around him any longer, she quits and is never heard of again.
Used The Death of a Partner for Leverage
In season six, Don merges his agency with Cutler, Gleason, and Chaough. The once rivals are now on the same side of the desk and pitching would be clients together. Sadly, Gleason dies of cancer shortly after the merger, which sends Ted Chaough (his closest friend), reeling and into the arms of Don’s protege Peggy Olsen.
Ted’s feelings get the best of him and he promises Peggy a budget for her commercial that the client has not agreed on. Don swoops in, and just when you think he is going to out the office romance in front of the client, he says the idea was Frank Gleason’s dying wish. The client believes him and it earns the agency some a few more bucks.
Cheated on His Pregnant Wife
Don is prone to many indiscretions. He is particularly weak-willed when it comes to women. By the end of season two, Don is living in a hotel, away from his wife Betty and their two children. She told him to leave after she learned about his checkered past and began to suspect he had been having an affair.
Eventually, she reconciles her feelings and tells him to come home. It takes exactly one episode for him to screw up again. In the first episode of season three, while Don is away from his pregnant wife on a business trip, he is once again tempted by the fruit of another. Don casually sleeps with a flight attendant and then returns home to tell Betty he just doesn’t sleep well when he is away from her.
Threw Money in Peggy’s Face
It can be said that Peggy Olsen is the only one who truly understands Don. They have been tied together from the inception of the show. Their road is windy and consists of many ups and downs. She started as his secretary, but she impressed him enough to be promoted to a copywriter. Don has her work on all of his accounts and demands just as much of her as he does himself.
Each time, she answers the bell. One night, he makes her work late with him. She cancels her birthday plans and breaks up with her boyfriend all for Don’s sake. When she is at her wit’s end and asks for a little bit of recognition, he berates her throws the cash he angrily rips from his wallet in her face. All Peggy wanted from Don was some semblance of gratitude, but instead, she got humiliation.
Wasted Megan’s Time
Don is swept off his feet, both by Megan’s beauty and the touch she has with his kids. The two hastily marry, but the honeymoon stage does not last long. In the span of their short marriage, Don disgraces her and wastes her time. He treats her like a dog on a leash and is unresponsive to her attempts to treat him with love.
He lies to her, cheats on her and does not take her desires to pursue her dreams seriously. The most blatant sign of disrespect comes in season five when following an argument Don gets in the car and drives off, leaving Megan stranded alone at a Howard Johnson’s.
Fired Salvatore Romano
Salvatore Ramano was an Art Director and one of the finer employees Don ever had. At the end of season nine, Lee Garner Jr., the heir to Lucky Strike Tobacco and Don’s biggest client, makes advances towards Sal. Sal quickly rebuffs him and hopes to never speak of the incident, as nobody at the office but Don knows Sal is gay.
A scorned Lee Garner Jr. calls for Sal to be fired, citing creative differences. Roger Sterling doesn’t hesitate to fire Sal, as losing Lucky Strike as a client could close their doors. When Sal turns to Don for help, Don decides not to step in, judge Sal and allowed him to be fired.
Scandalized His Daughter
During the midst of his many affairs, Don was always very careful not to get caught. When he was with Sylvia, it began and end without anybody finding out. When Don does a favor for the Rosen family, Sylvia shows her gratitude by inviting Don over one more time for a secret rendezvous while the apartment is empty.
When Sally, Don’s teenage daughter, enters the Rosen’s apartment unannounced, she is scarred for life at the sight of her father and Sylvia in bed together.
Lied to Anna Draper
After a mixup between himself and a dead man during the Korean War, Don steals the identity of a dead man to start a new life. Anna Draper, the wife of the deceased man, seeks out Don in search of answers regarding her husband.
Instead of trying to help the woman who is desperate for closure, Don lies to her and tries to prove he knows nothing. In the end, Don does come clean with Anna and the two begin a beautiful friendship, but in the beginning, he acted shamefully.
Turned Away His Younger Brother
When Don’s picture appears in the paper for an award he wins, his estranged younger brother Adam shows up hoping to rekindle their long lost bond. While Adam is exuberant that he has reconnected with his brother, Don does not share the same sentiment. To Don, Adam is a relic of his past life and a threat to his current life.
Don agrees to meet with Adam but instead of affection he gives him money and instructs him to move on with his life. Adam, alone and lost in the world, ends up hanging himself.
