Don Draper is a very complex character and I believe the terrible actions he made in his work and personal life stems from the very beginning of his life: his childhood.
THE CREATIVE GENIUS
He is the man responsible for bringing in the cash flow to the business. He is a talented and creative businessman who knows how to identify clients’ needs and pitch the right ideas. In short, Don has proved himself a valuable asset to the firms he has worked for, even earning a CLIO Award for himself. He is a great mentor and friend to Peggy Olson as well, often providing his personal advice to the up and rising girl in Madison Avenue. Interestingly this was possibly the few non-sexual, strictly platonic relationships Don has with a woman.
He possesses strong ethics as seen when he had a dispute with Joan who had volunteer to sleep with a Jaguar executive to land that account in return to being a full partner at the new firm Sterling Cooper Draper Pryce (SCDP). However, there are occasional moments where his professional self gives way. In season 6 Don ruins up a client meeting when he implicitly requests the clients to pull connections to prevent the son of a woman Don was having an affair with from being drafted.
In seasons 5 and 6, his alcohol problems take over him and gradually, we see the distraught and miserable side of Don where his work ethics start to deteriorate. Much to Ted Chaough’s annoyance, Don develops the habit of calling the shot in the office without consulting the partners in the firm. The rivalry between Ted and Don reached its peak when the latter embarrassed the other in a client meeting, nearly resulting an awkward situation where Ted admits his feelings for Peggy in a client meeting (S6E12). As the Chinese idiom goes, one mountain cannot contain two tigers. Ted, Don and Stan desire to escape to sunny California and away from the hectic New York city life when Sunkist demands a guy in the West coast. At the end of the day, Ted is the lucky one who flew west. Unfortunately for Don, his marriage troubles with Megan remain unresolved and his state of mind worsen. Ultimately, Don breaks down in tears and confesses about his impoverished childhood during the Hershey’s Kisses pitch.
“It was the only sweet thing in my life”
Donald Draper in “In Care Of”
P.S. my favourite pitches in the show are mostly by Don and Peggy and they are (strictly not limited to this short list):
- Belle Jolie in S1E6 (because it was here did Don first recognised Peggy’s talents)
- The Nixon Campaign in S1E10
- Heinz Beans, various episodes (I mean who doesn’t love beans?)
- Honda in S4E5
- Hershey’s Kisses in S6E13

Credit: https://www.grubstreet.com/2017/03/heinz-don-draper-mad-men-ad.html
While he is a successful and likable businessman, one of Don’s greatest weakness is the inability to adjust and his need to be in control. When given an open-dated leave of absence from SCDP, what the partners actually want is for Don to seek employment elsewhere. With the exception of Roger Sterling and Pete Campbell, nobody really wants him back and we can see why: the partners felt that Don will not suit the new dynamics. We see from his point-of-view and we see a frightened Don as he struggles to fit the new environment. For instance, Dawn Chambers, his ex-secretary, got promoted to office manager and Don Draper has to report to Lou Avery. In simpler terms, in a fast-moving industry like advertising, Don has lost. When SCDP was absorbed into McCann Erickson, Don could not even sit through a meeting and he did what nobody is expecting: a road trip to Wisconsin.
THE HUSBAND
He is rich, charming and capable. Donald Draper is living the chased-after American dream but things are not as rosy at all in his personal life. Although his relationships with his ex-wives were rather affectionate, Don is guilty of infidelity with countless of women who have crossed paths with him. In the pilot episode, Don’s drawer (at his work desk) is revealed to store many white shirts, hinting to us that he often spends the night outside of home.
He has three children with his first wife Betty but they divorced midway in season three. He then marries his secretary and later a television actress Megan. He cares for his children Sally, Bobby and Gene well and wants to remain as a father figure in their lives. But actions speak louder than words. Donald Draper, like their mother Betty, is not a good father figure for the children.
Pushing his businessman persona aside, Don is a contradictory man in his personal life. A man of high caliber, Don, however, continues to seeks refuge and comfort in women and alcohol. There is no healthy outlet for him to vent his frustrations away. Like every guilty pleasure, this only pushes Don further down the rabbit’s hole. It seems that Don wants to be in control of others’ lives but at the same time, is seemingly unaware of him losing control of his own life.
THE LIAR
Donald Draper is a mysterious and reserved man too. In the entire show, only a few people say 2 – 3, truly know him inside out. Even Betty did not know anything about Don’s past when they first met. Known to only a few, Don’s true identity is revealed to be Richard “Dick” Whitman, a soldier from a poor and dysfunctional family. He assumed the identity of Lieutenant Donald Draper when he was killed in front of him during the Korean War as a means to escape from his background. And this truth is known to only a few, including the wife of the real Donald Draper, Anna Draper. Don Draper has been stuck in this big secret ever since. He is given a chance to renew his life but living in a life created out of a lie has proved too much for him to bear. Apart from Anna who later died of cancer, no one can truly penetrate the man behind countless successful advertising campaigns.
No amount of material wealth and ladies can satisfy Don Draper. What’s more is that Don is unable to commit himself entirely to someone. Alcohol and sex can free him of his huge responsibilities and stress but only temporarily. His childhood experiences and upbringing in a brothel is a double-edged sword; it pushes him to success even to creating a new persona but it also proves that he is not good enough.
But the problem is this: how can he be satisfied when he does not know who he is? The advertising genius is not pleased himself because he is not himself. Simply put, Jon Hamm’s character is acting up because the boy from Pennsylvania is merely roleplaying a character he knows nothing about, like an actor reading the scripts of life. The real Donald Draper has died in Korea and as he later explained in S7E13, he ‘killed’ his commanding officer. Is he still Dick Whitman hiding behind the identity of Donald Draper? Or has he fully assumed the identity of his lieutenant? We cannot confirm this because our character is unsure of it himself.
THE NEW DONALD DRAPER
I am glad for Don when he shared with his children the neighbourhood he grew up in the moment he took a mandatory leave of absence. For a long time we have seen this man rise up the corporate ladder while falling into a bottomless abyss that is his personal world. It really was an emotional moment when we get to witness Don finally starting to come to terms with his reality instead of running away. It is time for Don to take a break from constructing ideas and images for others and start generating ones for himself.
The journey to satisfaction and fulfillment in Don’s life was not smooth. Stephanie left him halfway in the resort and as he confesses his wrongdoings to Peggy over the phone, he had a sudden epiphany and he realises that he has no home to go to. But Don is a smart man. He knows how to get himself together and he is finally at peace with himself in the series finale.
We don’t know for sure if Don assisted Peggy with the 1971 Hilltop advertisement with Coca-cola when Peggy reached out to him. But I believe that the television advertisement could not have escaped Don’s natural talent in painting ideas into consumers’ minds. Don is simply not the guy who would give up easily. It is at a cliff – a place of high-attitude – did Don finds himself and the idea for Coca-cola might have conjured to him when he is meditating. coincidentally, the television advertisement was filmed at a hilltop.

Credits: https://legomenon.com/mad-men-meaning-ending-series-finale.html
I love Mad Men and I love its characters equally. I would give this series a re-watch but unfortunately, nothing can take the magic away from understanding this character again. Thank you Jon Hamm and Matthew Weiner.
P.S. I feel that Don Draper is very much similar to Bojack Horseman.