Don Draper, 88, maverick ad man, is dead.

Don Draper, an advertising copywriter and creative director whose ideas and campaigns were some of the most thought-provoking and talked about of the decades between the sixties and nineties, died Tuesday at his son’s home in Hudson, New York. He was 88.

The cause was cardiac arrest, said his lone surviving son, Robert Draper. Robert served as his father’s caretaker and companion during the last decade of his life, and his bed and breakfast in the quaint river town provided his father’s last residence.

“One of the world’s most well-known, well-loved, well-hated and misunderstood advertising geniuses,” is how he was described by Peggy Olson-Levitt, former Worldwide Chief Creative Officer of McCann, one of Draper’s many students and protégés. “I’d called him an enigma shrouded in mystery wrapped in a paradigm, but if I did he’d say, ‘What the hell does that mean?’ Let’s just say he was complicated.”

Mr. Draper’s co-workers ranged from past AAF president Roger Sterling (deceased since 1982), to Pete Campbell, chairman emeritus of the Omnicom Group, to Harry Crane, partner now retired of the United Talent Agency. His students ranged from Ms. Olson-Levitt, to Stan Rizzo, art director and creator of the “Hippie, Trippy, Dippy Daddy” syndicated comic strip, to Michael Ginsberg, former copywriter and celebrated film writer and director.

“Don drove me to be better, to think harder, to write better and ultimately – he actually drove me crazy. And when I got crazy, I got famous,” said Ginsberg, speaking from the set of his latest filmed-in-Manhattan movie. “Don also taught me a character’s ‘moral center’ isn’t a solid core but more of an amorphous, gassy blob.”

Much like the man himself, Mr. Draper’s work was memorable, hard to miss, and often polarizing. In the 1960’s, he and a handful of other advertising mavericks ushered in the “Big Idea” era of advertising. Mr. Draper and his agency Sterling Cooper Draper Pryce created iconic campaigns for clients ranging from Kodak, RJ Reynolds, Hilton Hotels, Nabisco Foods, Peter Pan and many others.

In the 1970’s, the agency (re-branded Draper-Campbell), created campaigns for Chrysler that had Ricardo Montalban memorably touting the Cordoba’s “rich, Corinthian leather.” They had the world singing, “There’s a fragrance and it’s here to stay and they call it Charlie.” And they reminded us that die-hard Tarryton smokers, despite the Surgeon General’s increasingly ominous claims, “would rather fight than switch.”

“We made a lot of friends but pissed off a lot of people with our work back then,” Mr. Campbell said. “Frankly, I think Don was happiest when he was pissing people off. It meant people noticed what we were doing.”

Draper-Campbell’s run ended in the early 1980s when it sold its interests to McCann-Erickson who absorbed their clients and gradually retired the name. Mr. Campbell remained with the agency the rest of his career but Mr. Draper quit abruptly. “I refuse to be a name reduced to an initial reduced to a ghost and managed by idiots. So I quit.”  So read Mr. Draper’s short-but-memorable company wide memo, announcing his decision.

Even if he bypassed the traditional “leaving to pursue other interests” memo typically favored by departing ad execs, Mr. Draper did pursue other interests with typical relish and abandon. He briefly joined his friend John DeLorean’s new car company as chief advertising officer before DMC met its infamous and untimely demise. He pursued commercial real estate interests with his fourth wife, Amanda, before their contentious divorce dissolved that business. He even briefly returned to his first career, as a furrier, opening a slew of high-end fur boutiques in major cities just as the fur business reached huge popularity in the late eighties. Yet, despite his success, Draper’s first love remained advertising and it called him back one last time.

“Dad made a fortune in the fur business but it bored him. When he saw the ‘new’ advertising being done in the late eighties and early nineties by shops like Fallon, Chiat/Day and Goodby, he wanted back in,” said Robert Draper. ‘There was a truth and edge to the best stuff they were doing and he wanted to show the world he still had an edge.”

He abruptly sold the fur boutiques and launched Draper. He recruited fresh young talent with a series of provocative print ads placed in the trades. He started lining up client service and working the phones with the legendary Draper charisma and charm. He developed a simple client-acquisition strategy: “Let’s pursue clients who refuse to be boring and who refuse to be ignored.”

It was a strategy that worked. Draper won award after award for brash, abrasive and unforgettable campaigns for clients ranging from Yugo to Seiko, from Budweiser to The Archdiocese of New York, from Playtex to Sony.

“We were hot, everyone wanted to work with us,” said former Draper creative director Sal Romano. “Even clients who probably shouldn’t have worked with us, like Oldsmobile—that was really the end.”

The Oldsmobile client came to Draper after years of perilously falling sales and “consumer irrelevance,” according to former Oldsmobile advertising manager John Rock. “They approached us asking for the equivalent of a ‘Hail Mary Pass,” Romano said. “Don went all in.”

Draper’s approach was indeed brash and different. Operating off the insight that most cars were “sold as thoroughbreds even though most people are using – and treating them – like mules” Draper offered up a very unconventional approach. His TV commercials showed people picking up their new Oldsmobiles and immediately treating them with nonchalance; tossing half-empty cups of coffee on the floor, never washing them, parking where they were easily dinged. Copy touted Oldsmobile as the car “you don’t have to care about from day one, so you can spend more time caring about the things that matter.” The tagline was no longer “It’s not your Father’s Oldsmobile.” It became infamously, “Oldsmobile.  It’s the rental car you buy.” Print ads featured the car with famous-but-unattractive actors, musicians and celebrities with the headline, “Pretty. Ugly.” and copy that touted “pretty is nice but homely works better.”

The can garnered much attention for the brand, almost none of it positive. Oldsmobile sales dipped even more precariously and Draper was quickly fired. “Things went downhill pretty fast after Olds,” Romano said. “Pretty much all the clients starting pulling out. Personally, I still think it was a great campaign, just ahead of its time.” Draper closed its doors for good in 1995. Don’s last unintended laugh; a utility vehicle Draper developed with the campaign was moved to another division when Oldsmobile folded. Thus was born the Pontiac Aztek.

The collapse of Draper was hardly the only tragedy or disappointment of Don’s life. He was married and divorced five times. His first wife, Betty Francis, died of lung cancer.  Their youngest son, Gene perished in a fire in his stepfather Senator Henry Francis’ ancestral 1880’s New Rochelle home. His daughter, socialite Sally Draper, was killed in a car accident, crashing into a group of persons at a party in the Hampton’s while she was driving intoxicated.

Little is known of Draper’s early years according to his son Robert, other than he grew up in meager circumstances on a farm in rural Illinois after his parents died, he served in the Korean Conflict, and he first moved to New York City in 1954.

Still, Draper’s wit and willingness to provoke never left him. When asked to speak to a group of young creative at a conference in 2000, Don followed a famous direct marketing expert, who told the crowd that ‘the big idea’ era of advertising was dead. The future would be all direct selling and personally crafted messages.” After the speaker finished Don took the stage and gave a short but memorable speech. “The best advice I can give you,” Don told the young audience while pointing at the speaker who had preceded him, “is forget everything that guy just told you.” Then he left the stage.

In later years, a young email copywriter tried to explain the nuances of email copywriting to Don. “My job is to try to get people to read my message before automatically dragging it to the little electronic trash can on their screen,” the young writer told Don. Don said, “It doesn’t sound like you’re an ad man. It sounds like you’re a garbage man.”

The last decade of Don’s life in were some ways his most remarkable. Upon the death of his son Robert’s partner, landscape painter Richard Domingo, and in declining health himself, Draper moved to Hudson to live with Robert and help him manage the bed and breakfast.

“It was unlike anything he ever did before, and I was positive he’d hate it. But he didn’t,” Robert said. “In fact, he thrived living a more simple life.” According to Robert, Don grew as a person too. “Dad and I grew a lot closer in those years,” Robert said. “I once asked him, what makes a great creative?  He told me, ‘A great creative never has exactly what he needs, but makes the most of what he has.’ I think that ultimately sort of describes him as a father as well.”

Don’s quieter last years were still not devoid of his trademark twists and surprises. One of his biggest was suddenly and inexplicably legally changing his name to Dick Whitman five years ago. “He never said why,” Robert said. “He just said he was ready to live Dick Whitman’s life from now on and leave Don Draper’s behind.”

Realizing he was in failing health, Don perhaps made one last appearance.  When he died, Robert found a sheet of paper in Don’s old manual typewriter.  It had a headline, “On my tombstone…”

Crossed out –“Knock first.  I’m probably not alone.”

Underlined in bold face – “You should see the other guy.”

An abridged version was originally published on MediaPost on May 5, 2015