03/12/2026
The man who inspired Don Draper didn’t just build brands. He built a world.
In the 1960s, Rosser Reeves didn't follow the "rectangular" rules of advertising. He lived larger, bolder, and with more narrative flair than most modern agencies could dream of.
We used to visit him at his home in Jamaica—Pimento Hill—a pimento-pink villa perched high above Montego Bay.
Here peacocks roamed the grounds.
Desmond the butler made us rum and Cokes at 11 a.m. (naturally our parents had no idea) while we watched chameleons climb the marble pillars of the veranda.
Mrs. Davis, the cook, served the most delicious avocado ice cream for our poolside lunches.
The pool itself was a work of art.
In the 1960s most pools were rectangular boxes. Rosser declined to conform. He took a hose and traced the outline himself—a wiggling, Salvador Dalí–shaped pool that slipped half in and half out of the pool house.
Pimento Hill was grand.
So grand that Queen Elizabeth once stayed in the master bedroom where golden satin draped the half-canopied bed.
Dinner was a formal affair.
Cocktails started the evening.
Then we moved to the moon garden.
Classic French cuisine was served in the night air perfumed by night-blooming jasmine.
Waiting, it seemed, for Noël Coward to appear from the shadows. Ian Fleming, a neighbor at one time, was not immune to Pimento Hill's charms; he too guested back in the day.
Rosser never treated us as children. To him we were simply miniature adults.
Boisterous and competitive he played backgammon and chess with my brother. Me he challenged intellectually.
The peacocks are long gone. But the allure remains. The image of Pimento Hill still glows like Rosser’s ruby.
I can still hear Rosser and his wife BJ—Betty Joy—his Southern accent smooth as good bourbon.
The lesson for today's brands:
Rosser Reeves knew that luxury isn't a price point; it's a point of view.
In a world of "pre-mixed cocktails and microwave ovens," we’ve lost the art of the distinctive outline.
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