In 1938, Dole, then known as the Hawaiian Pineapple Company, offered to take the American artist Georgia O’Keeffe on a paid trip to the Pacific island to paint their flagship fruit for an upcoming marketing campaign.

Although O’Keeffe wasn’t a fan of commissions, especially commissions coming from large corporations, the deal arrived at an opportune time. The 51-year-old artist was eager to get away from her husband, photographer and gallery owner Alfred Stieglitz, whose affair with activist Dorothy Norman had contributed to her suffering several nervous breakdowns.

At the same time, she hoped that the Hawaiian landscape—utterly different from the New Mexico environments she frequently depicted in her paintings—would silence critics who had begun to label her increasingly monotonous work as “a kind of mass production.”

While O’Keeffe was blown away by the natural beauty of Honolulu’s pineapple fields, which she described as “all sharp and silvery stretching for miles off to the beautiful irregular mountains,” the first round of paintings she produced for Dole upon returning home the following year included everything but pineapples. Among an array of interesting subjects, she painted lobster-claws, papaya trees, dried lava, and waterfalls. But why?

Georgia O’Keeffe, Hibiscus with Plumeria (1939) on view at the New York Botanical Gardens. Photo: Christina Horsten / picture alliance via Getty Images.

The artist’s distaste of commissions likely contributed to this unusual decision. She was notoriously difficult to work with, not in the least because—in the words of art historian Sharyn R. Udall—her “energies and emotions were intimately intertwined” to the point that “the strain of working to a company’s specifications… created tensions and discord.”

Accounts of O’Keeffe’s stay on Hawaii suggest that Dole’s rigid travel plan made the artist even more disinterested in completing her assignment. The company’s executives, for one, rejected O’Keeffe’s request to sleep close to the pineapple plantations, arguing it would be “improper for a woman to live among the laborers.”

For another, instead of allowing her to paint pineapples outside, in the field, they expected the artist to paint her subject in a studio, removed from nature. To make matters worse still, the pineapples they provided her with were peeled, cut up, and—as O’Keeffe herself put it—“manhandled.” In short, unworthy of being painted.

Sneaking of, O’Keeffe spent two months traveling to and from a sizeable portion of Hawaii’s 137 islands by herself. The highlight of this journey was her stay at a sugar plantation in the town of Hana, on Maui, where she was shown around not by the plantation’s owner, but his 12-year-old daughter, Patricia. In a letter addressed to Stieglitz, she joked about her procrastination, writing, “By the time I leave the islands I am going to know so much more about sugar than I do about pineapples that is funny…”

It goes without saying that Dole wasn’t happy with the lack of pineapples in O’Keeffe’s commission. Insisting she fulfill her end of the bargain, the company actually delivered one straight to her home in New Mexico. If she had disliked the fruits she had seen in the Pacific, this one proved to her liking.

“It’s a beautiful plant,” she later told a reporter from TIME magazine. “It is made up of long green blades and the pineapples grow on top of it. I never knew that.”

True to her style, O’Keeffe painted only a part of her subject, in this case, the sharp leaves that make up the pineapple’s crown. Rendered with reds, greens, and oranges, the end result is just barely recognizable as a pineapple. Still, considering everything its marketing team had been through, the image was good enough for Dole, and promptly featured in advertisements in Vogue, the Saturday Evening Post, and other magazines.

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