Veteran Ad Woman Recalls What It Was Like to Work for ‘the Queen of Mean,’ Leona Helmsley

"She was a bully. It was such a torment to work with her," said Maas, who actually used to whisper prayers on her way to meetings, hoping to avoid the forked tongue of her client. "Everybody was afraid of her," Maas adds. "Even her own bodyguard, who'd been a New York City police officer, was afraid of her."

The client? Leona Helmsley.

If you're over 40, a longtime New Yorker or both, that name requires no explanation. The imperious wife of real estate developer Harry Helmsley, Leona—who personally ran six of her husband's opulent Manhattan hotels—was probably the most famous female face of 1980s New York. Much of the reason for that fame was her advertising. Helmsley insisted on appearing in all of her ads, a decision that put her arched eyebrows and crafty smile in newspapers, magazines and on TV for nearly a decade.

Ad exec Jane Maas Investigation Discovery

Leona Helmsley died in 2007, but her face is back on-screen this holiday season. For the second year running, Investigation Discovery has dusted off some old episodes of Barbara Walters Presents featuring the movers and shakers of a generation ago, and Leona Helmsley is one of them.

The episode, "The Queen of the Palace," is what Investigation Discovery group president Henry Schleiff calls "the quintessential example of Barbara's efforts in revealing a woman whose understanding and expertise in branding exceeded even her impressive knowledge of real estate—perhaps creating the template, today, for President-elect Donald Trump." (Hold that thought. We'll come back to it.)

The reappearance of the Walters special, which is also available on demand via Idgo, has put Maas back in the public spotlight, too. No doubt, it'll also win her a new generation of sympathizers. While Helmsley indisputably ran some fine hotels (the portfolio numbered 30 at its peak), she also ran them like Stalin.

Notorious for humiliating her employees and firing them for the smallest infractions, Helmsley was by most accounts the boss from hell. New York Mayor Ed Koch once called her the Wicked Witch of the West, and Helmsley's own attorney conceded she was a "tough bitch."

"A spiteful, extravagant, foul-mouthed woman who terrified her underlings," is how The New York Times sized up Helmsley—in her obituary.

As a general rule, the closer you worked with Helmsley, the more you suffered, meaning Maas suffered more than most. She held down what had to be Madison Avenue's most prestigious yet least desired job: the personal advertising rep for Leona.

The post lasted a mere seven months, but, Maas said, "it was a degrading, terrible seven months."

The groundbreaking ads

Jane Maas first met Leona Helmsley at a party given by then New York Gov. Hugh Carey. As a young executive with Wells Rich Greene, Maas had worked on "I Love New York," the tourism campaign conceived amid the panic of the city's social and fiscal collapse that also yielded Milton Glaser's iconic logo. The mercurial Helmsley had just fired her agency, Berber Silverstein & Partners, (she would wind up firing them four times in total) and was looking for a new ad shop. Maas, who'd just struck out on her own with three employees, got the job.

Maas immediately made the difficult but wise decision to continue with the creative template that the preceding agency had established, one that featured Helmsley (ebullient in cascading ball gowns and her 1980s feathered hair) at the center of all of the ads.

"It was a very, very successful campaign and getting a lot of notice," said Maas. The practice of a high-ranking executive making his or her face an integral part of the brand itself was a novel idea in 1980, and no less a publication than Adweek hailed the ads as "a new chapter in U.S. hotel advertising."

"It's hard for a new agency to continue the last one's work," Maas explained. "But I had learned that very often it is absolutely the best thing to do."

It was. At first, the public ate up the idea of the Queen of the Palace (a reference to the New York Palace, the Helmsley flagship property across from St. Patrick's Cathedral), the no-nonsense lady who applied the white-glove test to her hotels and personally guaranteed a fluffy pillow for your head.

"She captured everyone's attention with her iconic ads," recalls John Tanner, general manager of New York-based Chase Design Group. "Her ads delivered the promise of living like royalty, and the idea of a luxury hotel stay became mainstream."

The impossible client

But Maas' problem wasn't the concept; it was Mrs. Helmsley.

Refusing to be photographed inside any of her hotels, Helmsley would only pose before a blank screen in her penthouse on Central Park South. (Later, Maas slipped in the backgrounds for the various Helmsley properties.) Helmsley also refused to be photographed by anyone except Norman Parkinson, photographer of the British royal family, who had to be flown in from London. Helmsley's wardrobe changes, smoldering moods and penchant for rejecting everything translated to endless days. "We started at eight in the morning and worked until it got dark," Maas said. "The whole thing was grueling."

And what did the billionaire Helmsley pay for Maas' dawn-to-dusk dedication? "Ten thousand dollars for the whole shooting match," she said. "It barely paid for the art director."

Indeed, it was Helmsley's parsimoniousness, exacerbated by her toxic personality, that ultimately proved to be her undoing. In 1987, stories of Helmsley purchasing extravagant items, like a $1 million marble dance floor for her Connecticut mansion, and writing them off as business expenses eventually drew the attention of U.S. attorney (and later New York City Mayor) Rudolph W. Giuliani. Hauled into court to face 235 counts of tax evasion, Helmsley faced a parade of former employees who shared horror stories of what it was like to work for her. Among them was the housekeeper who revealed how Helmsley had once said that "only the little people pay taxes."

Convicted in 1989 on 33 counts of income-tax evasion, Helmsley eventually served 18 months in prison. Hailed as "the Queen of the Palace" in the early 1980s, by 1990 Helmsley was known as "the Queen of Mean" (the title of a subsequent TV movie about her) and saw herself lampooned everywhere from Saturday Night Live to the Howard Stern Show.

The cost of fame

When Barbara Walters finally sat down with a bitter and broken Helmsley, she asked the hotelier what  was to blame for her downfall. "I never should have done the ads," Helmsley said.

Yet those ads—funny to look at now—changed the industry.

"They were groundbreaking," noted Hayes Roth of marketing firm HA Roth Consulting. "They leveraged an existing personality and made it relevant to the brand, and did it long enough that you understood the connection. The hotels and a reputation—and she had a reputation—and she just married the two."

Indeed, by introducing the idea that the owner of a famous brand can become a brand herself and blurring the distinctions between them, Helmsley may have inadvertently shown Donald Trump a thing or two. At least, that's what Maas believes.

"I really think he studied her," she said. "They were rivals, and she never brought him up to me. But I suspect that he took a leaf from her book." (Trump Hotels did not respond to Adweek's request for comment.)

Whatever the case, after her inevitable firing by Helmsley, Maas went on to have a long and successful run with Muller Jordan Weiss. Today, she says that having worked for Helmsley did nothing to help her career. Indeed, Maas wound up in court to help recover photographer's fees. But she does thank The Queen of Mean for one thing.

"I grew a thicker skin," Maas said. "Leona made me grow a rhinoceros hide. And I've become a better person because of that."

Helmsley's mug shot, taken by the U.S. Marshals in 1988 Investigation Discovery