Leona Helmsley: Death and Taxes

The death of billionaire hotelier and real estate maven, Leona Helmsley, today, at the age of 87, serves as testament to the truths of two adages; first, that "the only certainties in life are death and taxes" (Benjamin Franklin), and second, that "only the good die young" (Billy Joel's rock-and-roll twist of Oliver Herford's lesser-known quotation "only the young die good."

The reported cause of death was heart failure, which no doubt comes as a surprise to those, including former employees, certain that she somehow lived her life without that particular organ.

The former model (huh?) and real-estate agent became Mrs. Helmsley in 1972 after convincing Harry Helmsley to divorce his wife. She quickly settled in as his full business partner, and together they built a hotel chain and real estate empire, which at its height included ownership of the Empire State and Flatiron Buildings. She once said that Harry loved having her as a business partner because "the board meeting was over as soon as they got out of bed in the morning." Go ahead and let that visual sink in.

Leona eventually became the face of the brand and centerpiece of a 1980's ad campaign touting the Helmsley Hotels as personally overseen by "the Queen" -- Leona herself. The campaign spotlighted Leona's insistence on having the "very best," indirectly referencing her indifference to and intolerance with the working class who were, to her way of thinking, there to serve her purposes. The campaign resonated with the new wave of high-spending, cold-hearted elitists spawned during the "Reagan years" -- an era for which Leona has attained iconic status. It seems somehow fitting that as she aged, she came to resemble Reagan himself, in very bad drag.

Dubbed the "Queen of Mean" [also the title of the 1990 made-for-TV biopic, which brilliantly cast Suzanne Pleshette in the main role], Helmsley was notorious for her ill treatment of employees, a wickedly short fuse, and insurmountable arrogance. In 1988, the Helmsleys were targeted by then-NYS Attorney General, Rudolph Guiliani, in a tax evasion scheme and were prosecuted. Mrs. Helmsley took it on the chin for her husband, who was declared mentally incompetent for trial, ultimately serving 18 months in a minimum-security prison. The highlight of the trial and the source of the quote most often associated with Leona came in the form of testimony from a former employee of the Helmsleys, a hotel maid, who testified that Leona once bragged that she and her husband "don't pay taxes. Only the little people pay taxes." Charming lady, no?

Harry Helmsley died in 1997 and Leona slithered out of the spotlight saying "[m]y fairy tale is over." She was, however, mistaken. A new "fairy" tale with grimmer consequences brought her back into court in 2003. She was sued by the former manager of the Helmsley Park Lane Hotel, Charles Ball, who claimed he was terminated because he was gay. A jury awarded Ball $1.2 million in compensatory damages and $10 million in punitive damages; the award was subsequently reduced to approximately $550,000. Testimony was clear that she created a hostile environment for Ball and was not a friend of the gays, but the underlying story is a bit more sordid than is often reported. Apparently, Helmsley was incensed that Ball had rented out so many of the rooms to attendees for New York's celebrated night of leather, The Black Party. What I would have given to have been a lady-in-waiting within earshot of Leona Helmsley when she was informed that the lobby of the Park Lane was littered with leather-clad and unclad circuit queens. The world hadn't seen a square-off between two queens this evenly matched since Elizabeth I and Mary Queens of Scots.

Some of those reporting on her life have made special efforts to highlight Leona's philanthropic and charitable deeds in some sort of twisted balancing act to offset the "mean, greedy, bitch" side most people know. For instance, CNN has reported that in her lifetime she likely donated approximately $50 million to hospitals, black churches in the South, and victims of September 11th and Katrina. My response: Yeah, and your point? Frankly, the amount is peanuts in comparison to her worth (estimated by Forbes at $2.5 billion in 2007). My assumption is that the donations were motivated more by tax consequences than any real concern for its beneficiaries.

Mrs. Helmsley will rot alongside her darling Harry, holding what is, I suppose, an eternal board meeting, inside a marble mausoleum worth $1.4 million at Sleepy Hollow Cemetery (ironically the same cemetery where Brooke Astor was recently buried). The mausoleum reportedly has a magnificent view, huge columns, and a breathtaking stained-glass window representation of the New York skyline, including the jewel of their earthly empire, The Empire State Building.

I hope to hell someone remembered to put a mint on her pillow before she arrived at the mausoleum or there's going to be hell to pay.