Leona Helmsley
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Leona Roberts Helmsley (born Lena Mindy Rosenthal; July 4, 1920 – August 20, 2007) was an American businesswoman. After allegations of non-payment were made by contractors hired to improve Helmsley's
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home, she was investigated and convicted of federal income
tax evasion Tax evasion or tax fraud is an illegal attempt to defeat the imposition of taxes by individuals, corporations, trusts, and others. Tax evasion often entails the deliberate misrepresentation of the taxpayer's affairs to the tax authorities to red ...
and other crimes in 1989. Although having initially received a sentence of 4 years, she was required to serve only 19 months in prison and two months under
house arrest House arrest (also called home confinement, or nowadays electronic monitoring) is a legal measure where a person is required to remain at their residence under supervision, typically as an alternative to imprisonment. The person is confined b ...
. During the trial, a former housekeeper testified that she had heard Helmsley say: "We don't pay taxes; only the little people pay taxes." This quote was identified with her for the rest of her life. Helmsley's flamboyant personality and reputation for tyrannical behavior especially towards her employees earned her the
nickname A nickname, in some circumstances also known as a sobriquet, or informally a "moniker", is an informal substitute for the proper name of a person, place, or thing, used to express affection, playfulness, contempt, or a particular character trait ...
Queen of Mean.


Early life

Helmsley was born Lena Mindy Rosenthal in
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, to
Polish-Jewish The history of the Jews in Poland dates back at least 1,000 years. For centuries, Poland was home to the largest and most significant Jews, Jewish community in the world. Poland was a principal center of Jewish culture, because of the long pe ...
immigrants, Ida Popkin, a homemaker, and Morris Rosenthal, a hatmaker. Her family moved to
Brooklyn Brooklyn is a Boroughs of New York City, borough of New York City located at the westernmost end of Long Island in the New York (state), State of New York. Formerly an independent city, the borough is coextensive with Kings County, one of twelv ...
while she was still a girl, and moved six more times before settling in
Manhattan Manhattan ( ) is the most densely populated and geographically smallest of the Boroughs of New York City, five boroughs of New York City. Coextensive with New York County, Manhattan is the County statistics of the United States#Smallest, larg ...
. After dropping out of Abraham Lincoln High School to seek her fortune, she changed her name several times over a short period—from Lee Roberts, Mindy Roberts, and Leni Roberts—before finally going by Leona Mindy RobertsThe Queen of Mean
from
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's Crime Library.
and having her surname legally changed to Roberts. Roberts' first husband was attorney Leo Panzirer, whom she divorced in 1952. Their only son was Jay (1940–1982), who had four children with his wife, Mimi. Jay died of heart failure at age 42. Leona was twice married to and divorced from her second husband, garment industry executive Joseph Lubin. After a brief period at a sewing factory, she joined a New York real estate firm, where she eventually became vice-president. Roberts was a
chain smoker Chain smoking is the practice of smoking several cigarettes in succession, sometimes using the ember of a finishing cigarette to light the next. The term chain smoker often also refers to a person who smokes relatively constantly, though not nec ...
, consuming several packs a day. She would later claim that she appeared in billboard ads for Chesterfield cigarettes, but her claim remains unsubstantiated.


Career as a hotelier

In 1968, while Roberts was working as a
condominium A condominium (or condo for short) is an ownership regime in which a building (or group of buildings) is divided into multiple units that are either each separately owned, or owned in common with exclusive rights of occupation by individual own ...
broker, she met and began her involvement with the then-married real estate entrepreneur Harry Helmsley. Two years later, she joined one of Harry's brokerage firms— Brown Harris Stevens—as a senior vice-president. At that time, she was already a millionaire in her own right. Harry divorced his wife of 33 years and married Roberts on April 8, 1972. The marriage may well have saved her career, as several of her tenants had sued her the year before for forcing them to buy condominiums. They won, and she was forced not only to compensate the tenants but to give them three-year
lease A lease is a contractual arrangement calling for the user (referred to as the ''lessee'') to pay the owner (referred to as the ''lessor'') for the use of an asset. Property, buildings and vehicles are common assets that are leased. Industrial ...
s. Her real estate license was also suspended, so she focused on running Harry's growing hotel empire. Supposedly under her influence, Harry began a program of conversion of apartment buildings into condos. He later concentrated on the hotel industry, building the Helmsley Palace Hotel on
Madison Avenue Madison Avenue is a north-south avenue in the borough of Manhattan in New York City, New York, that carries northbound one-way traffic. It runs from Madison Square (at 23rd Street) to meet the southbound Harlem River Drive at 142nd Stree ...
. Together, the Helmsleys built a New York real estate empire that included 230 Park Avenue, the
Empire State Building The Empire State Building is a 102-story, Art Deco-style supertall skyscraper in the Midtown South neighborhood of Manhattan, New York City, United States. The building was designed by Shreve, Lamb & Harmon and built from 1930 to 1931. Its n ...
, and the Tudor City apartment complex on the East Side, as well as Helmsley-Spear Inc., their management and leasing business. The couple also developed properties that included the Helmsley Palace Hotel, the New York Helmsley Hotel, the Park Lane Hotel, and hotels in Florida and other states. By the beginning of 1989, twenty-three hotels in the chain were directly controlled by Leona Helmsley. Helmsley was featured in an advertising campaign portraying her as a demanding "queen" who wanted nothing but the best for her guests. The slightest mistake was usually grounds for firing, and Helmsley was known to shout insults and obscenities at targeted employees just before they were fired. On March 31, 1982, Helmsley's only child, Jay Panzirer, died of a
heart attack A myocardial infarction (MI), commonly known as a heart attack, occurs when Ischemia, blood flow decreases or stops in one of the coronary arteries of the heart, causing infarction (tissue death) to the heart muscle. The most common symptom ...
resulting from
arrhythmia Arrhythmias, also known as cardiac arrhythmias, are irregularities in the cardiac cycle, heartbeat, including when it is too fast or too slow. Essentially, this is anything but normal sinus rhythm. A resting heart rate that is too fast – ab ...
. Her son's widow, who lived in a property that Helmsley owned, received an eviction notice shortly after his funeral. Helmsley successfully sued her son's estate for money and property that she claimed he had borrowed, and she was ultimately awarded $146,092.


Tax-evasion conviction

Despite the Helmsleys' net worth totalling over $1 billion, they were known for disputing payments to contractors and vendors. In 1983, the Helmsleys bought Dunnellen Hall, a 21-room mansion in Greenwich, Connecticut, to use as a weekend retreat. The property cost $11 million but the Helmsleys wanted to make it even more luxurious. The work included a $1 million dance floor, a silver clock and a mahogany card table. The remodeling bills came to $8 million, which the Helmsleys were loath to pay. A group of contractors sued the Helmsleys for non-payment and the Helmsleys eventually paid off most of the debt owed to the contractors. In 1985, during court proceedings in relation to the lawsuit, the contractors revealed that most of their work was being illegally billed to the Helmsleys' hotels as business expenses. The contractors sent a stack of the falsified invoices to the ''
New York Post The ''New York Post'' (''NY Post'') is an American Conservatism in the United States, conservative daily Tabloid (newspaper format), tabloid newspaper published in New York City. The ''Post'' also operates three online sites: NYPost. ...
'' to prove that the Helmsleys were trying to avoid tax liabilities. The resulting ''Post'' story led to a federal criminal investigation. Jeremiah McCarthy, the Helmsleys' executive engineer, also alleged that Leona repeatedly demanded that he sign invoices to bill personal expenses to Helmsley-Spear and, when McCarthy declined to do so, exploded with tyrannical outbursts, shouting, "You're not my fucking partner! You'll sign what I tell you to sign." In 1988, then- U.S. Attorney
Rudy Giuliani Rudolph William Louis Giuliani ( , ; born May 28, 1944) is an American politician and Disbarment, disbarred lawyer who served as the 107th mayor of New York City from 1994 to 2001. He previously served as the United States Associate Attorney ...
indicted the Helmsleys and two of their associates on several tax-related charges, as well as extortion. The trial was delayed until the summer of 1989 due to numerous motions by the Helmsleys' attorneys, most of them related to Harry's health. He had begun to appear feeble shortly after the beginning of his relationship with Leona years before and had recently suffered a
stroke Stroke is a medical condition in which poor cerebral circulation, blood flow to a part of the brain causes cell death. There are two main types of stroke: brain ischemia, ischemic, due to lack of blood flow, and intracranial hemorrhage, hemor ...
on top of a pre-existing heart condition. Ultimately, he was ruled mentally and physically unfit to stand trial and Leona would face the charges alone. At trial, a former Helmsley-Spear executive, Paul Ruffino, said that he refused to sign phony invoices billing the company for work done on the Connecticut mansion. Ruffino, originally employed to assist Harry through the Hospitality Management Services arm, said that Leona fired him on several occasions for refusing to sign the bills, only for Harry to usually tell him to ignore her and come back to work. Another one of the key witnesses was a former housekeeper at the Helmsley home, Elizabeth Baum, who recounted Leona telling her, "We don't pay taxes. Only the little people pay taxes." Leona denied saying this. By then, however, the trial was already highlighting her abusive and micromanaging behavior towards family members, employees, contractors and even senior executives. Former employees testified at trial "about how they feared her, with one recalling how she casually fired him while she was being fitted for a dress". Most legal observers felt that Helmsley's hostile personality, arrogance, and "naked greed" alienated the jurors. On August 30, Helmsley was convicted of one count of conspiracy to defraud the United States, three counts of
tax evasion Tax evasion or tax fraud is an illegal attempt to defeat the imposition of taxes by individuals, corporations, trusts, and others. Tax evasion often entails the deliberate misrepresentation of the taxpayer's affairs to the tax authorities to red ...
, three counts of filing false personal tax returns,. sixteen counts of assisting in the filing of false corporate and partnership tax returns, and ten counts of
mail fraud Mail fraud and wire fraud are terms used in the United States to describe the use of a physical (e.g., the U.S. Postal Service) or electronic (e.g., a phone, a telegram, a fax, or the Internet) mail system to defraud another, and are U.S. fede ...
. She was, however,
acquitted In common law jurisdictions, an acquittal means that the criminal prosecution has failed to prove that the accused is guilty beyond a reasonable doubt of the charge presented. It certifies that the accused is free from the charge of an o ...
of
extortion Extortion is the practice of obtaining benefit (e.g., money or goods) through coercion. In most jurisdictions it is likely to constitute a criminal offence. Robbery is the simplest and most common form of extortion, although making unfounded ...
—a charge that could have sent her to prison for the rest of her life. Helmsley was instead originally sentenced to four years in prison, which was eventually reduced to 18 months after resentencing.United States of America, appellee, V. Leona M. Helmsley, Joseph V. Licari and Frank J. Turco, defendants,Leona M. Helmsley, defendant-appellant, 941 f.2d 71 (2d cir. 1991) Justia Law. Available at: https://law.justia.com/cases/federal/appellate-courts/F2/941/71/402848/ (Accessed: 25 January 2025). Nonetheless, when it was clear that she was going to prison, Helmsley collapsed outside the courthouse. She was later diagnosed with a heart irregularity and
hypertension Hypertension, also known as high blood pressure, is a Chronic condition, long-term Disease, medical condition in which the blood pressure in the artery, arteries is persistently elevated. High blood pressure usually does not cause symptoms i ...
. Helmsley's new lawyer, retained to appeal the judgment, was
Alan Dershowitz Alan Morton Dershowitz ( ; born September 1, 1938) is an American lawyer and law professor known for his work in U.S. constitutional law, U.S. constitutional and American criminal law, criminal law. From 1964 to 2013, he taught at Harvard Law Sc ...
. Following the appeal, which resulted in a reduced sentence, she was ordered to report to prison on tax day, April 15, 1992. She was released from custody on January 26, 1994, after serving twenty-one months.


After prison

Helmsley's later years were apparently spent in isolation, especially after Harry died in 1997. He left her his entire fortune, including the Helmsley hotels, the Helmsley Palace and the Empire State Building, estimated to be worth well in excess of $5 billion. Her few friends included Patrick Ward and
Kathy Kathy is a feminine given name. It is a pet form of Katherine, Kathleen and their related forms. Kathy may refer to: People In sports * Kathy Bald (Born 1963), Canadian freestyle swimmer * Kathy May (Born 1956), American tennis player * K ...
and Rick Hilton. A 2001 ''
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'' article depicted her as estranged from her grandchildren and with few friends, living alone in a lavish apartment with her dog. Helmsley was forced to give up control of her hotel empire, since most of her hotels had bars, and New York does not allow convicted felons to hold alcohol licenses. She spent her final years at her penthouse atop the Park Lane Hotel. In 2002, Helmsley was sued by Charles Bell, a former employee who alleged that he was discharged solely for being
gay ''Gay'' is a term that primarily refers to a homosexual person or the trait of being homosexual. The term originally meant 'carefree', 'cheerful', or 'bright and showy'. While scant usage referring to male homosexuality dates to the late ...
. A jury agreed and ordered Helmsley to pay Bell $11,200,000 in damages. A judge subsequently reduced this amount to $554,000. Although Helmsley had a reputation as the "Queen of Mean", some considered her generous in her charitable contributions after her prison term. After the
9/11 attacks The September 11 attacks, also known as 9/11, were four coordinated Islamist terrorist suicide attacks by al-Qaeda against the United States in 2001. Nineteen terrorists hijacked four commercial airliners, crashing the first two into ...
, Helmsley donated $5 million to help the families of New York City firefighters and police. Other contributions included $25 million to New York–Presbyterian Hospital for medical research in 2006 through a charitable trust fund. The donations eventually grew to $65 million to establish the Center for Advanced Digestive Care at the hospital in 2009.


Death

Helmsley died of
congestive heart failure Heart failure (HF), also known as congestive heart failure (CHF), is a syndrome caused by an impairment in the heart's ability to fill with and pump blood. Although symptoms vary based on which side of the heart is affected, HF typically pr ...
at the age of 87, on August 20, 2007, at Dunnellen Hall.
Cardiovascular disease Cardiovascular disease (CVD) is any disease involving the heart or blood vessels. CVDs constitute a class of diseases that includes: coronary artery diseases (e.g. angina, heart attack), heart failure, hypertensive heart disease, rheumati ...
ran in her family, having killed her father, son and one of her sisters. After a week at the
Frank E. Campbell Funeral Chapel The Frank E. Campbell Funeral Chapel is a funeral home located on Madison Avenue at 81st Street in Manhattan. Founded in 1898 as Frank E. Campbell Burial and Cremation Company, the company is now owned by Service Corporation International. Fran ...
, she was entombed next to Harry Helmsley in a mausoleum constructed for $1.4 million and set on ¾-acres in
Sleepy Hollow Cemetery Sleepy Hollow Cemetery in Sleepy Hollow, New York, is the cemetery, final resting place of numerous famous figures, including Washington Irving, whose 1820 short story "The Legend of Sleepy Hollow" is set in the adjacent burying ground of the ...
,
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. Among the few distinctive features of the mausoleum are three wall-embedded stained-glass windows, in the style of
Louis Comfort Tiffany Louis Comfort Tiffany (February 18, 1848 – January 17, 1933) was an American artist and designer who worked in the decorative arts and is best known for his work in stained glass. He is associated with the art nouveauLander, David"The Buyable ...
, showing the skyline of Manhattan. Leona Helmsley was known for not liking dirt, and left $3 million for the 1,300-square-foot family mausoleum to be "washed or steam-cleaned at least once a year". Helmsley left the bulk of her estate—estimated at more than $4 billion—to the Leona M. and Harry B. Helmsley Charitable Trust. In addition to providing directly for her own dog in her will, she left separate instructions that the trust, now valued at $5 billion, be used to benefit dogs. The courts have since ruled that the trust is not legally bound to wishes separate from the trust documents. The will left her
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dog, Trouble, a $12 million trust fund. This sum was subsequently reduced to $2 million as excessive to fulfill its purpose. Her choice was branded 3rd in ''
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'' magazine's "101 Dumbest Moments in Business" of 2007. Trouble lived in Florida with Carl Lekic, the general manager of the Helmsley Sandcastle Hotel. Lekic stated that $2 million would pay for the dog's maintenance for more than 10 years—the annual $100,000 for full-time security (several death threats against the dog had been received), $8,000 for grooming and $1,200 for food. Lekic was paid a $60,000 annual guardianship fee. Trouble died at age twelve in December 2010, at which time the remainder of the funds reverted to the Leona M. and Harry B. Helmsley Charitable Trust. Although Helmsley's wishes were to have the dog interred with her in the mausoleum, New York state law prohibits interment of pets in human cemeteries and the dog was subsequently cremated. Helmsley had four grandchildren. Two of them each received $5 million in trust and $5 million in cash, under the condition that they visit their father's grave site once each calendar year. Their signing a registration book would prove that they had visited the grave. Her other two grandchildren, Craig and Meegan Panzirer, received nothing. In a 2008 judgment, Manhattan Surrogate Court Judge Renee Roth ruled that Helmsley was mentally unfit when she executed her will. Roth reduced the $12 million trust fund for the pet Trouble to $2 million. Of the $10 million originally bequeathed to Trouble, $4 million was awarded to the charitable trust, and $6 million was awarded to Craig and Meegan Panzirer, who had been disinherited in the will. The ruling requires the Panzirers to keep silent about their dispute with their grandmother and deliver to the court any documents they have about her. She left $15 million for her brother Alvin Rosenthal. Helmsley also left $100,000 to her chauffeur, Nicholas Celea.


Reputation

Helmsley acquired the moniker "Queen of Mean", reportedly inspired after an advertising campaign promoting her as the "Queen of the Palace" of the Helmsley Palace Hotel. Helmsley became known by this nickname in the mainstream press. Helmsley was known for "tyrannizing her employees".
Alan Dershowitz Alan Morton Dershowitz ( ; born September 1, 1938) is an American lawyer and law professor known for his work in U.S. constitutional law, U.S. constitutional and American criminal law, criminal law. From 1964 to 2013, he taught at Harvard Law Sc ...
, while having breakfast with her at one of the Helmsley hotels, received a cup of tea with a tiny bit of water spilled on the
saucer A saucer is a type of small dishware. While in the Middle Ages a saucer was used for serving condiments and sauces, currently the term is used to denote a small plate or shallow bowl that supports a cup – usually one used to serve coffee t ...
. Helmsley grabbed the cup from the waiter and smashed it on the floor, then told him to beg for his job. In another account of Helmsley's behavior, she had a
barbecue Barbecue or barbeque (often shortened to BBQ worldwide; barbie or barby in Australia and New Zealand) is a term used with significant regional and national variations to describe various cooking methods that employ live fire and smoke to coo ...
pit constructed for her home.Hammer (1990), p. 243. The work was performed by Eugene Brennan, a personal friend of Jeremiah McCarthy, the chief engineer of Helmsley-Spear. When the final bill came to $13,000, she refused to pay, claiming shoddy workmanship. When McCarthy pleaded with her to honor the bill, citing the favor done on his behalf and informing her that Brennan had six children to support, Helmsley replied, "Why didn't he keep his pants on? Then he wouldn't need the money."


In popular culture

The 1990 TV film ''Leona Helmsley: The Queen of Mean'' starred
Suzanne Pleshette Suzanne Pleshette (January 31, 1937 – January 19, 2008) was an American actress. Pleshette was known for her roles in theatre, film, and television. She was nominated for three Emmy Awards and two Golden Globe Awards. For her role as Emily Hart ...
as Helmsley. Pleshette was nominated for the
Primetime Emmy Award for Outstanding Lead Actress in a Limited or Anthology Series or Movie The Primetime Emmy Award for Outstanding Lead Actress in a Limited or Anthology Series or Movie is an award presented annually by the Academy of Television Arts & Sciences (ATAS). It is given in honor of an actress who has delivered an outstand ...
and the
Golden Globe Award for Best Actress – Miniseries or Television Film The Golden Globe Award for Best Actress – Miniseries or Television Film or Best Actress – Miniseries or Motion Picture Made for Television is a Golden Globe Awards, Golden Globe Award presented annually by the Hollywood Foreign Press Associat ...
. In 1989, a biography entitled ''The Queen of Mean: The Unauthorized Biography of Leona Helmsley'' was published by Bantam Books.Pierson, Ransdell (1989
The queen of mean: the unauthorized biography of Leona Helmsley
New York : Bantam Books.


References


Further reading

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External links



{{DEFAULTSORT:Helmsley, Leona 1920 births 2007 deaths 20th-century American businesspeople 20th-century American businesswomen 20th-century American criminals American female criminals Abraham Lincoln High School (Brooklyn) alumni American hoteliers American people convicted of fraud American people convicted of tax crimes American people of Polish-Jewish descent American businesspeople in real estate Criminals from New York (state) Businesspeople from Brooklyn Businesspeople from Greenwich, Connecticut People from Marbletown, New York Burials at Sleepy Hollow Cemetery American billionaires Female billionaires American businesspeople convicted of crimes 20th-century American Jews 21st-century American Jews 21st-century American women