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 Connecticut home, she was investigated and convicted of federal income tax evasion and other crimes in 1989.

[16] In 1968, while Roberts was working as a condominium broker, she met and began her involvement with the then-married real estate entrepreneur Harry Helmsley.

[20]: 208  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.

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 to prove that the Helmsleys were trying to avoid tax liabilities.

[13] 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 on top of a pre-existing heart condition.

[13] 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.

[13] 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.

By then, however, the trial was already highlighting her abusive and micromanaging behavior towards family members, employees, contractors and even senior executives.

[23] Most legal observers felt that Helmsley's hostile personality, arrogance, and "naked greed" alienated the jurors.

[41] After a week at the Frank E. Campbell Funeral Chapel, she was entombed next to Harry Helmsley in a mausoleum constructed for $1.4 million[42] and set on ¾-acres in Sleepy Hollow Cemetery, Westchester County, New York.

Among the few distinctive features of the mausoleum are three wall-embedded stained-glass windows, in the style of Louis Comfort Tiffany, 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".

[48][49] Trouble lived in Florida with Carl Lekic, the general manager of the Helmsley Sandcastle Hotel, with several death threats having been received.

[50][51] Lekic, Trouble's caretaker, stated that $2 million would pay for the dog's maintenance for more than 10 years—the annual $100,000 for full-time security, $8,000 for grooming and $1,200 for food.

[52] 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.

[16] In a 2008 judgment, Manhattan Surrogate Court Judge Renee Roth ruled that Helmsley was mentally unfit when she executed her will.

[62] Alan Dershowitz, 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.

[64] The work was performed by Eugene Brennan, a personal friend of Jeremiah McCarthy, the chief engineer of Helmsley-Spear.

[64] 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?