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On March 31 1982 Leona's only child Jay Panzirer died of a heart attack resulting from arrhythmia. Helmsley Charitable Trust. A 2001 Chicago Sun-Times article depicted her as estranged from her grandchildren and with few friends living alone in a lavish apartment with her dog.
Following allegations by unpaid contractors that work done on her home had been charged to her company Leona Helmsley was investigated and convicted of federal income tax evasion and other crimes in 1989. Although having initially received a sentence of 16 years Helmsley was required to serve only 19 months in prison and two months under house arrest.