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Probate & Property

Jan/Feb 2023

Leona Helmsley: The Queen of Probate & Property? Practical Drafting Tips from Her Majesty’s Wills

William A Drennan


  • On the probate side, Leona Helmsley merits the title Queen of Probate & Property because her will presents and addresses an astounding array of issues.
  • Decedents have the right [by will] to determine the manner and location of the disposition of their remains.
  • Incentive clauses can be enforced if they are not too vague and do not violate public policy.
Leona Helmsley: The Queen of Probate & Property? Practical Drafting Tips from Her Majesty’s Wills
BrianAJackson via Getty Images

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Sensational sobriquets include the King of Swing, the Queen of Soul, the Sultan of Swat, Satchmo, the Say Hey Kid, the Manassas Mauler, and the Man in Black. A worthy addition is that unflattering moniker bestowed upon Leona Helmsley, a/k/a the Queen of Mean. This article proposes a new title for the late Leona—The Queen of Probate & Property. (The common or given names for those highlighting the start of this article, along with many more amazing appellations, are at the end of this article in The 100 Nickname Quiz! Take the quiz and see if you can identify all 100.)

Leona Helmsley established her place in the pantheon of wildly wealthy real property titans over decades, moving from high school dropout, to successful agent, to owning an amazing array of prized properties, including the Empire State Building. Along the way, she married real estate mogul Harry Helmsley in 1972, was convicted of federal tax fraud and spent 18 months in prison before being released on January 26, 1994, and inherited her husband Harry’s fortune upon his death in 1997 under a will he signed the day before Leona was released from prison. After accumulating an estate conservatively estimated at more than $5 billion, she passed away on August 7, 2007. But this article leaves the real property tale for others. See, e.g., Ransdell Pierson, The Queen of Mean: The Unauthorized Biography of Leona Helmsley (1989); Richard Hammer, Helmsleys: The Rise and Fall of Harry and Leona Helmsley (1990).

Instead, this article focuses on the probate side. Leona left a will addressing a cornucopia of issues with practical implications for even not-so-wealthy souls. With the 15th anniversary of Leona’s departing, we can reflect upon a few of her likely estate planning desires, review the related legal techniques used, assess the successes and failures of that planning, and distill some practical implications for today.

This article surveys six probate issues or opportunities, specifically: (i) using a will as the client’s primary dispositive vehicle; (ii) directing that the deceased be buried with valuable property; (iii) directing burial next to a pet; (iv) including long-term burial wishes in a will; (v) bequeathing money for the benefit of a pet or for the maintenance of a mausoleum; and (vi) tying behavior-incentive conditions to a bequest in trust.

Topic #1: Will as Primary Dispositive Document

Leona put out the family laundry, and her misanthropy, for the world to see. A copy of her will is available to all. Last Will and Testament of Leona Helmsley, Living Trust Network, She left $12 million for the benefit of her nine-year-old, four-and-a-half-pound dog, which was more than she left outright to any human being.

Despite the typical reluctance to speak ill of the dead, the public disclosure of her will inspired venom. See, e.g., Jeffrey Toobin, Rich Bitch: The Legal Battle over Trust Funds for Pets, New Yorker, Sept. 22, 2008, at 38. One philosophy professor compared her $12 million doggie transfer to “setting money on fire in front of a group of poor people.” Id. at 48 (quoting Professor Jeff McMahan of Rutgers University).

For some clients, this could be a cautionary tale. In the interest of minimizing public scrutiny, clients can use a simple pour-over will and then a trust containing any unusual terms. The standard pour-over will would be a public document, but the trust with the juicy bits would be available to only the trustees, the beneficiaries, and their advisors. See Susan N. Gary, Transfer-on-Death Deeds: The Nonprobate Revolution Continues, 41 Real Prop., Prob. & Tr. J. 529, 537 (2006) (“[Unlike a will or deed] a revocable trust is not a public document . . . so the owner’s plan of distribution will not be public.”).

Topic #2: Burying Property at Death and Keeping It Buried

Leona’s will directs that she be “interred wearing [her] golden wedding band (which is never to be removed from [her] finger).” One generally can destroy his own property during lifetime, but a direction to destroy property at death may be capricious or violate public policy. One cannot validly bequeath $1,000 to a trustee with the direction to throw the $1,000 “into the sea,” and a trustee who followed such a direction would be liable to the estate for the loss. Restatement of Trusts § 124, cmt. g, Illus. #5. A Pennsylvania court declared invalid a decedent’s direction in her will that she be buried with her “diamonds and other jewelry.” Meksras Estate, 63 Pa. D.&C.2d 371 (Penn. Ct. Common Pleas 1974). The court reasoned that because the will was a public document, obeying the decedent’s direction would encourage grave robbing and thereby violate public policy.

On the other hand, there are many reports of decedents being buried in their cars or with their prized possessions. See Abigail J. Sykas, Waste Not, Want Not: Can the Public Policy Doctrine Prohibit the Destruction of Property by Testamentary Disposition, 25 Vt. L. Rev. 911, 926 (2001). When such a direction, which effectively destroys the property for the living, would be capricious or contrary to public policy is not clear. Id. (referring to the “abstract, amorphous public policy rationale”). A tome voted the creepiest book commonly found in U.S. law libraries indicates that a request to be buried wearing a wedding ring is common. Percival Jackson, The Law of Cadavers 127, 183 (2d ed. 1950).

There are at least two takeaways regarding Leona’s approach. First, in light of concerns about grave robbing, it may be advisable to delete words like “golden” or other modifiers indicating significant value from the description. Second, Leona’s direction that the band should “never be removed from [her] finger” is insightful, as relatives reportedly have reopened graves to recover jewelry. See Kate Meyers Emery, More Famous Dead, Bones Don’t Lie (Dec. 20, 2012), (discussing the reopening of Sammy Davis Jr.’s grave to grab $70,000 worth of jewelry). Although with decomposition the wedding band may fall from Leona’s finger eventually, she likely received some comfort from this will provision.

Topic #3: Burial Alongside a Pet

The media often reported that Leona wanted to be buried with her dog, but actually Leona’s will directed that the dog’s “remains shall be buried next to [Leona’s] remains.” It could have been crowded around Leona, as her will also directed that she be buried “next to” her predeceased husband, as well as “next to” her predeceased son. Leona and her planners were criticized for including this doggie provision because at the time an animal burial with a human was not authorized under either New York law or the rules of her chosen cemetery. Toobin, supra.

Nevertheless, in hindsight, if consistent with the testator’s wishes, it may be wise to include such a provision. State laws are changing. In 2016, New York changed its law to provide that the cremated remains of a domestic animal could be buried with a human being. Many states are still silent on the issue, some states are on the road to change, and some states allow “whole-family” cemeteries with “full-body burial of a pet’s remains in the family burial plot.” See Elder Law 101: Can You Be Buried with Your Pet? (Mar. 4, 2020),; Sara Redding Ochon, Can Pet Ashes Be Buried with Humans? USA State by State Laws, hppts:// (offering a 50-state click-on guide to burying pet ashes with a human).

In this evolving era, what was prohibited today may be authorized tomorrow. As the testator may not die for some time, it may be advisable to include these clauses in a will and also to spell out the client’s “second choice” if legal or cemetery restrictions interfere with the most-favored plan. For example, if either law or cemetery restrictions prohibit human burial with a particular type of pet, would the testator want the animal cremated and the ashes sprinkled on the decedent’s grave (or deposited in an urn that could be buried at the foot of the testator’s plot)? Speaking back in 2013, one industry insider remarked that undertakers “will tell you ‘not a day goes by when I don’t put an urn of an animal into the casket of a human being secretly for a family.’” Elder Law 101, supra.

Her dog died about four years after Leona. Because the dog could not be buried next to Leona, the dog was cremated and the ashes placed in an urn that was “privately retained.” Cara Buckley, Cosseted Life and Secret End of a Millionaire Maltese, N.Y. Times, June 9, 2011. When asked if the dog’s urn had been, or would be, added to Leona’s mausoleum, a member of the cemetery’s board stated, “In all honesty . . . we don’t know.” Id.

Topic #4: Including Long-Term Burial Instructions in a Will

Deeply rooted tensions dominate the law regarding who controls the disposition of human remains. The refusal to find that the decedent has a traditional property right in his corpse suggests that the right of sepulcher rests with the living—usually first a spouse, and if none, the next of kin. Consistent with this view, most states allow an individual to designate an agent to make the decisions under a power of attorney or other document. See, e.g., Kimberly E. Naguit, Letting the Dead Bury the Dead: Missouri’s Right of Sepulcher Addresses the Modern Decedent’s Wishes, 75 Mo. L. Rev. 249 (2010). In reliance on a state statute, the Iowa Supreme Court famously refused to follow a decedent’s clear direction in her will and a signed letter that she be buried in Montana, and instead found that her husband had the right to bury her in Iowa. In re Estate of Whalen, 827 N.W.2d 184 (Iowa 2013).

On the other hand, Roman law and long-standing common law principles respect “that decedents have the right [by will] to determine the manner and location of the disposition of their remains.” Tanya D. Marsh, You Can’t Always Get What You Want: Inconsistent State Statutes Frustrate Decedent Control over Funeral Planning, 55 Real Prop., Tr. & Est. L.J. 147, 150 (2020) (providing a thorough analysis of the history, policy, case law, and legislation for this issue, and including “a comprehensive appendix listing and summarizing each states’ . . . laws as an aid to practitioners”).

Leona’s will not only directed that she be buried next to her predeceased husband and her son at the Woodlawn Cemetery, but also it addressed a possibility far in the distant future. Her will directed that if her husband and son should be relocated, then she also should be relocated and reinterred next to them. She also directed that her brother and his wife be permitted to be buried in the Helmsley mausoleum, “but no other person.” Whether this latter desire would be achieved likely will depend on the applicable deed, agreement, and affidavit regarding the mausoleum and its use. See generally Anne K. Hansen, Who Is in My Grave? A Comparison of State and Local Laws in Illinois and Utah That Guide Resolution of Grave Plot Ownership Claims, 45 S. Ill. U. L.J. 139 (2020).

A will may be strong evidence of the decedent’s intentions regarding the treatment of the body. “For centuries the last expression of bodily autonomy has been received with solemnity and honored by our laws to the fullest practical extent when declared with the formality of the last will and testament.” In re Estate of Whalen, 827 N.W.2d at 195 (Cady, C.J., dissenting). Anticipating the future may be especially relevant when there are doubts about the intended duration of the burial. In some cultures and geographic areas, burial frequently is only for a term of years based on an estimate of the time expected for the body to decompose to a certain extent.

Topic #5: Bequests to Pet Trusts or Burial Maintenance Funds

Leona’s estate may be best known for its influence on estate planning for pets. Her will left $12 million in trust for the benefit of her nine-year-old, four-and-a-half-pound Maltese named Trouble. Honorary trust statutes typically provide that only a reasonable amount may be held in a pet trust and that any excess must pass to the designated subsequent taker or the residuary beneficiary. In response to a request from Leona’s fiduciaries, a New York judge ruled that only $2 million was reasonable for her dog and that the other $10 million was excessive. Nevertheless, a leading pet trust expert astutely observed, “It’s not the reduction that is important; it’s that the judge said two million was appropriate. It’s a landmark case.” Toobin, supra, at 43 (quoting attorney Rachel Hirshfeld). That expert also said, “One of the greatest moments in my life was when the judge awarded $2 million [for the Helmsley dog].” Id.

Although it did not get the media barking like the transfer to the dog trust, Leona’s will also created a $3 million mausoleum fund to maintain, in “excellent condition,” the “final resting places” for herself, her husband, her son, and her mother, father, sister, and brother-in-law. The will also stated that all these final resting places would be inspected at least quarterly and “acid washed or steam cleaned at least once a year.” In addition, the fund may maintain subsequent final resting places if any of them are relocated. Apparently, there has been no challenge to the amount of the Helmsley mausoleum fund, perhaps because there is New York precedent for spending amazing amounts on burial and maintenance. See, e.g., In re Baeuchle’s Will, 82 N.Y.S.2d 371 (N.Y. 1947) (rejecting an argument that spending approximately $150,000 for the decedent’s burial and mausoleum maintenance fund in 1946 was unreasonable when the decedent’s entire estate was $175,000; in today’s dollars the amount spent on burial and maintenance in that case was approximately $2.15 million).

For both honorary trusts, Leona and her planners presumably anticipated the amounts would be challenged and smartly designated a subsequent taker for any amounts determined excessive. With honorary trusts, a common concern is enforcement because, by definition, there will be no surviving human beneficiary with standing to sue to police compliance. Leona, however, appointed five trustees for the mausoleum maintenance trust, so presumably there will be one or more individuals who will monitor compliance. In addition, Leona used her will to help justify the amounts contributed to the mausoleum trust. The will stated the mausoleums are to be inspected at least quarterly, maintained in “excellent condition,” and acid-washed or steam-cleaned at least annually.

In contrast, her will failed to list anticipated expenses that could justify the contribution to the pet trust. It may be advisable for a testator to explain why he is contributing to a pet trust by listing and explaining the expected expenses, such as veterinarian fees, special food, the expenses of a companion animal, and perhaps, most important, a fund for extraordinary drugs and medical care because the testator would prefer that the pet undergo surgery or other complicated procedures rather than being put to sleep. Some owners spend incredible amounts on drugs, surgery, dental care, and various medical treatments for their pets.

Topic #6: Behavior Incentive Conditions

A decedent may desire to exert dead-hand control over the future behavior of the living. Some testators provide incentives for children or grandchildren to end a drug habit and enter a rehab program, end an alcohol addiction, go to college or obtain an advanced degree, wed a member of a particular religious faith, or cease or pursue other activities. See Ellen Evans Whiting, Controlling Behavior by Controlling the Inheritance: Considerations in Drafting Incentive Provisions, 15 Prob. & Prop., Sept/Oct. 2001, at 6. Generally, these incentive clauses can be enforced if they are not too vague and do not violate public policy. Id.

For each of her favorite grandchildren, David and Walter, Leona left $5 million to a charitable remainder trust paying a five percent annual unitrust amount, which would be approximately $250,000 per year (initially) to David and Walter. Leona’s will provided that a grandchild would continue to receive the annual payouts only if the grandchild visited the grave of his father (Leona’s son) “at least once each calendar year, preferably on the anniversary of [his] death (March 31, 1982).”

The will directs the five trustees of the charitable remainder trust to place a visitor book in the mausoleum, and the trustees are to rely on the visitor book in deciding if the grandchild satisfied the requirement. The trustees have no further duty to inquire and “shall have the right to presume that the [grandchild] did not visit the grave during that calendar year if [the grandchild’s] signature does not appear on the register for such calendar year.” This forfeiture provision will not apply if the trustees, in their discretion, determine a grandchild could not visit “by reason of physical or mental disability.”

While these provisions have been criticized as controlling, it seems unlikely that they would violate public policy. See Toobin, supra. Furthermore, the provisions appear sufficiently clear to avoid being invalidated for vagueness. Those drafting similar clauses may take away a few points—include exceptions when the restriction would no longer be appropriate (such as upon disability), be precise about the timing (such as clarifying that an annual requirement must be performed within each calendar year), and spell out how the trustees are to determine if the beneficiary met the condition.


On the probate side, Leona Helmsley merits the title Queen of Probate & Property because her will presents and addresses an astounding array of issues. For drafters, a recurrent lesson from her majesty’s will is the importance of anticipating post-death contingencies. Although few clients will have the wealth and personality of the Queen of Mean, many clients may appreciate a planner who can raise and address many of the concerns reflected in Leona’s will.