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Andy Warhol died on February 22, 1987, at New York Hospital in Manhattan, following complications from gallbladder surgery that was not supposed to be life-threatening. His will was, in one sense, remarkably simple: apart from modest bequests to his two brothers and to his longtime friend and business manager, Frederick Hughes, he left nearly everything he owned — tens of thousands of paintings, drawings, prints, and photographs — to fund a new foundation for the advancement

Tom Clancy spent a career rendering submarine specifications and defense technology with a precision so exact that the Navy reportedly wondered how a novelist knew them. His own estate plan was not written with the same precision. One ambiguous provision about which trust should bear his federal tax bill sent his widow and his four adult children from an earlier marriage into litigation that lasted three years and reached Maryland's highest court before anyone knew how much e

Gloria Vanderbilt died in 2019 at ninety-five, after a long life as a painter, a memoirist, and the designer who put her name on blue jeans. But the legal event that shaped her arrived when she was ten, in a Manhattan courtroom, in a proceeding she could not control. That is what makes her a useful planning example. Most estate planning focuses on who receives property. Her life is a reminder that the harder question is often who decides: who raises a child, who holds the mon

For four decades, Casey Kasem counted down America's favorite songs into millions of living rooms every weekend, his voice one of the most recognizable in the country. In the last eighteen months of his life, that same voice was, for practical purposes, unreachable to three of his own adult children, who spent afternoons standing outside his home holding signs because a piece of paper he had signed years earlier now decided who got to see him. How a family ends up on the wron

J. Seward Johnson Sr. died in 1983, and his family spent the next three years in litigation that ended without a verdict. The case is worth studying not for the size of the fortune but because the underlying situation is one estate planners see constantly at ordinary scale. An older person with substantial assets. A late marriage to a much younger spouse. Adult children from earlier marriages. A final will that changes who receives what. Estate planning is usually about decid

Doris Duke died in October 1993 leaving an estate worth more than a billion dollars, and the years that followed produced one of the most closely watched fiduciary disputes in modern New York practice. What makes it useful as a planning example is not its size but a single decision the will made. Duke named, as the one individual to serve as executor of that fortune, the man who had worked as her butler. Nearly everything after that traces back to the choice, and to a questio

Brooke Astor lived to 105 and spent most of her adult life giving money away. What makes her estate a useful planning example is not her fortune or the famous names attached to it, but her last decade, when the questions surrounding her became ones any family can face. Who decides when the client can no longer decide? Do documents signed late in life reflect what the client truly wanted? And what happens when the person closest to a declining parent is also the one who gains

Huguette Clark died in 2011 at the age of 104, having spent her last two decades in a Manhattan hospital room while three extraordinary homes sat empty and cared for. Her estate is a useful planning example, and not only for its size. Nearly every condition that makes a plan vulnerable appeared at once: great age, deep isolation, dependence on a small circle of caregivers and advisers, two conflicting wills signed weeks apart, and beneficiaries who controlled access to her. A

Marilyn Monroe died more than sixty years ago, yet legal and commercial questions connected to her estate have continued long after her death. That is what makes the estate useful as a planning example. For most people, estate planning is about deciding who receives property after death. But for clients with meaningful assets, complicated family relationships, valuable personal property, public visibility, or a strong sense of legacy, estate planning is also about preserving