“I left my heart” (and my family ripped it apart)

Just months after the legendary Tony Bennett passed away in 2023 at the age of 96, a bitter family feud erupted. His daughters, Antonia and Johanna Bennett, have filed not one, but two lawsuits against their older brother, Danny, who serves as trustee of their father’s trust and executor of his estate. Their accusations center on mismanagement, lack of transparency, and breach of fiduciary duty — claims that strike at the heart of what can go wrong when a family member holds too much control or abuses their fiduciary role.

According to court documents, Tony’s estate plan called for equal treatment among his four children, accounting for gifts and lifetime benefits. Yet the daughters claim they’ve received only $245,000 apiece — a stark contrast to the over $4 million Danny is said to have received while their father was alive. Meanwhile, Tony’s estate, initially valued at only $7–12 million, feels suspiciously low given a career estimated to have earned over $100 million — particularly during the singer’s final, high-earning years.

At the center of this conflict is Danny, who wore many hats: manager, power of attorney, trustee, and executor. While this may have made sense from a business standpoint, it arguably blurred the lines of duty, loyalty, and personal gain. Allegations suggest Danny engaged in self-dealing — benefiting from music catalog sales, memorabilia deals, and unchecked financial control, all while his siblings were kept in the dark.

This isn’t just another celebrity spat. It’s a cautionary tale about estate planning. When one sibling is placed in charge of distributing an estate to the others, especially in high-value or high-profile families, the result is often resentment, suspicion, and — all too often — litigation.

A proper estate plan must go beyond naming names. It requires foresight, transparency, and sometimes the wisdom to appoint an independent fiduciary who can manage affairs impartially. The cost of litigation, both financial and emotional, can deeply damage family bonds and diminish the very legacy a parent worked to build.

Tony Bennett gave the world unforgettable music. Hopefully, his estate battle will also serve as an unforgettable reminder: choose your fiduciaries wisely.

Evan J. Krame