What We Can Learn from Tony Bennett's Estate Dispute

Tony Bennett will be forever remembered for his unique, smooth, velvet voice. He began his career in the 1950s with the beginning of rock ’n’ roll with such artists as Bill Haley & His Comets, Elvis Presley and Bobby Darin. Bennett took a different path, focused on seemingly elegant vocals along with Frank Sinatra, Bing Crosby and Nat King Cole. Sinatra once said Bennett was the best singer in the world.

Bennett was diagnosed with Alzheimer’s disease in 2016. He died in July 2023 at the age of 96. His career took off in 1951 with his first big hit, “Because of You.”

His career was introduced to a new generation of fans in 2012 by Bennett’s performances with Lady Gaga and other contemporary artists. Lady Gaga (aka Stefani Germanotta) credits Bennett with helping her to reclaim her voice when she was recovering from hip surgery and chronic pain from fibromyalgia. They did two albums together that included duets of Bennett’s hits “I’ve Got You Under My Skin” and “The Lady Is a Tramp.”

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Bennett is thought to have earned more than $100 million in his lifetime, yet his estate at the time of his death is reported to have been only $7 million. Bennett is survived by his wife, Susan Crow, and his children D’Andrea “Danny” Bennett, Daegal “Dae” Bennett, Johanna Bennett and Antonia Bennett.

Forming the family trust

Tony Bennett created a trust in 1994, naming himself and his son Danny as co-trustees. The trust was funded at least in part. (Funding refers to the process of transferring the formal ownership or title to assets to the trust.) Susan, Antonia, Danny, Dae and Johanna were all listed as beneficiaries. Danny became the sole trustee upon his father’s death in 2023.

Johanna and Antonia filed a lawsuit in June 2024. In that suit, the sisters assert that Danny did not account for and disclose all trust assets and sales or other transactions involving trust assets. They also allege that Danny improperly received personal benefit from these transactions. Even if not true, there do appear to be significant conflicts of interest and the potential for the exertion of undue influence by Danny.

Danny was not only a co-trustee, but he was also his father’s manager. Tony Bennett formed Benedetto Arts, LLC to hold certain property and assets. His children and the family trust held membership interests in the LLC. Danny was also a manager of the LLC.

Bennett’s will provided that any tangible personal property not transferred to the trust was to be distributed to his children equally. For most of us without substantial art collections, jewelry or similar collectibles, tangible personal property often has little value. However, for celebrities with “star power” such as Tony Bennett, property, pictures and assets bearing their likeness often have substantial value. In fact, the disputes over Robin Williams’ estate involved similar items of personal property.

What Danny allegedly did

In July 2022, before Tony Bennett’s death but well after his diagnosis of Alzheimer’s disease, Danny sold items of his father’s memorabilia and his name and likeness. Danny allegedly received a substantial commission on that sale through his company, RPM Productions.

Danny also allegedly sold at auction items of Tony’s personal property without appropriate disclosure and notice to Johanna and Antonia. Inherited items of personal property can often hold substantial sentimental value for children or other heirs. For example, my father was in the Navy and had glass beer mugs with a gold stripe at the rim and different Navy signed flags on the side. I first saw those when I was about 4 years old, and the mugs were not used often — with nine kids, my parents did not entertain much. Those mugs had a much greater emotional value to me than to my siblings. Johanna and Antonia may have had similar feelings about some of their father’s assets.

Danny allegedly received loans in 2020 (after Tony’s Alzheimer’s diagnosis in 2016) totaling $1.2 million. While all of Tony’s children received gifts, Danny also received a 25% commission for certain work that he performed with his father.

Everyone loses in a trust contest or related litigation. Substantial legal and professional fees are often incurred. More important, family relationships are often fractured, with little hope of ever healing.

What we can learn from this

What can we learn from Tony Bennett’s estate plan and administration to help prevent such litigation or disputes within our own families?

Lesson #1: Transparency and open communication are crucial.

Failure to communicate is almost certainly the biggest trigger causing estate and trust litigation. Once it begins, litigation can develop its own, very expensive, energy or weather pattern. The litigation can feed on itself, resulting in a substantial reduction in the value of the assets actually transferred to your children or loved ones. Each beneficiary needs to retain counsel typically. The trustee needs a lawyer to represent them as the trustee and potentially a different, independent lawyer to represent them as a beneficiary. With that many lawyers, substantial costs will be incurred.

Lesson #2: Consider a professional or corporate trustee.

With the potential size or value of the estate involved (almost certainly in excess of $7 million and up to $100 million) and the complicated nature of the transactions, a corporate or professional trustee should have been considered. The forgoing narrative or story illustrates many situations where Danny had a conflict of interest as a trustee, a manager of the LLC and as Tony’s manager. 

Those concerns were substantially increased as Tony lost competency due to Alzheimer’s. Even if Tony was competent for some of the transactions, he may have been more susceptible to undue influence or coercion. The use of an independent, professional trustee would have provided substantial protection for the beneficiaries and for Danny as the trustee. 

Professional trustees are typically highly trained, with significant experience and outside resources to provide the best possible guidance and assistance in achieving the family’s goals and objectives.

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