The Big Lesson From Tony Bennett’s Embattled Estate and Troubled Trust

Just this week, a headline about the battle over Tony Bennett’s estate caught my attention.  I started reading and discovered that Tony’s daughters have initiated a second lawsuit against their brother and the idea for this article was born.  Fights over celebrity estates usually involve one lawsuit, two separate lawsuits may signal evolving issues or particularly egregious behavior.  Celebrity estates come in various forms and often provide important lessons for Estate Planners.  Sometimes the estates remind us that proper planning is paramount, other times they prompt us to update an Estate Plan regularly to account for changes in beneficiary circumstances, occasionally, they remind us to review execution and validity requirements, and sometimes, like here, they illustrate the importance of naming the right individuals to undertake the responsibility of administering an Estate or Trust.  Let’s see what lessons unfold from the legal drama surrounding the estate of Anthony Dominick Benedetto, known professionally as “Tony Bennett.”

Tony Bennett died on July 21, 2023, at the age of 96 after a lifetime of prestigious awards, an undeniable impact on music, and a prolific career.  An embittered battle over his Estate and Trust threatens to mar that legacy.  At the time of Tony’s death in 2023, estimates indicated that his earnings from live performances during his last fifteen (15) years of life alone netted him $100 million.  That amount should provide amply for his surviving spouse and four (4) children.  Sources make clear that Tony created an Estate Plan, although the details of that plan remain relatively secret.  The public facts about the Estate Plan reveal that Tony named his eldest child, D’Andrea (“Danny”) Bennett, to serve as Trustee of the Trust and as Executor of the Estate and that he was to equalize the amounts distributed to the children to provide each with an equal amount after adjusting for the gifts and benefits Tony gave them during his life.  According to sources, Antonia and Johanna Bennett have received $245,000 from the Estate and Trust while Danny netted over $4 million from his father during life, not exactly equal treatment.

Not long after their father’s death, Antonia and Johanna Bennett filed a lawsuit against Danny alleging that he withheld information about the assets of the Estate and Trust and failed to account for sales of Tony’s music catalog and image rights proceeds.  They sought equitable relief and a full accounting of all assets of the Estate and Trust.  Antonia and Johanna named their brother, Daegal (“Dae”) Bennett, and Tony’s widow, Susan Benedetto, in the lawsuit as well.  According to the first lawsuit, Danny valued their father’s estate at $7 million, a number far below that $100 million estimate.  Sources do not clarify whether that includes amounts in Tony’s Trust, the terms of which remain private.  The lawsuit alleged that Danny provided piecemeal information and documents that raised more questions than they answered.  Finally, the lawsuit accused Danny of benefitting from the sale of the memorabilia on a personal level.  Less than a year after filing the first lawsuit, Antonia and Johanna filed a second lawsuit alleging mismanagement of finances, breach of fiduciary duty, and unjust enrichment.  The lawsuit seeks to remove Danny as Trustee and asks for damages resulting from Danny’s “unchecked control” of their father’s finances and his abuse of power for his own gain.  The lawsuit contains several other serious allegations which will play out in the public eye.

Fiduciaries represent the cornerstone of any decent Estate Plan.  They have several responsibilities to fulfill in administering both the Estate and Trust, including marshaling the assets; making decisions regarding the investment and distribution of assets; and potentially undertaking litigation. Fiduciaries may have to appear in court and liaise with the attorney handling the Estate and Trust.  In fulfilling these obligations, fiduciaries need to adhere to the highest ethical standards and fiduciary duties.  Of all the responsibilities that fall under the umbrella of fiduciary duties, that of loyalty tops the list in importance.  The duty of loyalty obligates the fiduciary to consider beneficiary interests first, ahead of their own, and refrain from exploiting the office for their own benefit.  Most judges view allegations of breach of these duties seriously and impose steep penalties for a breach.  Danny occupied a unique position as his father’s manager that gave him significant access and influence and it may have been tough for Danny to transition from manager to fiduciary.  The pleadings make these allegations, but evidence has yet to emerge, either way.  The lawsuits make clear, though, that Danny’s sisters suspect wrongdoing.

As this case demonstrates, choosing the proper fiduciary makes or breaks an Estate or Trust.  Particularly in a Trust, one sibling serving as Trustee for another often spells disaster, breeds resentment, and damages the relationship irrevocably.  Parents mean well when they name one child to serve as Trustee of a Trust for the benefit of another, but all too often that causes friction because one child feels like they need to ask the other for their inheritance.  Tony’s situation, however, sounds like more than that. Danny’s long-time position as manager could have sowed the early seeds of discord with his sisters and naming him to serve as Trustee may have only deepened that divide.  His alleged lack of transparency may have been all that Antonia and Johanna needed to opt for litigation and that’s unfortunate.

Yet again, we have a front-row seat to a family imploding.  We have no way of knowing whether anyone counseled Tony regarding the inherent dangers in naming one child as Trustee for another or whether he knew and decided to name Danny in that position regardless.  Further, it’s unclear whether assets exist outside the Estate, whether Danny has breached his fiduciary duties, or whether his sisters are simply tired of waiting for their inheritance.  What this case makes clear aside from exercising caution in naming a fiduciary is the importance of consulting with me to help you consider these and other issues in your own Estate Plan.  Reach out today!