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!

A Hole in Hackman’s Plan

Eugene (“Gene”) Allen Hackman amassed an $80 million fortune over the course of his prolific acting career that spanned several decades. Yet, despite his fame, fortune, and an Estate Plan, his estate may end up in litigation because of incomplete planning. In a story with twists and turns as bizarre as some of the movies in which he starred, Gene Hackman died on February 18, 2025. When the news first broke that Gene and his wife of thirty-three years, Betsy Arakawa (“Betsy”), died in their Sante Fe home on February 26, 2025, many were shocked. Local authorities determined that the circumstances surrounding their deaths warranted investigation. Earlier that day, two maintenance workers found Gene and his wife unconscious inside the home. A subsequent telephone call to 911 revealed that neither was breathing and the authorities later discovered both had been dead for some time. The facts surrounding their tragic deaths give us reason to pause, as does their Estate Plan.

Gene Hackman got his start on Broadway and starred in movies too numerous to count playing roles that ran the gamut from kindly coach to venomous villain. He was a natural in every role as his many accolades evidence. He had three children, Christopher Allen, Elizabeth Jean, and Leslie Ann Hackman, with his first wife, Faye Maltese (“Faye”). Gene and Faye divorced after thirty (30) years of marriage and five (5) years later he married Betsy and remained married to her until her death a week before his. Authorities believe that because Gene was suffering from advanced-stage Alzheimer’s he was unable to comprehend or alert anyone to her death. Imagine the iconic Gene Hackman spending his final week alone, confused, and unable to care for himself. What a tragic end to an otherwise magnificent life.

Normally, when this blog examines celebrity estates it’s because litigation has begun. For the respective estates of Gene and Betsy, that hasn’t happened yet, although Gene’s son has already hired a litigation attorney. Here, both Gene and Betsy had Estate Plans and yet, many of the terms of those plans have not been made public, although it seems both plans left all assets to Gene’s Revocable Trust. Gene’s Trust named Betsy as beneficiary, but it seems did not complete a scenario in which she died first. While some sources report that Gene’s Will didn’t mention his children, others indicate that he created trusts for their benefit, yet none confirm that Gene’s Trust named his children as beneficiaries upon Betsy’s death or upon her predeceasing Gene. That’s a common way to structure an Estate Plan in a second marriage situation, especially when one spouse has children from a prior union. Yet that did not happen here, which makes that lack of planning more surprising. Conversely, Betsy’s Estate Plan not only required Gene to survive by ninety (90) days but also inserted alternate beneficiaries if he failed to survive her. Gene did not survive Betsy by the necessary amount of time, thus it’s unclear whether Betsy’s assets will pass to Gene’s Trust, to charity as dictated by her Estate Plan, or in another way.

As is so often the case with celebrity estates, we can learn lessons from what went wrong. Betsy functioned as caregiver for Gene which often happens when one spouse takes ill. What struck me, though, was that Betsy had no outside help and neither she nor Gene had set up any other support system for Betsy. They had the means to hire help yet failed to do that. Even if a loved one insists upon shouldering the burden of care alone, a system of “check-ins” provides invaluable support and an opportunity for updates without being too intrusive. An established well-check needn’t be anything extensive. A text or call to ensure that the other party answers and doesn’t need assistance will suffice. Here, that may or may not have made a difference. Given Gene’s advanced Alzheimer’s diagnosis, it sounds like he was unable to communicate at all, but a lack of response from him or Betsy may have alerted someone that something was not right.

Next, ensure that your Estate Plan contains contingency plans that cover not only the appointment of fiduciaries but also beneficiaries. Your Estate Plan needs to contain provisions for the appointment of fiduciaries and successor fiduciaries, as well as a method to appoint additional fiduciaries should none of the named individuals be able to act. The plan also needs to cover as many potential outcomes as possible. Here, Betsy’s plan had clear instructions regarding what should happen should she outlive Gene which was a fair assumption given their age gap. Gene’s plan, however, had a significant hole in failing to address what should happen should Betsy predecease Gene. While that was an unlikely scenario, it was the correct one here. Gene could have easily inserted his children as the backups to Betsy which often occurs, especially in a second marriage situation. He could have named a charity or other individuals as well. Most states have statutes that dictate how assets pass in the absence of clear provisions in an Estate Plan, and it could be that those laws govern here.

Though the incomparable Gene Hackman has left this earth, his legacy will live on and the curious may gain a deeper understanding of the man behind the myth as this plays out in a public forum. Don’t leave your final plans undone. Reach out to me to ensure that your Estate Plan contains the proper contingencies…and don’t forget to check on your loved ones!