Posted in Triplett & Carothers on October 3, 2025

Tony Bennett died in July 2023 at age 96 after a long career and a yearslong public battle with Alzheimer’s disease. His estate plan named his eldest son, D’Andrea “Danny” Bennett, as trustee. Danny was also his longtime manager and had held power of attorney. Less than a year after Bennett’s death, two of his daughters, Antonia and Joanna, filed a lawsuit accusing Danny of mismanaging the estate. Another brother, Daegal Bennett, and Bennett’s widow, Susan, were named as defendants in the litigation as well. A second lawsuit followed in 2024.

A trust doesn’t prevent conflict, transparency does

The sisters say that Bennett’s trust, originally created in 1994, required equal treatment of all four of his children. But in the first lawsuit, they claimed that Danny, acting as trustee, acted without transparency. The second lawsuit went further, accusing him of self-dealing, breach of fiduciary duty and unjust enrichment both before and after their father’s death.

The lawsuits focus on Danny’s 2022 sale of Bennett’s name, likeness, memorabilia and personal property to Iconoclast, a legacy management company. The daughters claim they weren’t informed of the terms or even which assets were included. They also allege that Danny received $1.2 million in loans from their father in 2020 and $4.2 million in lifetime gifts, significantly more than the other children received.

Danny has long been credited with his father’s late-career success. But that overlap between personal loyalty and business control now raises legal questions. Danny’s dual role as former manager and trustee complicates whether he acted only in the best interest of the estate.

Did Bennett know? And did it matter?

Allegations of undue influence and diminished capacity are central to the dispute. The sisters argue that in his later years, their father may not have fully understood the deals being made on his behalf. If they can prove that Danny acted against Bennett’s best interests or used his influence to benefit himself, they may succeed in having him removed as trustee. Additionally, he may owe damages to the estate.

The legal filings also challenge the reported $12 million value of Bennett’s estate. The sisters say they each received $245,000, but they argue that doesn’t reflect what their father earned — live performances during his final 15 years reportedly brought in over $100 million. They argue that something doesn’t add up.

A neutral trustee might better have prevented this

Naming a family member as trustee is common, but it doesn’t always serve the family well. Trustees are held to high legal standards: They must act solely in the interest of all beneficiaries and keep clear, open records. This is harder to do — or perhaps harder to believe that it is being done honestly — if the trustee is a sibling, especially one with financial control or personal history.

If a family member is named, safeguards can include naming a co-trustee who is not part of the family or establishing regular oversight by an outside adviser. A review process or audit requirement can also help prevent or resolve concerns about fairness.

Bennett trusted Danny with his business and personal affairs during his life, but that doesn’t guarantee the other heirs would agree after his death. An independent third-party trustee can help avoid family drama and discord.