Celebrity estate disputes rarely make headlines based solely on the estate’s high value — though wealth often plays a role. More often, they capture attention for revealing the complex family dynamics that can emerge after a loved one’s passing, affecting inheritances and sparking emotional turmoil.
The ongoing legal battle over Tony Bennett’s estate is a prime example. The beloved singer, whose career spanned from the 1950s until his death in July 2023 at age 96, entrusted his eldest child, Danny Bennett, with managing his assets and carrying out his estate plan — as both executor of his estate and trustee of his trust, according to Rolling Stone.
However, an April 2025 lawsuit filed by Bennett’s daughters, Antonia Bennett and Johanna Bennett, alleges that Danny may be exploiting his position for personal gain at the expense of other beneficiaries. They accuse him of withholding critical information, making questionable decisions, disregarding their father’s known wishes and generally mismanaging the estate.
Though it might seem that legal battles over multimillion-dollar celebrity estates are far removed from everyday concerns, the underlying legal issues are surprisingly common. Families managing estates — large or small — often face similar challenges of trust, transparency and power imbalances.
This dispute underscores a common issue: When one family member holds disproportionate authority, it can leave other beneficiaries feeling powerless and may open the door to potential abuse of that power. The Bennett estate case exemplifies this imbalance, as the sisters have reportedly received only modest inheritances compared to their brother’s sizable share — despite Tony Bennett’s expressed wish that his assets be divided equally among his children.
Fortunately, there are legal remedies available to address such imbalances — through probate proceedings or court intervention — that can help restore fairness and accountability to the process.
“While appointing a family member as trustee often makes sense, it can create a power imbalance that breeds conflict and erodes trust,” explains Roee Kaufman, a partner at Keystone. “In the Bennett family’s estate case, placing one sibling in control of the inheritances of the others may not have been the best decision, as the resulting conflict clearly shows.”
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What We Know About the Battle Over Tony Bennett’s Estate
While the court documents filed in the Tony Bennett estate dispute offer some insight into the musical legend’s estate planning, limited information has been publicized, making it difficult to draw fully informed conclusions about the case.
That said, here’s a rundown of what we know so far:
Estate Roles and Relationships
During Tony’s lifetime, his son Danny served as his longtime personal and professional manager, attorney-in-fact and trustee. Antonia and Johanna are beneficiaries of their father’s estate and trust, along with their brother Dae Bennett and their father’s widow Susan Bennett, reports NBC News.
Prior Lawsuit
In June 2024, Antonia and Johanna filed a lawsuit against Danny, alleging that he was mishandling their father’s assets and demanding transparency. According to NBC News, they specifically were seeking a full accounting of their father’s estate.
As of now, that case has not been publicly resolved and appears to be part of the ongoing legal dispute, which escalated with the more detailed April 2025 lawsuit.
New Accusations
In April 2025, Antonia and Johanna filed a follow-up lawsuit alleging that Danny exploited his multiple fiduciary roles to wrongfully enrich himself both before and after their father’s death at the expense of their father’s wishes and the other beneficiaries. According to NBC, Dae and Susan are also named as defendants in the lawsuit.
Danny is accused of taking advantage of Tony’s declining mental state due to Alzheimer’s to orchestrate multimillion-dollar transactions benefiting himself and his business interests. Notably, shortly before Tony’s death, Danny sold the jazz legend’s music catalog, as well as his name, likeness and image rights, to the entertainment IP and brand management firm Iconoclast.
According to the lawsuit, Danny engaged in “self-interested and conflicted transactions,” earned “excessive and unearned commissions” and made “substantial loans and gifts to himself and his children,” depleting assets that Tony’s will specifically directs to be divided equally among his four children.
The sisters also claim that Danny disposed of items of significant sentimental value in a “malicious and retaliatory manner” in response to their previous lawsuit seeking an accounting.
“Tony maintained a loving and devoted relationship with all of his children, and his estate plan expressly provides that all four children be treated equally, including through provisions to equalize each child based on benefits Tony conferred on them during his life,” the sisters state in the lawsuit.
The court documents continue: “Since Tony’s death, Johanna and Antonia have discovered that Danny exercised complete and unchecked control over Tony and his financial affairs both before and after his passing through multiple fiduciary and other authoritative roles — roles that Danny has abused, and continues to abuse, for his own substantial financial gain.”
The ongoing lawsuit seeks damages to be determined at trial, as well as Danny’s removal as trustee.
Why Are Tony Bennett’s Daughters Suing Their Brother Over Allegedly Mishandling Their Father’s Estate?
The Tony Bennett estate dispute revolves around questions of fairness and transparency. Namely, Antonia and Johanna have reportedly received only modest distributions, while their brother has benefited substantially both before and after their father’s passing. This is particularly troubling to the daughters, given Tony’s clear intention in his will for his children to inherit equal shares.
In the following sections, we explore the key issues fueling the Tony Bennett estate battle.
Discrepancy Between Reported Earnings and Value of Estate
To date, Antonia and Johanna have each received only a “single modest distribution” of $245,000, despite the estate being valued at $12 million at the time of Tony’s death, and his lifetime earnings exceeding $100 million — including significant income during the final decade of his career. The lawsuit claims the sisters “have not received any credible explanation about what happened to Tony’s substantial lifetime earnings prior to his death.”
The significant disparity between the benefits Danny has received — an estimated $4.2 million in gifts from Tony over the years, according to Yahoo — compared to Antonia’s and Johanna’s benefits has raised suspicions of self-dealing, with the sisters arguing that the estate’s reduced value clearly indicates mismanagement or an unauthorized depletion of assets.
“Tony’s daughters have legitimate concerns, and the disparity in distributions raises red flags,” says Shawn Kerendian, managing partner at Keystone. “However, without a full review of the estate plan and financial records, it’s premature to conclude misconduct. The lack of transparency is troubling, but smaller distributions alone don’t prove mismanagement — factors like significant estate debts can also reduce the assets that are available to estate beneficiaries.”
Potential Conflict of Interest
A common question in estate disputes is whether an executor or trustee can also be a beneficiary — and if doing so risks undermining the fair and proper administration of an estate. Similarly, can someone with power of attorney make financial decisions on behalf of the principal that benefit themselves? These potential conflicts of interest are central to the Tony Bennett estate battle.
The answer is yes — a trustee or executor can be a beneficiary, and a person with power of attorney can make financial decisions that personally benefit them, so long as the POA document authorizes them to do so, and their actions do not breach their fiduciary duties.
In fact, it’s not unusual for family members to serve in these roles. However, those appointed must act impartially, ensuring they do not prioritize their own interests over those of the other beneficiaries. Their fiduciary duties require them to administer estates fairly and transparently.
In the Bennett case, Danny epitomizes this conflict: He is both a beneficiary and holds (or has held) key fiduciary positions, including power of attorney, trustee of the family trust and executor of the estate, managing his father’s affairs both before and after his passing.
Holding these overlapping roles places Danny in a position of significant control over decisions impacting the estate and all its beneficiaries, including himself and his sisters. Given that Danny’s financial benefits have reportedly amounted to millions — far exceeding the distributions received by his sisters — it raises serious questions about whether his actions primarily served the estate’s collective interests or his own.
Court documents allege that Danny used his authority to enrich himself and his business interests at the expense of the other beneficiaries. Specific claims include receiving excessive commissions, taking out two loans totaling $1.2 million and making gifts to himself and his children — all without informing or consulting his sisters.
“Conflicts of interest frequently trigger family disputes, especially when a relative acts as trustee or executor,” explains Kaufman. “Without strict adherence to fiduciary duties — such as loyalty, impartiality and transparency — the estate administration can become compromised, undermining the fairness of the process.”
While a potential conflict of interest alone is not inherently problematic, it can become an issue. Effective checks and balances are critical, but according to the lawsuit, Danny has not made this easy for his sisters. Allegedly, he’s failed to fulfill his duty to disclose key information.
Failure to Disclose Information to Beneficiaries
When a fiduciary — such as a trustee or executor — fails to provide clear information about their actions or transactions involving estate funds, beneficiaries often suspect the lack of transparency is intentional and aimed at hiding misconduct.
In many cases, their concerns are justified. Any fiduciary familiar with their legal obligations understands that disclosing key information to interested parties isn’t just a requirement; it is one of their most essential duties. Without such transparency, beneficiaries may remain unaware of what they are entitled to, when distributions might occur and other essential details needed to protect their inheritance and assert their rights.
Danny’s reported lack of transparency has been a central point of contention in the Tony Bennett estate dispute. In both lawsuits, his sisters accuse him of failing to provide adequate accounting of estate expenses and transactions. Notably, they claim he withheld important information regarding the sale of Tony’s music catalog.
According to the lawsuit, “Johanna and Antonia had little or no knowledge of the Iconoclast deal at the time it occurred,” “were given no indication or information that such a deal was even being discussed prior to its occurrence,” and continue to lack complete details about the net proceeds and circumstances of the sale.
In response, Danny has argued that his sisters lack the legal authority to access financial records from before or after their father’s death. His attorney maintains that preparing an accounting for an estate that’s only been open a year is burdensome and unnecessary.
Danny is still withholding records, claiming that his father intended for him to have sole control over the trust, reports Yahoo. He also suggests that his sisters are confused because their father frequently gave him and his wife significantly more gifts than he gave them.
“While a thorough review of the estate plan is necessary to determine if Danny has breached his duties, some of his and his attorney’s statements raise red flags,” Kerendian observes. “Annual accountings are standard practice and required by law when requested by an interested party. Even if a trustee has sole control over a trust, that does not absolve them from the duty to keep beneficiaries reasonably informed.”
Although what constitutes reasonable communication may be subjective, Danny’s failure to disclose the multimillion-dollar Iconoclast deal to the sisters — who are directly impacted — is concerning. Transparency on such consequential transactions is not just reasonable; it is expected.
Undue Influence and Capacity Concerns
Although the lawsuit does not appear to explicitly allege undue influence, the claim is strongly implied. According to NBC10 Philadelphia, Antonia and Johanna assert that Danny took advantage of their father’s diminished mental capacity from Alzheimer’s disease — which was diagnosed in 2016 — to secure multimillion-dollar deals benefiting both his company and himself.
One such example is the Iconoclast deal, which Danny brokered after Tony’s diagnosis and shortly before his death. While his power of attorney may have legally authorized him to proceed, that authority does not guarantee the transaction was in Tony’s best interests — or in those of the trust beneficiaries, including his sisters.
Advanced Alzheimer’s generally leaves an individual unable to make legally binding decisions and more susceptible to undue influence, fraud and other forms of exploitation.
Undue influence occurs when someone exerts excessive pressure on another person, overriding that person’s free will to serve their own objectives. In probate disputes, it is often alleged when a vulnerable adult is persuaded to create, change or revoke an estate plan in a way that benefits the manipulator.
If it can be proven by a preponderance of the evidence, undue influence can be grounds for contesting a trust or will. However, in this case, it appears unlikely that the sisters are formally pursuing this claim, given that the reported pleadings do not suggest the trust’s validity is being challenged and the statutory deadline for bringing a contest may have already elapsed.
Missing or Damaged Personal Property
Executors and trustees have a fiduciary duty to protect and preserve the assets under their control. This way, when assets are distributed to beneficiaries, they will not have suffered a significant loss in value. Antonia and Johanna allege in their lawsuit that Danny failed to uphold this responsibility.
According to the sisters, valuable personal artifacts from their father’s decades-long career — including memorabilia, awards and other sentimental items — have either gone missing or been damaged on Danny’s watch. These items, they argue, carry not only deep emotional significance but also substantial monetary value.
The lawsuit further claims that Danny restricted their access to their father’s apartment for a considerable period after his death. Antonia was reportedly promised Tony’s piano, but when she was finally allowed inside, she found it in “terrible condition,” according to NBC10 Philadelphia.
While estate disputes often focus on financial accounts and investments, the mishandling of valuable personal property — especially when it appears to have been neglected, sold without transparency or intentionally damaged — can expose a fiduciary to personal liability.
If the court finds that Danny acted negligently or, as the sisters allege, disposed of property in a “malicious and retaliatory manner,” he could be required to reimburse the estate from his own funds.
Tony’s will also reportedly directed that any tangible personal property not held in his trust be divided equally among his four children. Although trustees and executors may sell property, they must account for and distribute the proceeds according to the terms of the will or trust.
The sisters allege they have not been informed about what happened to certain property, have not received the proceeds from sales, or have been given items in poor condition — all of which may suggest misconduct. If Danny kept any proceeds for himself or his family, it would amount not only to self-dealing but also to a direct violation of the will’s instructions.
How the Tony Bennett Estate Dispute Could Play Out
Because so few details have been made public about Tony Bennett’s estate plan, the terms of his trust or the evidence his daughters have gathered, it’s impossible to predict with certainty how this dispute will unfold.
However, the remedies outlined in their lawsuit give some insight into the possible legal outcomes if the matter proceeds to trial.
Trustee Is Ordered to Disclose Information
If a trustee fails to keep beneficiaries informed, beneficiaries are entitled to petition the court to compel disclosure. If the court deems the request reasonable, it will typically order the trustee to produce the information by a set deadline.
Trustees who lose such a petition may also be ordered to pay the beneficiaries’ legal fees, which is why most fiduciaries comply with information requests before the situation escalates.
Before involving the court, beneficiaries should attempt to make their requests for information directly with the trustee — ideally in writing to create a paper trail. This documentation can be valuable if legal action becomes necessary.
If the trustee’s failure to disclose information isn’t an isolated incident but part of an ongoing pattern, the court may impose more serious remedies — including suspension or removal.
Removal and Surcharge of the Trustee
The sisters’ lawsuit seeks Danny’s removal as trustee, alleging misconduct. Danny disputes these claims and maintains he acted within his authority.
Even if the accusations are not proven, the court could replace him as trustee if his conflict with the beneficiaries is preventing effective estate administration. In some cases, the trustee may be suspended, with an interim trustee being appointed, while the matter is investigated to prevent further harm to the estate. The court also has the power to impose a surcharge — a financial penalty requiring the trustee to repay losses caused by their actions.
In addition, the sisters are seeking damages for the losses Danny allegedly caused to the estate, though the amount will be determined at trial.
If the matter goes to trial, the prevailing party may seek attorney’s fees and costs from the opposing side, but such awards are not guaranteed.
Out-of-Court Settlement
In probate disputes, settlements are far more common than trials because they typically save time, reduce costs and minimize emotional strain.
“Whether an out-of-court settlement will be sought in this case likely will depend on the degree of conflict between Danny and his sisters, as successful negotiations require all parties to be willing to compromise,” explains Kaufman. “If neither side is willing to budge, settlement may not be possible.”
Even though both parties may possess the financial means to litigate to trial, Danny, as trustee, may have the power to use trust assets for his legal defense, whereas his sisters would need to fund their own. However, if the claims against him are successfully proven, he may have to reimburse the trust for his attorney fees and costs.
Another risk of prolonged litigation concerns the depletion of estate assets before they are distributed, which would be a poor outcome for all beneficiaries.
Important Takeaways From Tony Bennett’s Estate Lawsuit
Even though it may seem there’s not a lot to learn or relate to from a celebrity’s multimillion-dollar estate battle, it does actually shed light on real legal issues everyday people encounter as well — and may even provide insight into how such conflicts can be resolved.
While this lawsuit stresses the importance of nominating a neutral executor or trustee to serve in order to prevent disputes, there are also other important takeaways to consider.
Incapacitated persons may benefit from a conservatorship.
Although Tony had granted Danny power of attorney to manage his finances, this may not have been the wisest choice given his son’s personal financial interests in those assets and the resulting conflict of interest.
Since 2016, Tony had advanced Alzheimer’s disease — a grave diagnosis that would have severely impaired his ability to handle personal and financial matters. While a power of attorney can be useful, it is not subject to the same level of oversight as a conservatorship.
A court-supervised conservatorship generally offers greater protection against abuse because it requires regular accountings and court oversight.
Tony’s vast wealth and complex asset portfolio made transparency even more critical. Under a conservatorship, questionable transactions — such as unauthorized gifts, self-dealing or undervalued asset sales — are far more difficult to conceal.
In situations involving incapacitated individuals, especially those with substantial estates, court oversight can be the safeguard that prevents irreversible loss.
While conservatorships can be restrictive, for someone with advanced Alzheimer’s, they may be the only effective mechanism for managing that person’s personal and financial affairs and protecting their assets.
Powers of attorney are available only to those with capacity; once capacity is lost, a conservatorship may not just be preferable — it may be the only viable option.
Beneficiaries must actively seek information.
Beneficiaries should remain actively involved in the administration process, even if the trustee or executor makes it difficult to obtain information. A hands-on approach helps ensure the estate is managed properly and reduces the risk of mismanagement going unnoticed.
The sisters in this case took the right legal steps to challenge their brother’s lack of transparency, but many beneficiaries delay action until obvious problems emerge — by which time they may not be easy to fix. For instance, if an executor’s potential misappropriation is only discovered after the court issues a final distribution order, there may be no legal recourse available.
This case underscores the need for consistent oversight of fiduciaries — regardless of whether they are a trusted family member. Beneficiaries should review all inventories, accountings and financial documents as soon as they are provided and press for clarification if something seems unclear or inconsistent. Having an attorney review these documents can be invaluable, as they are often better equipped to identify irregularities or red flags.
Had the sisters simply trusted the process and not monitored the estate’s administration, the alleged misconduct could have caused irreversible harm, leaving them with even smaller inheritances than they anticipated.
Appointing a family member as trustee often comes with risks.
While it may seem natural to appoint a sibling, parent or other relative as trustee or executor, doing so can introduce unique challenges. Family members with control over an estate or trust — particularly when they stand to inherit from it — may face real or perceived conflicts of interest.
By contrast, a neutral, private professional fiduciary has no personal stake in the estate and can often administer it more efficiently, without the complications of family dynamics.
Importantly, a family member who has been appointed to a fiduciary role can decline the position or resign if a conflict of interest could compromise their ability to remain impartial. While relinquishing control may feel like a loss, it can spare them the risk of personal liability for breaching their fiduciary duty.
“People often assume their assets are safest under the control of family members,” Kerendian says. “While this can be true, power imbalances and competing interests can sometimes create more conflict than if a neutral professional were appointed instead.”
Concerned about trustee or executor misconduct?
Trustees and executors wield significant authority over estate assets — often with little day-to-day oversight. This power can be misused, whether intentionally or through mismanagement, as the Bennett case may end up proving. Even honest, well-intentioned individuals can be tempted or pressured into wrongdoing.
If you are a beneficiary, having a probate attorney involved from the start can help safeguard your inheritance. An attorney can monitor the administration, review financial records, explain your rights and quickly intervene if disputes arise.
At Keystone, we help clients hold fiduciaries accountable. Don’t leave your inheritance to chance — call us today to learn how we can protect your interests.
