Lessons from Tony Bennett’s Estate Battle

When legendary singer Tony Bennett passed away in July 2023, he left behind an estimated $100 million estate and, unfortunately, a family divide threatening to tarnish his legacy. His daughters Antonia and Johanna Bennett are now suing their brother, Danny, who serves as trustee of their father's estate, alleging a lack of transparency and potential mismanagement of assets. Let's explore what went wrong and how you can protect your family from suffering the same fate.

A complex legal battle is unfolding in the New York Supreme Court, where Tony Bennett's daughters Johanna and Antonia have filed suit against their brother Danny, who serves as trustee of their father's estate. The lawsuit raises alarming questions about the management of Bennett's assets. While the legendary singer earned over $100 million from live performances in his final 15 years, his daughters were told the estate was valued at less than $7 million.

The dispute centers around Danny's role as both trustee and former manager. In July 2022, Danny orchestrated the sale of Bennett's memorabilia, personal property, and name and likeness rights to Iconoclast, a company specializing in legacy works. The daughters allege they were kept in the dark about which assets were included in this deal and have received only "a modest distribution." They also claim Danny received $1.2 million in loans from their father in 2020 and lifetime gifts totaling $4.2 million - more than double what Bennett's other children received.

Making matters worse, when Johanna and Antonia were finally allowed to visit their father's apartment in 2024, they discovered many of his personal belongings were either missing or declared off-limits due to the Iconoclast sale. They learned that most of their father's clothing had been donated to charity without their knowledge, despite these items being specifically bequeathed to Bennett's children in the trust. An auction of Bennett's belongings was held in April 2024, but his daughters allege they were largely "kept in the dark" about the details and had to rush to identify which items they wanted to keep.

Court filings also state that the trust was established in 1994, but we don’t know if it was ever reviewed and updated over time. We also cannot know if Mr. Bennett was ever advised about the potential disputes that could arise from naming one of his children as his sole trustee and administrator of the estate.

A complex legal battle is unfolding in the New York Supreme Court, where Tony Bennett's daughters Johanna and Antonia have filed suit against their brother Danny, who serves as trustee of their father's estate. The lawsuit raises alarming questions about the management of Bennett's assets. While the legendary singer earned over $100 million from live performances in his final 15 years, his daughters were told the estate was valued at less than $7 million.

The dispute centers around Danny's role as both trustee and former manager. In July 2022, Danny orchestrated the sale of Bennett's memorabilia, personal property, and name and likeness rights to Iconoclast, a company specializing in legacy works. The daughters allege they were kept in the dark about which assets were included in this deal and have received only "a modest distribution." They also claim Danny received $1.2 million in loans from their father in 2020 and lifetime gifts totaling $4.2 million - more than double what Bennett's other children received.

Making matters worse, when Johanna and Antonia were finally allowed to visit their father's apartment in 2024, they discovered many of his personal belongings were either missing or declared off-limits due to the Iconoclast sale. They learned that most of their father's clothing had been donated to charity without their knowledge, despite these items being specifically bequeathed to Bennett's children in the trust. An auction of Bennett's belongings was held in April 2024, but his daughters allege they were largely "kept in the dark" about the details and had to rush to identify which items they wanted to keep.

Court filings also state that the trust was established in 1994, but we don’t know if it was ever reviewed and updated over time. We also cannot know if Mr. Bennett was ever advised about the potential disputes that could arise from naming one of his children as his sole trustee and administrator of the estate.

Like Mr. Bennett, many people select family members to administer their estate after they die. They trust family members and assume they’ll do the right thing. Or they haven’t been properly advised about the potential consequences of naming a family member as the estate administrator. However, as the Bennett lawsuit teaches, family members aren’t always the right people for the job. Here are several common issues that arise when family members serve as trustees:

Power Imbalance: Having one sibling control their siblings' inheritance creates an uncomfortable dynamic and breeds an environment of distrust. 

Dual Roles: Danny's position as both trustee and former manager created a potential conflict of interest. Questions about decisions and motivations often arise when personal and professional roles overlap.

Transparency Issues: The significant discrepancy between known earnings and reported estate value raises red flags about financial transparency – a crucial element of trust administration.

Emotional Complications: Family relationships can cloud judgment and make it difficult to maintain the objectivity required of a trustee.

If you’re concerned about family conflict after you die, consult with a trusted advisor who can educate you about the potential ramifications of your decision and guide you to choose the right person—whether a family member or not. As a Personal Family LawyerⓇ, my priority is helping you make the process as easy on your loved ones as possible and giving you peace of mind that you’ve done everything you can to keep your family out of court and conflict.

The primary way to prevent conflict in your family, after your incapacity or death, is to start courageous conversations with your family now. Conflict occurs when people are surprised about choices made by a loved one that are only revealed after it’s too late to gain understanding. Deep grief combined with surprise is a volatile combination. The best way to save your loved ones from this fate is to communicate often, and early. If you’ve created your plan with my office and desire me to host a family meeting, reach out and let’s get it scheduled. If you have not yet created your plan, let’s start there.

If for some reason, you do not believe you can get your loved ones on the same page, I sometimes recommend choosing a non-family member, or professional, as your Successor Trustee. A professional or corporate trustee, for instance, can provide the objective oversight needed to maintain family harmony while ensuring proper estate administration. In fact, this might have been a better choice for the Bennett family from the start.

However, if you strongly prefer having a family member serve as trustee, you can implement additional safeguards if you have an effective estate plan in place. An effective plan may include adding co-trustees or creating independent oversight mechanisms to help ensure transparency and accountability. It might mean appointing a professional advisor to review major decisions or requiring regular external audits of estate administration. 

Finally, make sure your chosen trustee has access to proper professional support. Managing an estate requires complex legal and financial knowledge that most family members don't possess. That’s why my Life & Legacy Planning process has built-in mechanisms to ensure your chosen representatives will always have help from me when they need it. But ongoing support for your family is rarely a part of a typical estate plan.

Creating an estate plan that truly protects your family requires careful consideration. It requires guidance on how to pick the right representative for you and your loved ones. It requires proper documentation of assets, including detailed records of everything from real estate to intellectual property rights. It requires clear distribution guidelines. It also involves transparency to help maintain family trust and prevent disputes from arising.

However, if you create a DIY plan, use a cheap online service, use a financial advisor who offers estate planning services, or if you work with a traditional estate planning attorney, these elements will most likely not be in your plan. Instead, you need a comprehensive Life & Legacy Plan that will work when you need it to.

When you work with me to create a comprehensive Life & Legacy Plan, I will help you:

• Choose the right trustee for your situation;
• Create systems for transparent asset management;
• Establish clear communication protocols;
• Protect family relationships from conflicts;
• Document your wishes on video or an audio file so your family understands precisely what you want;
• If you have minor children, gain peace of mind knowing that they will never be taken into the care of strangers if something happens to you; and
• Review and update your plan regularly to account for changes in family dynamics, assets, and life circumstances. 

We cannot know whether Mr. Bennett was advised of the potential consequences of naming his son to serve as trustee, or whether he was given proper guidance on what he could have done to keep his family out of court and conflict. But when you work with me to create a Life & Legacy Plan, I’ll support you to create a plan that leaves a legacy of love and peace, not discord and strife.

As your Personal Family Lawyer®, we help you create a comprehensive Life & Legacy Plan that protects your assets and preserves family harmony. We'll help you address potential conflicts before they arise, ensure your wishes are clearly documented, create a framework for managing your assets even if you become incapacitated, and be there for your chosen representatives when you cannot be. We’ll also review your plan with you on a regular basis so your plan works when you and your family need it to.

Don't leave your family's future to chance. Click here to schedule a complimentary 15-minute consultation to get started.

This article is a service of a Personal Family Lawyer® Firm. We don’t just draft documents; we ensure you make informed and empowered decisions about life and death, for yourself and the people you love. That's why we offer a Life & Legacy Planning Session™, during which you will get more financially organized than you’ve ever been before and make all the best choices for the people you love. You can begin by calling our office today to schedule a Life & Legacy Planning Session™.

The content is sourced from Personal Family Lawyer® for use by Personal Family Lawyer® firms, a source believed to be providing accurate information. This material was created for educational and informational purposes only and is not intended as ERISA, tax, legal, or investment advice. If you are seeking legal advice specific to your needs, such advice services must be obtained on your own separate from this educational material.

Proper estate planning can keep your family out of conflict, out of court, and out of the public eye. If you’re ready to create a comprehensive estate plan, contact us to schedule your Planning Session. Even if you already have a plan in place, we will review it and help you bring it up to date to avoid heartache for your family. Schedule online today.