Dead Celebrity

WealthManagement.Com

Welcome to the Dead Celebrities podcast. In this podcast we break down high profile celebrity estate planning cases for advisors and their clients. Most celebrity estate catastrophes are based on the same issues that everyday people face, just with the volume turned up. Our goal is to identify and extract the individual estate planning issues that lie at the heart of each story. We then discuss what advisors should expect and how to avoid common pitfalls.

  • 22 minutes 54 seconds
    Celebrity Estates: Lessons from Rob Reiner’s Estate

    Unexpected events can expose gaps in even the most carefully prepared estate plans.

    When family conflict, legal standards and timing collide, the outcome can reshape how assets move and who ultimately benefits.

    In this episode of Celebrity Estates, Senior Editor David Lenok examines the estate of Rob Reiner alongside Sean Weissbart, partner and co-chair of the Tax Benefits and Private Client Practice Group at Blank Rome. The conversation focuses on how slayer statutes function, why probate courts rely on civil standards rather than criminal convictions, and how intent and mental state influence inheritance outcomes.

    Sean explains how being treated as predeceased can redirect assets, how insanity defenses may affect eligibility and why simultaneous death rules and community property laws matter when spouses die close in time. 

    Join David Lenok and Sean Weissbart as they break down the estate planning lessons behind rare legal scenarios and the importance of thoughtful planning when the unexpected occurs.

    Key takeaways:

    • How slayer statutes prevent financial benefit after intentional and felonious killing
    • Why civil standards of proof differ from criminal convictions in estate matters
    • How predeceased treatment redirects inheritances to alternate beneficiaries
    • The role of insanity defenses, trusts and fiduciaries in inheritance outcomes
    • Why simultaneous death provisions and planning details can reshape asset flow

    Resources:

    Connect With David Lenok:

    Connect With Sean Weissbart:

    About Our Guest:

    As one of the most regarded millennial estate planners in the country, Sean plays an integral role in the lives of his clients, working together to create legacies that are tax efficient and responsive to the unique needs of each family.

    On Sean’s practice and style, Chambers USA quotes a client saying that “Sean Weissbart is a very creative estate tax lawyer, and he’s always looking to provide a fuller package than just documents. He cares quite a bit about his bedside manner, and it shows.” Another states, “There are three things that stand out about Sean. First is his ability to accommodate clients, second is his passion for the work he does and third is his empathy.”

    Clients turn to Sean to handle all aspects of estate planning, the administration of trusts and estates, and the representation of beneficiaries and fiduciaries in contested matters in Surrogate’s Court. Sean’s extensive experience includes advising international families on the impact of U.S. tax laws on their wealth. In international estate matters, Sean assists non-citizens with domestic assets navigate the complicated rules surrounding the tax-efficient transfer of their wealth and counsels U.S. citizens facing income tax issues related to their beneficial interest in foreign trusts.  

    Sean also represents clients on matrimonial matters, including the negotiation of prenuptial and postnuptial agreements and trust modifications following divorce.

    In addition to his law practice, Sean serves as an adjunct professor of law at New York University School of Law, where he teaches Income Taxation of Trusts and Estates, International Estate Planning, and Tax Aspects of Charitable Giving. He is an author of the law school textbook The Income Taxation of Trusts and Estates, a fellow of The American College of Trust and Estate Counsel, and a regular speaker at the nation’s most prestigious tax conferences. He gives back to the community through many philanthropic endeavors including his service on the board of the Ment’or BKB Foundation and as event chair of the Trusts and Estates Committee of the UJA Federation of New York, having raised millions of dollars to assist those in need.

    28 January 2026, 4:20 pm
  • 30 minutes 21 seconds
    Celebrity Estates: Philanthropy, Legacy and Family Wealth with Philip Richter

    Legacy is often shaped less by what is given and more by how values are shared across generations.

    In this episode of Celebrity Estates, wealth manager Philip Richter joins the show to explore philanthropy as a core part of estate planning and family decision-making. The conversation examines The Giving Pledge and how charitable intent, when left informal or unspoken, can lead to confusion, missed opportunities and misalignment among heirs.

    Philip explains why separating legacy from inheritance helps families focus on purpose rather than dollar amounts. He also shares how donor-advised funds, private foundations and charitable trusts can bring structure to giving while encouraging communication and shared responsibility.

    Join Senior Editor David Lenok and Philip Richter, president and partner at Hollow Brook Wealth Management, as they break down the estate planning lessons behind philanthropy, generational education and building a legacy that extends beyond assets.

    Philip discusses:

    • How philanthropy can strengthen family communication while aligning values across generations through shared giving plans
    • Why separating legacy from inheritance helps families focus on purpose, not just asset transfer
    • Common structures for charitable giving, including donor-advised funds, private foundations, and charitable trusts
    • The role advisors play in moderating sensitive family discussions around wealth, values, and responsibility
    • Why early education and transparency prepare heirs to steward both capital and charitable intentions

    Resources:

    Connect With David Lenok:

    Connect With Philip Richter:

    About Our Guest:

    Philip Richter is the President and Partner of Hollow Brook Wealth Management where he oversees firm-wide client relations, marketing and business development, and sits on the investment committee. Philip is involved with asset allocation, manager selection, and equity research. Philip previously served on the board of directors of WidePoint Corporation (NYSE: WYY). Currently, Philip sits on the board of the United States Equestrian Team Foundation, the United States Equestrian Federation, Revs Institute, and the Pray Family Foundation. Philip is the Chairman of the Lake Placid Horse Show, and the Treasurer of the Hampton Classic Horse Show. Philip received a BA from Boston College and an MBA from the Stern School of Business at New York University. Philip is a vintage car enthusiast who maintains a collection of modern classics and pre-war motorcycles. He participates in international car shows, hosts the Turtle Invitational (a biennial car show in Bedford, NY), and is a regular contributor to many equine and collector car publications. Philip also competes in equestrian show jumping in the high amateur-owner division.

    22 December 2025, 11:00 am
  • 36 minutes 16 seconds
    Celebrity Estates: When Inheritance Hurts More Than It Helps with Don D. Ford III

    Money passed down with good intentions can still create conflict, confusion and long-lasting family tension.

    In this episode of Celebrity Estates, estate planning attorney Don D. Ford III joins the show to examine why more high-net-worth families are choosing to limit inheritances, not out of neglect, but out of concern for the long-term health of their family relationships. The discussion centers on how silence, assumptions and sudden wealth transfers can trigger conflict.

    Don shares how unequal planning, lack of preparation and delayed conversations frequently lead to disputes between siblings. He also shares real examples showing how family meetings, philanthropy and thoughtful trust structures can reduce confusion and set clearer expectations.

    Join Senior Editor David Lenok and Don Ford, managing partner at Ford + Bergner, as they unpack the estate planning lessons behind inheritance decisions that are meant to protect families, not divide them.

    Key takeaways:

    • Why sudden wealth transfers often strain sibling relationships, and how early conversations can reduce resentment
    • How family meetings help define shared values, expectations and long-term intentions around money
    • The difference between equal treatment and fair treatment among children with different abilities
    • Ways philanthropy can unite heirs and create shared purpose beyond personal inheritance
    • Why silence around estate plans often leads to confusion, conflict and costly disputes

    Resources:

    Connect With David Lenok:

    Connect With Don Ford:

    About Our Guest:

    Don D. Ford is the managing partner of Ford + Bergner, an estate planning and probate law firm with offices in Houston, Dallas, and Austin. His practice focuses on guiding families through complex estate planning, probate administration, and guardianship matters, particularly for high-net-worth households. Board-certified in estate planning and probate law by the Texas Board of Legal Specialization, Don is also trained in mediation and has served on the state guardianship certification board, where he helped shape policy and oversight for professional guardians.

    16 December 2025, 3:20 pm
  • 33 minutes 16 seconds
    Celebrity Estates: The Estate Lessons Behind Jean-Michel Basquiat with Doug Woodham

    Stories about legacy often reveal more than the moments that made someone known. 

    In this episode of Celebrity Estates, author and advisor Doug Woodham joins the show to explore how Jean-Michel Basquiat’s unexpected passing set off a chain of estate challenges tied to illiquid assets, sudden value changes and family decisions.

    Doug explains how the absence of a will, a large collection of artwork and a fast-rising market created valuation hurdles, tax pressure and liquidity strain. He also shares how disputes, incomplete records and shifting asset values shaped the long-term direction of the estate.

    Join Senior Editor David Lenok and Doug Woodham, managing partner at Art Fiduciary Advisors, as they break down the estate lessons behind one of the most unusual art legacies in recent history.

    Key takeaways include:

    • Illiquid assets, volatile markets and rapid posthumous value growth
    • Blockage discounts and how large holdings of one artist complicate valuations
    • Family dynamics, estranged parents and unexpected inheritance patterns
    • IRS disputes, liquidity strain and complex tax negotiations
    • How Basquiat’s sisters eventually managed a growing licensing business

    Resources:

    Connect With David Lenok:

    Connect With Doug Woodham:

    About Our Guest:

    Doug Woodham is Managing Partner of Art Fiduciary Advisors and the former President of the Americas for Christie’s, the international auction house. Earlier in his career, he was a partner at McKinsey & Company, advising asset management and wealth management firms across the U.S., Europe, and Asia. He holds a Ph.D. in economics from the University of Michigan and is the author of Jean-Michel Basquiat: The Making of an Icon (Thames & Hudson; 2025) and Art Collecting Today: Market Insights for Everyone Passionate About Art (Allworth Press, 2017).

    26 November 2025, 11:00 am
  • 29 minutes 45 seconds
    Celebrity Estates: The Lessons Behind Gene Hackman’s Estate with Victoria Gray

    On this episode of the Celebrity Estates podcast, Victoria Gray, founder and principal of Insight Art & Collectibles Advisory, once again joins WealthManagement.com Senior Editor David Lenok to examine the tragic and complex estate of actor Gene Hackman, a case where timing, trust gaps and estranged heirs collided.

    From an $80 million fortune and a decades-old will to simultaneous death rules and charitable trusts, Victoria unpacks how not regularly updating the estate plan shaped the outcome. Drawing on her years advising fiduciaries and families, she explains why ongoing estate reviews, succession planning and clear documentation are critical to preserving both wealth and intent.

    Key Takeaways:

    • The impact of failing to update an estate plan for nearly two decades
    • How simultaneous death laws can complicate estate distribution
    • The role of trusts in preventing intestacy and potential family disputes
    • The importance of successor trustees and contingency planning
    • How art, memorabilia and even Oscars factor into estate valuations.

    Resources:

    Connect With David Lenok:

    Connect With Victoria Gray:

    About Our Guest:

    Victoria Gray is one of the art market’s most trusted and accomplished insiders, bringing more than two decades of high-stakes experience to the sale and stewardship of the world’s most coveted tangible assets. As the Founder of Insight Art & Collectibles Advisory, she serves a global clientele navigating the complexities of selling fine art, jewelry, watches, wine, classic cars, and other collectible property, ensuring every transaction is executed flawlessly, strategically, and to maximum advantage.

    Before launching Insight, Victoria spent over 20 years at Bonhams, one of the world’s oldest and most prestigious auction houses, rising to Deputy Chairman of North America, while starting her career at Sotheby’s, a leading global auction house.

    During her tenure, she served as Senior Vice President, Managing Director of the Valuations, Trusts & Estates Department, and Head of Office for Bonhams San Francisco. She also built and led Bonhams’ Trusts & Estates presence in New York, forging deep relationships with elite trust & estate attorneys, fiduciaries, wealth managers, and family offices nationwide.

    10 November 2025, 11:00 am
  • 22 minutes 45 seconds
    Celebrity Estates: The John Amos Estate Dispute with Michael Napoleone

    Family drama doesn’t end when the spotlight fades.

    On this episode of the Celebrity Estates podcast, litigator Michael Napoleone joins Wealthmanagement.com Senior Editor David Lenok to unpack the bitter dispute over actor John Amos’s estate, and what it reveals about aging, trust and family dynamics.

    From allegations of elder abuse and undue influence to sibling rivalries turned legal battles, Michael shares what really happens when communication and transparency break down. Drawing on years in the courtroom, he explains why longer lifespans, cognitive decline and blended families are fueling a rise in inheritance disputes — and how proactive planning can protect both wealth and relationships.

    Key Takeaways:

    • Why family disputes over caregiving and inheritance are rising as people live longer and cognitive decline increases
    • How isolation, blended families and uneven caregiving fuel mistrust and legal challenges
    • The difference between exploitation claims (while alive) and undue influence claims (after death)
    • The crucial role of fiduciaries and when a neutral party may prevent emotional and financial fallout
    • Why clear communication about estate intentions can prevent surprise, resentment, and years of litigation

    Resources:

    Connect With David Lenok:

    Connect With Michael Napoleone:

    About Our Guest:

    Michael Napoleone is a seasoned litigator with a proven track record of success representing businesses, individuals, and fiduciaries in complex, high-stakes disputes. He has litigated a wide array of matters, including theft of trade secrets, corporate shareholder disputes, contested wills and trusts, claims of fiduciary misconduct, land use conflicts, and high-value real estate litigation. His extensive courtroom experience spans jury trials, bench trials, appeals, and alternative dispute resolution forums such as arbitration and mediation.

    Known for his strategic approach and persuasive advocacy, Michael is regularly called upon to handle cases where the outcome is critical and the legal issues are complex. His clients rely on him not only for his legal acumen but also for his ability to navigate sensitive, high-conflict situations with clarity and confidence.

    In addition to his legal practice, Michael has held many leadership roles within the legal profession and local government. He is a past president of the Palm Beach County Bar Association and served on the Executive Board of the Palm Beach County Early Learning Coalition. He currently serves as the elected Mayor of the Village of Wellington, Second Vice President of the Palm Beach County League of Cities, and on the Executive Board of the Palm Beach County Transportation Planning Agency – positions that reflect his dedication to public service and his deep understanding of governmental and regulatory systems.

    Michael’s dual background as a skilled courtroom advocate and respected civic leader makes him a trusted advisor in both legal and policy arenas.

    27 October 2025, 11:00 am
  • 34 minutes 8 seconds
    Celebrity Estates: Updating Estate Plans Through Life’s Milestones

    Life changes, and your estate plan should change with it. Attorney Matthew Erskine joins the Celebrity Estates podcast to explain why estate planning is never a “set it and forget it” process, but a lifelong practice that evolves alongside major milestones.

    Matthew walks through key life events from marriage and divorce to relocation and retirement and shares how each can reshape a client’s estate strategy. Drawing from years of experience, he highlights how small updates, communication and awareness of changes in the law can prevent major family disputes.

    Join Senior Editor David Lenok and Matthew Erskine, ower of The Erksine Company, as they discuss how to keep estate plans living, relevant and aligned with every stage of life.

    David and Matthew discuss:

    • Why every major life event, from marriage to relocation, should trigger a review of your estate plan
    • The importance of communication between family members to avoid future conflicts
    • How to handle estate planning for beneficiaries facing personal challenges
    • The impact of tax and law changes on existing estate documents
    • Why advisors should treat estate plans as “living documents” and revisit them annually

    Resources:

    Connect With David Lenok:

    Connect With Matthew Erskine:

    About Our Guest:

    Matthew F. Erskine is an approachable, empathic estate and succession planning attorney who creatively and holistically solves families’ unique asset and estate needs. He is the fourth generation of lawyers known for integrity and personal service. Matt concentrates on providing legal and fiduciary services for families with basic estates as well as real estate, unique assets, or a family business. Unlike most trust and estate attorneys, Matt’s focus is on ensuring financial security while preserving the ownership of unique but often illiquid assets for the client and family.

    20 October 2025, 11:00 am
  • 24 minutes 17 seconds
    Celebrity Estates: Giorgio Armani’s $12B Legacy and Succession Plan

    Giorgio Armani left behind more than fashion when he passed away at 91. His $12 billion empire, absence of direct heirs and a carefully crafted foundation raise essential estate planning lessons that extend beyond celebrity headlines.

    Kevin Ghassomian, partner at Venable LLP, explains how Armani separated wealth from control, empowered trusted collaborators, and institutionalized his brand to ensure continuity. He emphasizes the importance of early planning, communication and mission-driven structures in preserving wealth and vision.

    Join WealthManagement.com Senior Editor David Lenok and Kevin for a compelling discussion on the lasting lessons Armani’s estate provides for families, advisors and business owners alike.

    Key takeaways:

    • Armani’s early planning, which began in 2016, allowed for a structured succession strategy
    • The separation of personal assets from business assets to protect brand identity
    • The creation of a foundation to act as the steward of Armani’s legacy, ensuring mission-driven continuity
    • The benefits and challenges of planning without a spouse or children, highlighting freedom vs. overwhelm
    • Practical lessons business owners of all sizes can apply, such as buy-sell agreements, trusts and meaningful communication.

    Resources:

    Connect With David Lenok:

    Connect With Kevin Ghassomian:

    About Our Guest:

    Kevin Ghassomian focuses his practice on the personal legal needs of business owners, corporate executives, high-net-worth individuals, and their families. Kevin’s representation covers all aspects of domestic and international estate planning, with an emphasis on tax minimization, asset protection, business succession, and philanthropy. Kevin also counsels individual and corporate fiduciaries on the administration of trusts and estates, including the preparation of gift and estate tax returns and defense of positions taken on those returns.

    Kevin previously worked in the New York City headquarters of a global investment company, where he counseled a multinational client base on complex wealth management matters, including foreign and domestic trust planning and related asset allocation strategies. Kevin leverages this background to collaborate with tax, investment, and insurance advisors, ensuring that their work is effectively integrated into the planning process.

    In addition to his law practice, Kevin is a frequent speaker, a published author, and a former professor of law, concentrating his scholarship on estate planning, taxation, and various wealth management topics. He also devotes time to numerous civic and charitable causes, maintaining leadership positions on several nonprofit boards.

    29 September 2025, 2:02 pm
  • 35 minutes 10 seconds
    Celebrity Estates: Legacy Lessons from Ozzy Osbourne

    Ozzy Osbourne left behind more than music when he passed away at 76. His $250 million fortune, blended family and valuable music royalties raise pressing estate planning questions that extend far beyond celebrity headlines.

    Tasha Dickinson, partner at Day Pitney LLP, shares how advisors can address family conflict, use independent fiduciaries and manage complex assets like royalties. She highlights the crucial role of communication and expectation-setting in preventing disputes.

    Join WealthManagement.com Senior Editor David Lenok and Tasha for a compelling conversation on the lessons Ozzy’s estate offers for families and advisors alike.

    Tasha discusses:

    • The unique estate challenges faced by blended families and strategies to reduce conflict
    • The importance of appointing an independent fiduciary rather than family members to administer estates
    • How communication and expectation-setting can prevent litigation
    • The complications of managing royalties, intellectual property and other nontraditional assets
    • Why advisors should work as a unified team with attorneys and CPAs early in the planning process
    • And more!

    Resources:

    Connect With David Lenok:

    Connect With Tasha Dickinson:

    About Our Guest:

    Tasha Dickinson, a Florida Bar Board Certified Wills, Trusts and Estates Lawyer, exclusively represents individuals and families in sophisticated estate planning and estate/trust administration. She has extensive experience with complex wealth preservation strategies, business succession planning, and charitable planning. She represents fiduciaries in complicated estate and trust administration matters. Tasha has developed a niche working with family offices and has written and lectured extensively on residency planning.

    22 September 2025, 11:00 am
  • 27 minutes 16 seconds
    Celebrity Estates: Blended Families, Disclaimers, and Hulk Hogan’s $25 Million Estate

    When wrestling legend Hulk Hogan passed away, he left behind more than a fortune; he left a tangled family web.

    In this episode, David Lenok talks with Lawrence D. Mandelker, Partner at Venable LLP, to discuss the estate challenges surrounding Hogan’s $25 million legacy. 

    Together, they explore how blended families, strained relationships, and renounced inheritances highlight the planning pitfalls that advisors see every day. From fairness vs. equality to the tools that can prevent disputes, this episode offers lessons advisors can apply directly with their clients.

    Key Points:

    • Hulk Hogan’s life, fortune, controversies, and blended family structure
    • Estate planning challenges with multiple marriages, stepchildren, and strained relationships
    • How advisors can help clients balance fairness vs. equality among heirs
    • Discusses tools like trusts, disclaimers, and no-contest clauses to prevent family disputes
    • Why proactive conversations and lifetime gifts can reduce surprises and conflicts later
    • And more!

    Resources:

    Connect With David Lenok:

    Connect With Lawrence D. Mandelker:

    About Our Guest:

    Larry Mandelker helps high-net-worth individuals with estate planning by counseling on mutigenerational transfers of assets and business succession planning. Through the use of wills, trusts, and other estate planning instruments, Larry works with his clients to creatively design estate plans that address their unique needs and plan for future contingencies, while also focusing on asset preservation, premarital planning, and estate, gift, and income tax minimization goals. His clients include individuals in many industries, including corporate executives and founders, owners of closely held businesses, real estate owners and developers, financial principals, technopreneurs, entertainers, athletes, and publishers.

    27 August 2025, 11:00 am
  • 34 minutes 35 seconds
    Celebrity Estates: George Foreman and Legacy Planning

    In this episode of Celebrity Estates, host David Lenok welcomes Ian Freeman, founder of The Freeman Group and a Northwestern Mutual Wealth Management Advisor, for a conversation inspired by the estate of legendary boxer and entrepreneur George Foreman. 

    From naming all five of his sons “George Edward Foreman” to building a $300 million fortune, David and Ian explore how identity, family dynamics and unspoken expectations shape legacy. Ian offers practical insight into the emotional side of wealth transfer and how advisors can foster deeper, more meaningful planning conversations.

    Ian discusses:

    • George Foreman’s estate strategy and the symbolic power of naming all his sons after himself
    • The emotional and psychological layers of wealth transfer, especially in multi-generational families
    • The importance of flexibility and open dialogue in estate and legacy planning
    • Common communication gaps and how silence can fracture family trust
    • How philanthropic goals can engage future generations and reflect authentic values

    Resources:

    Connect With David Lenok:

    Connect With Ian Freeman:

    About Our Guest:

    Ian Freeman is a nationally and internationally recognized financial representative with a career rooted in purpose, resilience, and service. A graduate of Wesleyan University, where he studied government, history, economics, and philosophy, Ian began his professional journey in banking and investment banking before launching his insurance career in 1987, with just a $5,000 loan, heavy debt, and a leap of faith. Since then, he has helped enrich the lives of more than 4,500 individuals, families, and businesses by writing over $2 billion in death benefits.

    Ian ranks among the top 40 in career production at Northwestern Mutual and is one of only two representatives in the company’s history to qualify for both the Northwestern Mutual Forum and Lives Leader Summit every single year since their inception. A Life Member of the Million Dollar Round Table and past president of the Northwestern Mutual Financial Representatives Association, Ian has served on numerous committees and continues to mentor more than 1,000 financial professionals, with a longstanding commitment to multicultural engagement.

    Holding CLU®, ChFC®, CASL®, and AEP® designations, Ian is known for blending deep industry knowledge with authentic client relationships. His practice was honored in the 2005 Northwestern Mutual Annual Report, a recognition he attributes not just to accomplishments, but to character. A passionate speaker and educator, Ian travels the country sharing insights on insurance fundamentals and the true impact of financial guidance.

    Outside of work, Ian enjoys golfing, reading, playing guitar, staying active, and spending time with his beloved Golden Retrievers. For Ian, being a traditional representative isn’t about doing things the old way; it’s about doing them the right way, with heart.

    11 August 2025, 2:56 pm
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