Lessons on Estate Planning From the Rich and Famous

Famous people like Jacqueline Kennedy Onassis, Paul Newman and Sam Walton (founder of Walmart) have created more than just famous businesses, legends, or movies. Their estate planning innovations are the subject of a recent article, “How Iconic Estate Plans Teach The Affluent About Wealth Preservation” from Financial Advisor.

The examples illustrate the creation of now commonly used legal strategies, as well as what can happen when the goal is to take a long-term, values-driven approach to creating a legacy with stewardship in mind. Even if you don’t have a $50 million estate, there are still lessons to be learned from what their estate plans accomplished.

The Walton GRAT refers to a Grantor Retained Annuity Trust, a type of trust created with a distinct approach to intergenerational wealth transfer. The Walton family used rolling GRATs to shift billions of dollars of appreciation out of their estates with little or no gift taxes. This use of GRATS in a highly systematic method is scaled to their vast wealth and synchronized with a capital plan.

GRATs are used to let a grantor contribute appreciating assets into a trust while retaining an annuity for a fixed term. If the assets outperform a rate set by the IRS (Section 7520), the excess appreciation passes to heirs tax-free. The Walton difference was the use of short-term, rolling GRATs on a large scale, capturing small increments of growth.

The Jackie O. Charitable Lead Annuity Trust (CLAT) brought the use of testamentary Charitable Lead Annuity Trusts to the forefront of estate planning. They are used to pay a fixed annuity to a charity for a set term, after which the remaining assets are passed to the beneficiaries. CLATs are not new. However, Jackie’s CLAT balanced charitable giving, tax deductions and the transfer of generational wealth privately and over a long period of time. It was designed to be effective and discreet, aligning with her low-key profile, and enabled generous civic contributions.

The Newman Foundation reimagined how private enterprises can serve the public good. Paul Newman founded the company Newman’s Own, structured from the start to direct all profits to charity. Rather than sell the business or pass it to heirs, Newman’s Own is owned by the Newman’s Own Foundation, a registered 501(c)(b) nonprofit. Profits flow to the foundation, which then makes grants to charities. The brand is preserved, there are no estate taxes and the mission, not the profits, is at the center of the foundation. Achieving this structure requires rigorous attention to governance, compliance and mission alignment. However, the legacy and impact continue to be significant.

Another well-known food company is Lender’s Bagels. They carved out new territory in estate planning by managing the Lender family’s wealth after the sale of the business. They established a Single Family Office (SFO) and took advantage of changes to the tax law following the 2017 Tax Cuts and Jobs Act (TCJA), which eliminated miscellaneous itemized deductions for individuals.

Before TCJA, advisory fees were deductible as miscellaneous itemized deductions subject to a 2% AGI floor. After TCJA, the deductions disappeared for most people. However, the Lenders structured their SFO to qualify as a standalone business using Section 162, and as a result, they were able to deduct investment-related expenses as business costs.

A dispute over the structure was taken to tax court. However, the tax court’s decision was that the functions of the Lender SFO indeed met the definition of a trade or business.

These kinds of strategies are recognized not just for their aggressive nature but for their intentionality. Each was created working within the restrictions and regulations of estate planning and tax law. They demonstrate how strategic estate planning can reinforce the family’s values and remain effective across multiple generations. In essence, they illustrate what estate planning can do for the present and the future of a family.

Famous estates show that thoughtful planning can do more than preserve wealth—it can protect family values, support charitable causes, and create a lasting legacy. Whether your estate is modest or substantial, working with an estate planning attorney ensures your plan aligns with your priorities and safeguards your loved ones. At The Werner Law Firm, our experienced estate planning team helps families craft estate plans that provide clarity, protection, and peace of mind.

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Reference: Financial Advisor (Aug. 12, 2025) “How Iconic Estate Plans Teach The Affluent About Wealth Preservation”