assets time to appreciate outside the estate.
The strength of the Jackie O. CLAT is in its balance of objectives. It fulfills the grantor’ s charitable goals, secures a tax deduction, and stages generational transfers over time. It also supports the grantor’ s public reputation, demonstrating their civic contribution while discreetly preserving their family’ s capital.
Since the creation of the Onassis vehicle, CLATs have evolved. Both lifetime and testamentary versions can feature flexible terms, income-tax strategies, and multigenerational planning. And when families pair a CLAT with a charitable remainder trust, the combination can provide them with income during the charitable term while they retain the tax advantages. Together, these vehicles create a layered system that offers the family near-term liquidity and longterm leverage( as well as demonstrating the entire family’ s charitable intentions).
The Jackie O. CLAT endures not for aggressiveness but for its elegance, showing how well-structured philanthropy can deliver many attractive benefits in one integrated vehicle.
The Newman Foundation
Paul Newman’ s legacy extends beyond movie screens and into a philanthropic model that reimagined how private enterprise can serve the public good. His food company, Newman’ s Own, was structured from the outset to direct all its profits to charity. The ownership design— a private foundation holding 100 % of a for-profit business— became a landmark example of how charitable impact can be aligned with thoughtful tax efficiency.
Rather than sell the business or pass it to heirs, Newman ensured the company would be owned by his Newman’ s Own Foundation, a 501( c)( 3) nonprofit. The profits flowed as dividends to the foundation, which then distributed them to charitable causes. The family’ s involvement was advisory rather than economic. This preserved the brand, eliminated estate taxes, and kept mission, not money, at the center of the estate.
Ordinarily, private foundations may not own more than 20 % of a for-profit company. In 2018, however, Congress passed a narrow provision known as the“ Newman’ s Own exception,” allowing 100 % ownership if strict requirements are met: the profits must go to charity; no form of compensation( direct or indirect) may be paid to an insider( a substantial contributor to the foundation); and the for-profit business must be operated independently of the foundation. This legislation formalized what Newman had pioneered and opened a path for other families to follow.
Strategically, the model avoids estate taxes while ensuring the organization has a charitable mission.
Symbolically, it transformed a private business into a philanthropic engine. For families wanting to anchor legacy and purpose without liquidation, the Newman Foundation model offers a compelling way forward.
Of course, the approach demands rigorous attention to governance, compliance and mission alignment. But when it’ s executed well, it reframes wealth as a tool for public benefit. Newman did not simply give away his fortune; he built a business enterprise with giving woven into it.
The Lender Single Family Office
The Lender family, of Lender’ s Bagels fame, made estate planning history not through their operating business but in the way they managed their wealth after its sale. Their single-family office showed how one could preserve the deductibility of investment management expenses after the 2017 Tax Cuts and Jobs Act eliminated miscellaneous itemized deductions for individuals.
Before the 2017 law, advisory fees could be deducted as miscellaneous itemized deductions subject to a floor of 2 % adjusted gross income. But with the enactment of the law, those deductions disappeared for most individuals, making the cost fully non-deductible. The Lender family, however, had structured their single-family office to qualify as a stand-alone business under Section 162 of the Internal Revenue Code, which allowed it to deduct investment-related expenses as ordinary business costs.
The single-family office operated as a limited liability company. It employed professionals and served multiple family trusts under formal agreements. In Lender Management v. Commissioner, the U. S. Tax Court confirmed that its functions met the definition of a trade or business.
This ruling clarified a longstanding gray area. Under the right conditions, managing family wealth can be treated as a business activity for tax purposes. For families with millions in annual advisory expenses, the implications were significant.
Because the One Big Beautiful Bill Act of 2025 did not restore the deductibility of investment fees for individuals or trusts, the Lender approach remains both viable and valuable. It is not a loophole but a blueprint for turning a cost center into a professional enterprise with legitimate tax advantages.
Conclusion
The strategies associated with these famous icons are not notable for their aggressiveness but for their intentionality. Each was built within the law— yet executed with vision. They did more than reduce taxes; they clarified the families’ purpose, reinforced their values, and created systems built to last.
The Walton GRAT demonstrates the power of repetition and leverage. The Jackie O. CLAT turns time and charity into a multidimensional planning tool. The Newman Foundation shows how business ownership can be harnessed for mission. The Lender single-family office proves that a governance and structure can deliver tax efficiency even when statutory avenues narrow.
Modern ultra-wealthy families may not replicate these models exactly, nor should they. The value lies in what these examples teach: Strategy starts with clarity, capital benefits from direction, and the best tax planning is as much about design as it is about compliance.
The next great strategy will do the same, not just by helping families avoid tax, but by creating structures that align capital with purpose and purpose with permanence.
JEFF GETTY is chief tax strategist at Callan Family Office, where he oversees firm-wide research and strategy on complex income, transfer and international tax issues for ultra-high-net-worth families, closely held businesses and private investment firms. Callan Family Office does not provide tax or legal advice.
SEPTEMBER 2025 | FINANCIAL ADVISOR MAGAZINE | 55