A $13.2 Million Tax Fight Over a Dead Billionaire's 'True Home'

When Jack Anderson died in 2015 at age 90, leaving behind a $108 million estate, Connecticut sent his executor a $13.2 million bill for estate and gift taxes — even though Anderson had a Florida driver's license, voted in Florida, and listed his 9,700-square-foot oceanfront Vero Beach mansion as his address in his will. The ensuing legal battle, now more than a decade old, has reached the Connecticut Supreme Court and is reshaping how domicile disputes are fought across the country.

Anderson was a pioneer in hospital management and early HMO development. He and his wife Rose-Marie owned multiple luxury properties simultaneously: three condominiums totaling 9,000 square feet in Greenwich, Connecticut; the oceanfront Vero Beach home he built to custom specifications with a private boardwalk and hand-painted dining room murals; and a mountaintop retreat in Arizona, with a fleet of luxury cars — including Jaguars, Bentleys, and a Mercedes — registered at each location. Connecticut argued he was domiciled there because he spent roughly 5.5 months a year in Greenwich, registered his nurses for Connecticut tax withholding, and held memberships at Greenwich Country Club and the Clove Valley Rod & Gun Club. The trial court agreed, finding time spent the single most persuasive factor.

The estate pushed back hard. Anderson's autobiography consistently described Texas and then Florida as home. His will, Florida voter registration, gun registration, and driver's license all pointed south. The estate also argued a stark qualitative gap between the properties: the Florida home was built to Anderson's personal specifications as a primary residence, while the Connecticut condos were purchased incrementally over decades. A four-day 2024 trial produced 10 witnesses, 200 exhibits, and a federal and state tax return totaling 4,000 pages — and still went against the estate.

The Connecticut Supreme Court intervened in June, lowering the evidentiary standard the estate must meet. Previously, the estate had to prove by "clear and convincing evidence" that Connecticut wasn't Anderson's domicile — a high bar. Now it only needs to show it by a "preponderance of the evidence," the more common civil standard. That shift orders a new lower-court trial and could wipe out the entire $13.2 million tax bill. It also sets a precedent that could make it easier for other wealthy families to win residency audits across Connecticut and potentially other states.

The stakes extend well beyond one family's dispute. Sixteen states plus D.C. still impose estate or inheritance taxes, and states are increasingly aggressive in chasing wealthy movers. New York City recently passed a pied-à-terre tax on nonresidents; California has floated a billionaire wealth tax. Connecticut itself collected an estimated $261 million in estate and gift taxes last fiscal year. As remote work and multi-home lifestyles make domicile ever harder to pin down, tax lawyers say residency audits are multiplying fast — and the Anderson case will be closely watched as a potential roadmap for how to win them.