After Jack Anderson died in 2015, an unexpected bill arrived. The state of Connecticut said his estate owed $13.2 million in estate and gift taxes.
The executor of Anderson’s estate, a longtime family confidant named Les Daniels, disagreed. How could the estate be subject to these Connecticut taxes when his late friend’s official home was a 9,700-square-foot oceanfront mansion in Vero Beach, Fla.? Daniels saw it as an unfair tax grab.
The decadelong legal battle is just now reaching a crescendo. In June, the high court made it easier for the Anderson estate to prove its case and ordered a new trial.
For the growing ranks of wealthy Americans, which state they call home is more contentious than ever. States are getting more aggressive in going after people they think owe them taxes. New York City recently passed a pied-à-terre tax on nonresidents, and California has proposed a wealth tax on billionaire residents.
It is all increasingly complicated when people can work anywhere and have multiple homes. The fights between states and the wealthy are playing out in an increasing number of residency audits.
That is the issue with the $108 million Anderson estate. Anderson ran a hospital-management company and was an early leader in HMOs in the U.S. He and his wife split their time among their homes. At the time of his death at age 90, he had the oceanfront property in Florida, the condos in Greenwich, and a mountaintop home in Arizona, with luxury cars at each.
The Connecticut Supreme Court, it its June ruling, set a lower standard of evidence for taxpayers to prove they are not domiciled in the state, that standard is a preponderance of the evidence. Applying that new standard could wipe away the tax bill in the Anderson case. And it could pave the way for other families to more easily win income and estate tax audits in Connecticut and elsewhere.
While the federal estate tax hits only the wealthiest Americans, the thresholds for state estate and inheritance taxes are generally much lower and can catch even middle-class families by surprise. When Anderson died more than a decade ago, the Connecticut estate tax kicked in for estates valued above $2 million. It now hits far fewer taxpayers as the threshold matches the federal exemption amount, which is $15 million for 2026 and is indexed for inflation.
Starting in 2017, the state tax auditor asked Anderson’s estate for many documents to figure out which state he intended as home. The presumption is Anderson was a Connecticut domiciliary unless his estate can prove otherwise.
The eventual trial in the superior court tax division in 2024 lasted four days, with 10 witnesses and 200 exhibits. The estate tax returns, federal and state, totaled some 4,000 pages.
The trial court judge homed in on one factor: Anderson typically spent 5½ months a year from May to mid-October in Greenwich, and 3½ months from November through mid-February in Florida. He spent three months from mid-February through early May in Arizona.
The judge concluded that “ultimately, the most persuasive evidence demonstrating Anderson’s domicile is where he chose to spend his most valuable and limited resource: his time.”
For more information see Ashlea Ebeling “Was His Home Connecticut or Florida? The Difference Is a $13 Million Tax Bill” The Wall Street Journal, August 7, 2026.