When the Music Stops: Lessons from Three Estates Gone Wrong
Even celebrities and TV icons can fall victim to the consequences of poor estate planning. These three stories underscore the importance of thoughtful estate and tax planning.
Prince: The Artist Who Left No Will
Age: 57
Death: April 21, 2016; Minnesota; accidental overdose of fentanyl
When Prince died in 2016, the world mourned, and his estate fell into a purple haze of legal disputes. Without a will, the $156 million fortune remained tangled in court for six years, and even in 2024, lawsuits over trust violations persisted. His six half-siblings, two of whom died during the litigation, were declared heirs. Three heirs sold their interest to a company named Primary Wave, now the single largest shareholder (although not majority shareholder) in the royalties, proceeds from name and likeness, and other properties of Prince, further complicating the lawsuits.
Lesson: Without a clear will and estate planning, legal battles can take center stage in even a legend’s legacy. Clarity now can save your heirs from a drawn-out, attorney-fueled encore of “Let’s Go Crazy”.
James Brown: The Godfather of Soul and a 15-Year Legal Battle
Age: 73
Death: December 25, 2006; Georgia; congestive heart failure (fans speculate otherwise)
James Brown’s estate was as dramatic as his performances. His personal life, marked by three marriages and a final relationship to Tomi Rae Hynie, which was annulled after it was revealed she was still married, set the stage for chaos. The Will excluded Hynie, who claimed to be the surviving spouse, and the couple’s son. Fighting is reported to have begun before the memorial service.
On top of marital disputes, at least 12 people claimed to be Brown’s children; DNA tests confirmed some and disproved others. Known for his frugality (he fined band members $5 mid-show for mistakes, “Payback”), Brown reportedly left just $2 million for his grandchildren’s education, costumes to his family, and the bulk of his fortune to scholarships for underprivileged children.
After a grueling 15-year probate battle, incurring tens of millions in legal fees, the estate was settled in 2021, and the heirs sold Brown’s music rights and proceeds from his image and likeness to Primary Wave Music for $90 million.[1]
The Lesson: Even the best intentions need airtight legal documentation to make sure your “I Feel Good” moment lasts beyond your lifetime. Complex families require careful planning.
Tony Soprano (James Gandolfini): Fictional Mob Boss, Real-Life Estate Problems
Age: 51
Death: June 19, 2013, Rome; heart attack
HBO’s Tony Soprano may have been fictional, but James Gandolfini’s estate troubles were very real. Gandolfini signed a will just six months before his sudden death, and either didn’t feel the need to estate plan or hadn’t finished. By leaving only 20% of his $70 million estate to his widow, he infamously triggered an unnecessary $30 million tax bill on the other 80% inherited by his children.
His youngest daughter, Liliana, was less than a year old at the time and won’t access her inheritance until she’s 21. His son, Michael, was 13. Gandolfini split his Italian property between them, but with no immediate cash to cover property taxes and upkeep, keeping it in the family may prove difficult.
Lesson: His story is a reminder that even if you subscribe to “never write down what you can’t say out loud,” you still need a tax-efficient and complete estate plan. Remember that without a trust to protect privacy, probate is public. Additional consideration is required for foreign inherited property. Local laws may override U.S. inheritance laws, and property taxes and upkeep are complicated without liquidity.
The Bottom Line
Whether you’re a rock star, a soul legend, or just the leader of your own small empire, estate planning is about more than who gets what; it’s about protecting your legacy, avoiding costly disputes and taxes, and giving your loved ones peace of mind.