Prince had lawyers. Howard Hughes had an empire’s worth of them. Abraham Lincoln was one. None of them left a will, and their families paid for it through years of litigation, eight-figure legal bills, and headlines nobody would want as a legacy.
These stories make great trivia, but for financial advisors, they are something more useful: proof, in vivid detail, of what happens when planning gets postponed.
Only 24% of American adults have a will, according to Caring.com’s 2025 survey, even as Cerulli projects $124 trillion changing hands through 2048. That gap runs straight through most advisors’ books.
Here are six famous cautionary tales worth keeping in your back pocket for the next client who says they will get to it eventually.
24%
of American adults have a will
$124T
projected to change hands through 2048
6
cautionary tales advisors can share with clients
Estate planning terminology
What does it mean to die intestate?
Dying intestate means dying without a valid will. When that happens, state intestacy laws, rather than the deceased’s wishes, determine who inherits. A probate court oversees the process, and the estate often pays more in taxes, fees, and time than it ever would have spent on a plan.
Prince: a six-year, $156 million question mark
When Prince died in 2016, his sister told a Minnesota probate court that no will could be found. What followed was close to a worst-case scenario.
Roughly 700 people came forward claiming to be heirs. The bank appointed to manage the estate drilled open his vault, and the IRS spent years fighting the estate over its value. The administrator said $82.3 million. The IRS said $163.2 million.
The parties eventually settled at $156.4 million. The estate was not resolved until 2022, six years after Prince’s death, with tens of millions consumed by legal and administrative fees along the way.
Advisor takeaway
Extraordinary wealth cannot compensate for absent instructions. Without a valid plan, even the most sophisticated estate can become a years-long public dispute.
Aretha Franklin: a will in the couch cushions
Aretha Franklin’s family believed she died intestate in 2018. Then, months into probate, relatives found handwritten documents in her home: two in a locked cabinet and one in a spiral notebook under the couch cushions.
Her sons spent years in court arguing over which version controlled. In 2023, a Michigan jury finally ruled that the couch notebook was her valid will.
An estate once estimated at $80 million spent five years in litigation that a properly executed document could have prevented, while the IRS pursued nearly $8 million in back taxes.
Advisor takeaway
Having written wishes is not the same as having a clear, properly executed estate plan. Documents must be valid, current, accessible, and consistent with the client’s intentions.
Pablo Picasso: 45,000 artworks and no instructions
Picasso died in 1973, leaving one of the most valuable estates in history, an inventory of roughly 45,000 works, and no will.
Settling the estate reportedly took six years and $30 million while French courts sorted through claims involving his widow, children, and grandchildren.
France ultimately accepted artwork in lieu of estate taxes, which is how the Musée Picasso in Paris came to exist. It was a beautiful outcome for the public, but a brutal one for a family that spent the better part of a decade navigating the estate.
Advisor takeaway
The more complex the assets, the more important the instructions. Illiquid assets, intellectual property, collectibles, and family ownership structures require deliberate planning.
Howard Hughes: 34 years to close the books
After Howard Hughes died in 1976, some 40 purported wills surfaced. They included the infamous “Mormon Will,” which a Nevada court ruled was a forgery before declaring that Hughes had died intestate.
His roughly $2.5 billion estate was first distributed to 22 cousins in 1983, but the final assets were not paid out until 2010, ultimately reaching roughly a thousand heirs and descendants.
It took 34 years to finish administering the estate of a man who could have settled the central question with one valid, signed document.
Advisor takeaway
Uncertainty invites claims. A clear, authenticated estate plan can reduce the opportunity for fraud, competing documents, and avoidable family conflict.
Chadwick Boseman: not just a problem for the ultra-wealthy
Chadwick Boseman’s story lands differently because the numbers are more relatable. He died in 2020 at age 43 without a will, and his wife had to petition the court to administer his probate estate.
Filings showed about $3.88 million in assets, reduced to roughly $2.3 million after taxes, debts, and fees. The remaining estate was split between his widow and his parents under California intestacy law.
Nearly 40% of the probate estate went to costs. For clients who think estate planning is only for people in Prince’s tax bracket, this is the example that can change minds.
Advisor takeaway
Estate planning is not reserved for the ultra-wealthy. Younger clients and families with more familiar levels of wealth can still face significant costs, delays, and loss of control.
Sonny Bono: no plan, even in Congress
Sonny Bono was a sitting U.S. congressman when he died in a 1998 skiing accident, and he left no will.
His widow had to petition to administer the estate, while Cher filed a claim for unpaid alimony. A man claiming to be Bono’s secret son also pursued a share before withdrawing after the court ordered DNA testing.
Even comparatively modest estates can attract complications when there is no valid document to establish the decedent’s wishes.
Advisor takeaway
Complexity is not determined by estate size alone. Former relationships, disputed heirs, blended families, and unclear wishes can complicate estates at nearly any level of wealth.
The advisor’s takeaway: the famous failures are the easy conversation
Every one of these people had access to some of the best legal advice money could buy. What they lacked was not resources. It was urgency, and someone positioned to create it.
That is the advisor’s seat.
You already know which clients have no documents, outdated documents, or a trust that was never funded. The hard part has always been turning that knowledge into completed plans without sending every client into a weeks-long attorney engagement they may quietly abandon.
The biggest estate planning risk is not always complexity. Often, it is delay.
Financial advisors are uniquely positioned to prevent that delay, but only when estate planning becomes part of the client experience rather than a referral they hope gets followed.
This is the gap Wealth.com was built to close.
Advisors use the platform to empower clients to create attorney-grade wills, revocable trusts, powers of attorney, and health care directives, visualize how assets will actually flow, and use Ester® to surface what existing documents really say.
Estate planning becomes a service advisors can deliver, not a referral they hope gets followed.
Your clients can still write a different ending.
Plenty of clients are currently on track for the same outcome at a smaller scale: state law deciding who inherits, probate determining how long it takes, and fees reducing how much remains.
See how Wealth.com helps advisors turn estate planning from a postponed conversation into a completed plan.
