Disinheritance is often viewed as a clean solution to a painful family problem—but in reality, it can create far more conflict, litigation, and long-term harm than people expect. In this Tuesday Triage episode, Jill Mastroianni unpacks what disinheritance actually means, when it tends to arise (often after emotionally charged family gatherings), and why cutting someone out entirely is frequently the riskiest estate-planning move. Through a realistic scenario involving addiction and sibling dynamics, Jill explains how trusts, professional fiduciaries, and no-contest clauses can offer protection without tearing families apart. This episode is about slowing down, thinking clearly, and making estate-planning decisions that protect all of your children.
Disinheritance is often viewed as a clean solution to a painful family problem—but in reality, it can create far more conflict, litigation, and long-term harm than people expect. In this Tuesday Triage episode, Jill Mastroianni unpacks what disinheritance actually means, when it tends to arise (often after emotionally charged family gatherings), and why cutting someone out entirely is frequently the riskiest estate-planning move. Through a realistic scenario involving addiction and sibling dynamics, Jill explains how trusts, professional fiduciaries, and no-contest clauses can offer protection without tearing families apart. This episode is about slowing down, thinking clearly, and making estate-planning decisions that protect all of your children.
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The Death Readiness Podcast
Episode: 54
Title: Why Disinheritance Can Be the Riskiest Estate Plan
Host: Jill Mastroianni (Solo)
Published: December 30, 2025
Jill Mastroianni (00:00): Disinheritance is often framed as a solution—but it can create far more problems than it solves. In today’s Tuesday Triage episode, I explain what disinheritance actually is, when it might seem justified, and how it can escalate family conflict. Using examples involving addiction and sibling dynamics, we’ll explore practical alternatives, including no-contest clauses and protective trust structures. This episode is about slowing down, thinking clearly, and protecting your family from avoidable harm.
Welcome to the Death Readiness Podcast. This is not your dad’s estate planning podcast. I’m Jill Mastroianni, former estate attorney, current realist, and your guide to wills, trusts, probate and the conversations no one wants to have. If your Google search history includes, “Do I need a trust?” “What exactly is probate?” and “Am I supposed to do something with mom’s Will?” you’re in the right place.
(01:05) Before we get started, I want to share a resource I built for people in the thick of it—juggling kids, parents, and everything in between. The Death Readiness Playbook helps you organize information, understand your options, and make thoughtful decisions before emergencies take over. If the new year feels like the right time to get ahead of this, visit deathreadiness.com/playbook. That’s deathreadiness.com/playbook.
As much as we’re told we’re supposed to have magical holiday experiences, that’s not always how it works—especially once we’re old enough to be the ones responsible for making the magic happen.
When I was in my twenties and living in Manhattan, I subscribed to an email newsletter called Daily Candy. Through it, I scored two free tickets to the opening night of a Steve Carell movie called Dan in Real Life. I met my best friend Lauren there, and we laughed the entire time. The movie was warm and funny and full of family chaos—the kind that still felt charming at that stage of life. At that point, we still believed in holiday magic without reservation.
(02:17) I grew up spending holidays at Big Moose Lake with my parents’ closest friends, Hal and Pam, and their five kids. My family lived on Long Island full-time, but in the early 1990s my parents and their friends bought a couple of run-down buildings on the lake and slowly fixed them up. We spent summers and holidays there, together.
When my sister turned sixteen, on Thanksgiving Day, Hal and Pam’s family painted wooden signs and hung them along the rural road leading to our house. We nearly missed the first one, but my grandmother insisted she’d seen something, so we turned back. The sign read: Happy Birthday, Alyssa. Farther down: Alyssa’s Sweet Sixteen. When she turned twenty-one, also on Thanksgiving, we dressed up and had a karaoke party with both families.
(03:07) One Christmas, Hal and Pam’s youngest child insisted we all go for a walk and then join them for dessert. While we were gone, the rest of Hal and Pam’s family went to our house and stole every dessert we had. When we arrived at their place, all of our desserts were laid out on their table, waiting for us.
We rang in Y2K on our dock, surrounded by snow and sparklers. We went sledding by moonlight. That was the magic of the holidays.
But holidays feel different when you’re the one in charge. When you’re responsible for the Costco desserts and the meal planning and the laundry. When vacations feel less like magic and more like logistics.
As an adult, you start to notice the tension you missed as a kid. You brace yourself for the casually hurtful comment from an in-law—after you’ve already given everything you have to give. You’re tired. You’re overwhelmed. You may be more easily hurt than your parents were—or maybe they were just better at hiding it.
(04:08) And so, as the holiday glow wears off, after long stretches of time with family, you might find yourself thinking: There’s someone in this mix I might need to disinherit.
You may even be rehearsing that part of your Will in your head—what you would say, how it would land, and how that person might react. We might ordinarily think of disinheritance as the last vindictive act of a bitter relative. But, could it also be a valid and reasonable option in some situations?
That’s what we’re going to figure out today.
Maybe your holiday looked magical on Facebook or Instagram, but it might not have felt that way on the inside.
Today’s Tuesday Triage didn’t come from a specific listener question. I was inspired to talk about disinheritance today by a recent LinkedIn post from California estate planning attorney Patricia De Fonte. And I had a strong sense that after long stretches of time with family, a lot of people might be feeling exasperated and wondering what their options actually are.
(05:14) So today, we’re going to talk about disinheritance.
First things first: what does it mean to disinherit someone?
To disinherit someone means to intentionally leave them out of your estate plan, so they do not receive property or money from you when you die—even though they would otherwise reasonably expect to inherit from you.
That last part matters.
Let me give you an example of what disinheritance is not.
You host the holiday dinner this year. Ahead of time, you ask for one thing: no politics or religion for the night.
During dessert, Uncle Bob laughs and says, “I know you said no politics, but—” and keeps going anyway.
You redirect. He circles back. When you finally say, “I asked you not to,” he responds with, “You’re too sensitive.”
Nothing explodes. But the message is clear: your boundary doesn’t count. You’re hurt and you’re disappointed.
(06:17) Are you thinking about disinheriting Uncle Bob?
No.
Why not? Because Uncle Bob isn’t realistically expecting an inheritance from you. You’re married. You have kids. Uncle Bob is thirty years older than you. In the unlikely event that he survives you, your spouse and children, not Uncle Bob, are the natural, expected beneficiaries of your estate.
So as irritating as that behavior is, this isn’t a disinheritance scenario.
Now let’s look at a different example.
Your adult son arrives late to a holiday gathering at your home already visibly intoxicated. He insists he’s “fine,” pours another drink immediately, and disappears into the bathroom several times during the evening.
You quietly pull him aside and say, “I’m worried about you. Please spend the night here tonight.”
(07:13)He snaps back, “Stop treating me like a child. I’ve got it under control.”
An hour later, you realize your car is gone.
Nothing catastrophic happens that night. But your other children are upset. And you lie awake thinking:
If I can’t trust my son with his own health and safety, how can I trust him with money, property, or responsibility after I’m gone?
For many parents, it’s moments like this that disinheritance first enters the picture—not as punishment, but as a decision about protecting assets, preventing harm, and not enabling a pattern that’s already causing damage. Sometimes, coming into a significant sum of money can harm a person if they can’t manage it.
Would your son otherwise expect to inherit from you?
Probably yes, especially if you have other children who will receive an inheritance.
Disinheriting your son in this situation would be an active, intentional choice. You would be deliberately deciding not to leave assets to him at your death.
(08:19) So now we have two questions:
Question #1: Should you disinherit your son? For purposes of this narrative, let’s call him John.
Question #2: If you do want to disinherit John, how should you do it?
Whether you should disinherit John is personal. But it’s also the kind of decision that deserves more nuance than a heat-of-the-moment reaction after a hard holiday.
Let’s stay in the addiction scenario for a minute. For years, alcohol dependency and drug abuse were treated like a character flaw—something shameful, something that could be cured by a change of habits.
Today, we have a more medically grounded understanding: addiction is an illness, and for many people it’s chronic. It can require long-term treatment, relapse prevention, and ongoing support.
And that reality matters when you’re doing estate planning.
(09:18) We saw a devastating, real-world example this month in the deaths of filmmaker Rob Reiner and his wife, Michele. Their adult son, Nick Reiner, has been arrested and charged. The case is ongoing and I’m not here to litigate anyone’s guilt or innocence on a podcast.
What I am saying is that the intersection of family crisis, mental health and substance issues, and safety risk is real—and families can find themselves dealing with it in the most unthinkable ways.
So if you have an adult child like John who struggles with addiction, is disinheritance the right tool?
Because if addiction is an illness, and treatment may be lifelong, treatment will be expensive. Do you want to leave John no safety net at all? Or do you want your other children to be the ones constantly funding emergencies and picking up the pieces on their own dime?
(10:17) If you want to leave a financial safety net, and personally, I think you should, the safer way to do it is through a trust, not a direct inheritance. A trust can be designed to support your child without funding the addiction.
Now, trusts like this can include all kinds of guardrails. That’s a bigger topic than today’s Tuesday Triage, but if you want an episode on what those guardrails can look like, email me at jill@deathreadiness.com and tell me. I’ll do a full breakdown on a future Tuesday Triage episode.
If you create a trust, you need someone to manage it—a trustee. Your first instinct might be to name one of your other children.
In this situation, that’s usually a bad idea.
You’re turning a sibling into a gatekeeper. And if John’s behavior is erratic, or unsafe, you’ve just placed your other child directly between John and the money. Let the sibling be a sibling, not a negotiator or a security system.
(11:23) So who can serve?
I often recommend a professional fiduciary, a person or company that serves as trustee as their profession. Will that cost money? Yes. But the better question is: would you rather pay a professional fee—or risk blowing up the relationship between your children by forcing one of them into an impossible role?
That’s the tradeoff this kind of planning is actually about.
And, as far as naming a professional fiduciary, also known as a professional trustee, don’t just name someone and be done with it. Work with that professional fiduciary when you’re drafting the trust to confirm that they are willing and able to serve and comfortable with their responsibilities as articulated in the trust agreement.
Too many people name someone as trustee without working with the trustee to create the trust agreement. If the situation is too risky or too onerous, the trustee will not serve.
(12:22) Before we talk about trusts further, let’s talk about the alternative, disinheritance. Let’s say you really don’t want to leave John anything, not even one cent. You want to leave everything to your other two kids. How would that make them feel?
Would they feel guilty that you left John out? Would they try to compensate on their own? Would any hope of a decent relationship between John and his siblings be destroyed? Probably.
Would your other children be grateful that you left John out? Maybe. But, you know what, that still wouldn’t be easy for them.
Why? Because John would likely sue. And, even if he’s not successful, he sure could run up a huge legal bill for your estate in defending against his claims.
(13:13) What might John even claim? Well, that you were unduly influenced by your other children. You left John out at the direction of your other children. Maybe John would argue that you were not of sound mind when you made your estate plan.
Couldn’t John sue whether or not you leave him money? For example, what if you leave him money but he’s mad that you left it in trust or he’s mad that you didn’t leave him more.
Well, there’s something called a no contest clause that could help with that.
A no-contest clause is a provision in a will or trust that says, essentially:
If you challenge this document and lose, you also lose what I left you.
It’s meant to discourage lawsuits by raising the stakes.
Instead of asking, “Can I get more?” a beneficiary has to ask, “Is it worth risking what I already have?”
Let’s walk through a concrete example using our narrative with John.
(14:13) Imagine you die with a Will that leaves money to your three children, including John. John receives the same dollar amount as his siblings—but there’s a difference. His share is left in trust. Your other two children receive their inheritances outright.
That means your other children have immediate, unrestricted access to the funds you left them. John does not. His inheritance comes with guardrails. A trustee must approve distributions before John receives anything.
Your Will also includes a no-contest clause.
After your death, John decides to challenge your Will. He claims you were pressured by his siblings, or that you weren’t thinking clearly when you made your estate plan.
The court reviews the case and ultimately rules: your Will is valid.
Because John’s challenge fails, the no-contest clause kicks in.
John doesn’t just lose the lawsuit—he also loses the inheritance you originally set aside for him in trust. His share is redistributed to his siblings as though John had predeceased you.
(15:16) If John had not challenged the Will, he would have remained a beneficiary of the trust you created for his benefit.
That’s how a no-contest clause works. It forces someone like John to weigh the risk of walking away with something versus gambling and potentially ending up with nothing.
So, circling back to question number one: should you disinherit John?
My general answer is no.
In this scenario, a more thoughtful approach is to leave John assets in a trust—managed by a professional fiduciary who has agreed to serve and has reviewed and accepted the trust’s terms. That trust can include appropriate provisions around sobriety, treatment, and what happens if there’s a relapse.
That approach protects John, protects your other children, and protects your estate plan.
Now let’s turn to question number two: If you do decide to disinherit John, how should you do it?
(16:15) If you intend to disinherit someone, your estate plan needs to say so clearly. Silence is not clarity. Silence invites litigation.
Clarity means explicitly naming John in your Will or trust and stating simply that you are intentionally leaving him nothing. Don’t explain why you’re disinheriting him. Just state that the disinheritance is a deliberate decision.
Second, make sure your decision is consistent across your entire estate plan.
It’s not enough to disinherit John in your Will if he’s still listed as a beneficiary on a retirement account, a life insurance policy, or a payable-on-death bank account. As I’ve discussed on previous podcast episodes, those designations override your Will.
Next, document your capacity and intent.
You want your plan created at a time when your capacity is clear and well documented. That may mean working closely with counsel, updating your plan proactively and making sure the process itself would hold up under scrutiny.
(17:24) Lastly, consider that complete disinheritance often increases the likelihood of a lawsuit, especially when the person being cut out has nothing to lose.
Leaving an amount in trust paired with a no-contest clause can be more effective than leaving nothing at all.
And remember this: disinheritance is not just a legal decision. It’s a relational one.
Ask yourself: What position does this put my other children in after I’m gone?
Will they become targets?
Will they become intermediaries?
Or will they be blamed for a decision that was never theirs to begin with?
A well-designed estate plan doesn’t just distribute money. It distributes responsibility. And you want to be intentional about where that responsibility lands.
(18:13) The best advice I can give you is this: do not leave your children to sort it out.
Do not create a situation that pits them against each other.
Do not leave a legacy where the most responsible child becomes sick with stress trying to fix pain they didn’t cause and cannot heal.
Yes, this takes more effort now. And it requires hard conversations. Your children may be angry with you.
But that’s okay. You can tolerate that. Your children have been angry with you before.
And when you do have these conversations, allow space for a child to disinherit themselves. Allow a child to say, I don’t want to serve as executor. I don’t want to be trustee. I don’t want to receive money under this plan.
Because saying no to money before it’s given is far easier than trying to refuse it later. Once money is left to someone, walking away from it is not just emotionally difficult—it’s legally complicated. That’s a conversation for another Tuesday Triage.
(19:16) Earlier, I mentioned that this episode was inspired by a LinkedIn post from California estate planning attorney Patricia De Fonte. In that post, she wrote:
“It is your role, as the parent, to protect all of your children from a trust battle and to try to leave a door open for them to find an improved relationship in the future.”
I agree with her completely.
This is your work to do now. You need to make space for this work and these conversations.
Your estate plan must be well coordinated. You need to understand which assets pass under your Will, which pass under a trust, and which pass by beneficiary designation or payable-on-death transfer. If you don’t know the answer to that, that’s your starting line.
In earlier episodes, I may have sounded less firm or urgent about this. But I’ve seen too many sibling relationships deteriorate beyond repair because of estate dynamics that could have been addressed ahead of time.
(20:13) You might think, My kids already don’t speak to each other. It doesn’t matter.
I promise you—it can get worse.
And it’s usually the most conscientious child, the one who already carries the most weight, who suffers the most. Not because they did anything wrong but because they’re left holding something they never asked to carry.
So what’s your next best step?
If you have an estate planning attorney you trust, start there.
If you don’t—or if you’re not sure your plan actually works the way you think it does—you can sign up for my estate plan audit. I’ll walk you through what you have, where the gaps are, and what changes might help you protect all of your children. Visit deathreadiness.com/audit to learn more. That’s deathreadiness.com/audit.
This is about responsibility.
And it’s about doing the hard work now, so your children don’t suffer needlessly later.
(21:11) If you have a question you’d like me to answer on a future Tuesday Triage episode, submit it at deathreadiness.com/tuesdaytriage. That’s deathreadiness.com/tuesdaytriage.
Thanks for listening today.
This is Death Readiness, real, messy and yours to own. I’m Jill Mastroianni and I’m here to help you sort through it, especially when you don’t know where to start.
Hi, I'm April, Jill's daughter. Thanks for listening to The Death Readiness Podcast. While my mom is an attorney, she’s not your attorney. The Death Readiness Podcast is for educational and entertainment purposes only. It does not provide legal advice. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state. To learn more about the services my mom offers, visit DeathReadiness.com.