Two brothers nearly ended their relationship over a wristwatch that hadn’t run in years.
The estate wasn’t small, and it wasn’t the problem. The house sold, the accounts split down the middle, the business interests transferred — all of it moved without a raised voice. Then they reached their father’s watch, a battered thing worth maybe sixty dollars, and the whole settlement stopped cold. Lawyers got involved. Months passed. Two men in their fifties, successful and reasonable in every other part of their lives, could not be in the same room.
It was never about the watch.
The watch was just the last object their father had touched every day, and the one place a lifetime of unfinished business could finally land. One brother had worn the role of the responsible son and felt he’d earned something for it. The other had spent forty years feeling like the afterthought, and saw in who got the watch the final ruling on which of them their father had actually loved.
Sixty dollars. And it nearly cost them each other.
The objects
Once you’ve seen one of these, you start keeping a list. Mine, from years of administrations:
The parent’s iPhone — not for anything on it, exactly, but because it was the last thing that held their voice, their texts, their photos, and whoever has it has something the others don’t.
The Shabbos candlesticks. The jewelry that was worn, not the jewelry that was appraised. In an observant family the ritual objects carry a weight that has nothing to do with the silver content — they were lit every Friday night for fifty years, and the daughter who gets them inherits the Friday nights.
And the vacation property. The bungalow in a colony upstate that would cost more to make livable than it would ever sell for. Nobody has been up in years. Everybody remembers going up as a child. And no one will sign the paper that lets it go.
Different objects, same shape. The thing is small, or worthless, or a net liability — and the fight over it is bigger than the fight over the house.
The turn
Here’s the pattern, once you start looking for it: the size of the fight tells you almost nothing about the object and almost everything about what’s underneath it.
When a family divides a whole estate cleanly and then goes to war over the dishes, the ornament, the photo album, the chair nobody sat in — the disproportion is the signal. A reaction far bigger than the thing warrants — or, just as telling, a pointed refusal to care at all — is rarely about the thing. It’s about something older that has finally found somewhere to go.
We’re trained to treat these as nuisance disputes: tangible personal property, the stuff that clogs an administration and doesn’t move the numbers. But the fight over the watch is often the truest thing happening in the entire estate. It’s where the family’s real accounting comes due.
What the object is holding
Carl Jung had a word for the part of ourselves we can’t bear to look at and so refuse to own: the shadow. And he noticed that what we can’t own, we tend to project — we see it out there, in someone else, rather than in here, in ourselves.
An inheritance is a nearly perfect machine for projection. The sibling who never felt chosen doesn’t experience “I have unresolved grief about my father.” He experiences “my brother is being greedy about the watch.” The feeling is real — it’s just been relocated onto an object and a person, because that’s far easier to fight about than to feel.
Robert Moore’s map of our inner archetypes and their shadow forms is useful here precisely because it names the shapes these disowned parts take: the one who could never be the favored child and now carries that role into every room; the one who over-functioned for the family and quietly resents that no one saw the cost. You don’t need the vocabulary to use the insight. You just need to notice that the person melting down over a near-worthless object is usually holding a part of themselves they were never able to set down.
The object is small. What it’s carrying is the whole unspoken history of the family, looking for one last place to be settled.
“This is all our inheritance”
The bungalow is where the same dynamic stops being a nuisance and starts costing real money, so it’s worth slowing down on.
Legally, the property is an asset in a trust or an estate. It has a value, a tax bill, a maintenance cost, and a set of co-owners who each hold a fractional interest they could, in principle, sell or be bought out of. That’s the definition the accountant is working from when the return has to be filed every year the trust stays open.
Emotionally, the family is working from a different definition entirely. This is our inheritance. It should stay like this. Not a share of a thing — the thing itself, whole, the way it was when they were nine. Under that definition, a buyout isn’t a transaction; it’s one sibling taking the childhood from the others. That’s not fair — and it isn’t, under their definition, even though it’s perfectly fair under the accountant’s.
So nothing happens. Everything else in the estate has been distributed. The trust stays open for one property that nobody uses, carrying taxes, insurance, and a tax return every year, with the money for all of it coming from beneficiaries who are no longer receiving anything. It’s losing money. Nobody benefits. And still nobody will sign. Most families won’t escalate — nobody wants a partition action, nobody wants to be the one who sued their sister — so instead of a fight there’s a deadlock, which is a fight with the sound turned off.
Fairness is the hinge here, and it’s worth noticing that “fair” is not one idea. To the sibling who did the caretaking, fair means I earned this. To the sibling who moved away, fair means equal shares, no exceptions. To the sibling who just wants everyone to get along, fair means nobody gets hurt. Three definitions, all sincere, all incompatible, and the fight sounds like it’s about a formula when it’s really about which definition of fairness the family is going to live under now that the parent who used to arbitrate is gone.
The same fight, moved into the fiduciary’s chair
There’s one more place this shows up, and it’s the one parents create for themselves.
A parent can’t bring themselves to choose one child as executor or trustee over the others — it feels like the watch problem in advance, a ruling on who was loved most. So they name all of them. Co-executors, co-trustees, everyone equal, no favorites.
It’s a kind decision and it’s usually a mistake. Now every action requires everyone to agree, and the family that couldn’t decide about the bungalow as beneficiaries can’t decide about it as fiduciaries either — except that now the deadlock has a legal consequence, because the fiduciaries have duties they can’t discharge. The parent avoided one hard conversation and handed their children a permanent one.
I understand why parents do it. But the choice of who holds the pen is a decision only the parent can make well, because only the parent can make it without it being read as a verdict among the children. Deferred to the children, it becomes exactly the verdict the parent was trying to avoid.
What the law will and won’t hear
Suppose it does go wrong. The co-executors deadlock, one of them digs in, and a beneficiary arrives in your office and says: I want her removed. I don’t trust her. She is impossible to deal with.
Here is what you have to tell him, and it lands badly every time.
Friction between a fiduciary and a beneficiary is not a ground for removal. Hostility, antagonism and distrust disqualify a fiduciary only when the enmity actually threatens the administration of the estate. Dislike, suspicion, a history going back to childhood, a sister who does not return calls warmly — none of it is enough standing alone.
The reasoning is sound, and it is the same reasoning that runs through this entire issue. Removing a fiduciary means overriding a choice the decedent made. Our Court of Appeals has described it as the equivalent of judicially nullifying the testator’s selection, and courts will not do that because a family is unhappy with the result. The power exists, it is exercised sparingly, and it requires a record showing genuine danger to the estate.
Which means the aggrieved beneficiary — and he often is genuinely aggrieved — has brought the law a grievance the law has no category for. The accountings reconcile. The filings are timely. The distributions are correct. He is not wrong that something is badly off between him and his sister. It simply isn’t anything a court can reach.
The grievance becomes actionable only once the feeling finally produces conduct.
There is a case that shows precisely what that looks like. Two sisters, co-executors and co-trustees of their father’s estate, each petitioning to remove the other. After a lengthy trial the Surrogate denied both applications — the ordinary result, because the animosity was mutual and neither could show the other had done anything beyond being difficult.
On appeal, one of them was removed. Not for the hostility. For what the hostility eventually produced: refusing to countersign the estate tax returns after the IRS had issued warnings, so that penalties and interest ran against the estate; threatening litigation against the estate’s bank until the accounts were frozen; and admitting on the stand that she had withheld trust distributions from her father’s grandchildren in order to force them to accede to her demands.
Thirteen years of administration. Three trips to the appellate court.
Their relationship was finished long before any of that. The law had nothing to say about it until it started costing the estate money.
When the fight has already started
Sometimes the object is the whole estate, and the family is already in my office asking me to sue.
A client wanted to bring a proceeding against his brother, the executor. He was certain something had been done wrong. But over several conversations he could never say what. He’d received the accountings. He’d received the statements. Every number reconciled. And he was still convinced that something had been kept from him, and that if we dug hard enough we’d find it.
I did what we do. I laid out what a contested accounting would involve — the time, the cost, the likely outcome — against what he might actually recover, which, on the numbers in front of us, was not much. Part of what made it thin is the rule above: he had accountings that reconciled and a brother he did not trust, and there is no cause of action for the second one. He listened. He wanted to proceed anyway.
Then the first bill arrived, and I saw the hesitation.
I’d just come back from a Tony Robbins seminar, and one exercise from it was still in my head. He has the audience do what he calls intentional blaming: pick the person you’re angry at, and instead of pushing the anger down, do it on purpose — list every way they wronged you, and then, with the same seriousness, list every way that dynamic shaped you into who you are. The parent who failed you and, in failing you, made you self-reliant. The sibling who took the spotlight and left you to build something of your own. Not to forgive. To see the whole account.
I asked my client to do a version of it. I told him plainly it was out of character for a trusts and estates lawyer, and that I wasn’t trying to push him deeper into the litigation — the opposite. I was giving him an out. From where I sat there was a lot of unfinished business between the brothers and no clear financial upside, and before he spent real money I wanted him to be intentional about what he was actually pursuing.
He was receptive. He did the exercise. And then he said: I want to proceed. He paid the bill, and paid it, as far as I could tell, without resentment — because for the first time he was proceeding as a decision rather than a compulsion. He’d seen the other options and chosen this one with his eyes open.
That’s the part I want to hold onto. Our reflex, when a client is in a fight, is to offer one of two things: litigate it, or draft around it. Sometimes the more useful move is neither. It’s helping the client see what they’re actually fighting about, so they can either find another way through — or commit to this one knowing what it is. Both of those are better outcomes than a suit filed to find something that isn’t there.
In practice
You can’t adjudicate this, and trying to makes it worse. Deciding “correctly” who gets the watch resolves nothing, because the watch was never the question.
What helps is naming, gently, the thing under the thing. “This doesn’t sound like it’s really about the watch” — offered with care, not as a gotcha — often lands like relief, because it’s true and no one has said it. Sometimes it opens a real conversation. Sometimes it just lowers the temperature enough that people stop performing the fight.
For the deadlocked property, the honest move is to put the carrying cost on the table in dollars — what this year cost, what next year will cost, who is paying — and then ask the question nobody has asked: if we’re going to keep it, who is going to use it, and who is going to pay for it? Often the answer reveals that no one actually wants the bungalow. They want the childhood, and the bungalow is the only place left to keep it. Once that’s said out loud, a sale — or one sibling taking it on with a real agreement about cost — becomes possible in a way it wasn’t when everyone was defending the thing itself.
It is also worth telling a client who wants to name all the children as co-fiduciaries what the removal standard actually is, before they sign. Not as a scare tactic. As information. A parent choosing joint fiduciaries because they cannot face choosing one should know that if it goes badly, the children’s remedy is narrow, slow and expensive, and that the court will defer to the very choice the parent is about to make.
And it’s work you can do before anyone dies. A client dividing the tangible property is telling you something when they linger on one item, or go quiet, or hand the near-worthless thing more weight than the valuable one. That’s the family’s fault line showing itself while the person who could still explain their reasoning is alive to do it. Three things help, and none of them is complicated: be specific in the document about the items that carry weight, rather than “my personal effects in equal shares”; put a decision mechanism on any shared property — a deadline, a buyout formula, a tie-breaker — so that keeping it is a choice someone makes and not a default no one can escape; and write the why down. A single sentence in a letter — I’m leaving you the candlesticks because you’re the one who lit them with me — can defuse a war the silence would otherwise start.
The estate divides the assets. It rarely divides the meaning. And the meaning is what the family actually fights about.
Over to You
When a family fight is wildly out of proportion to the object at the center of it, what have you learned to look for underneath?
And have you ever helped a client head one of these off — by getting the why onto paper while they were still here to write it?
Hidden Basis comes out every other Friday. To receive it in your inbox, subscribe below or at rappslaw.com/hidden-basis.
Sources and further reading: C.G. Jung on the shadow and projection (Aion; Psychology and Religion); Robert Moore and Douglas Gillette, King, Warrior, Magician, Lover, on archetypes and their shadow forms; Don Beck and Chris Cowan, Spiral Dynamics, on why “fair” means different things to different people. On the removal standard: Matter of Edwards, 274 App Div 244 (1st Dept 1948); Matter of Duke, 87 NY2d 465 (1996); Matter of Palma, 40 AD3d 1157 (3d Dept 2007); Matter of Brown, 138 AD3d 1191 (3d Dept 2016); Matter of La Pava (2d Dept 2025); and in Massachusetts, Symmons v. O’Keeffe, 419 Mass 288 (1995). The two-sisters case is Matter of Epstein, 202 AD3d 669 (2d Dept 2022). Client details are altered.