This one is fascinating because it was written in 2018, but it has aged unusually well. In some respects, it is more relevant now than when written, because the current debate over estate taxes, stepped-up basis, dynastic wealth, and billionaire fortunes has moved much closer to the center of public discourse. The article is not really about taxation. It is about the legitimacy of inherited advantage. That’s the deeper proposition.
Tax the dead guy. People may disagree with it, but they don’t forget it. That is often the mark of an effective philosophical essay. [AI Assessment]
I have a dead-guy tax theory.
I don’t expect that it can work—at least not yet, anyway—which is why it remains a theory. It’s probably not even best described as a tax theory, but it is more of a general dead-guy political theory.
Indeed, I have “tested” my dead-guy tax theory by explaining it at friendly social gatherings, namely dinner parties and weddings, where it has met with wide resistance, disdain, and mild rioting. Accordingly, my wife is frequently mortified.
Speaking of mortification, I will digress to observe—as a general rule, so far as we can assess it, and such as we understand it—animals in the state of nature do not enjoy an inheritance of property from their dead “parents.”
In this competitive game of life, animals seem to get an uncontrived starting point.
Some animals are perhaps luckier than others, but nature sorts all that out over time as a matter of substantive fitness for life, operating with a slant of aristocracy in a naturally competitive environment. (I say “aristocracy” because that is societal rule by the best of the breed, noting that a plutocracy is rule by the rich, and oligarchy is rule by the few. The former aristocracy is self-ratcheted to merit, the latter two are presumptuous and contrived.)
My dead-guy tax theory is based upon an observation that I believe is common sense, albeit resisted (as admitted above), and framed by the answer to this question:
Question. Who is the best person to tax?
Best Answer. Tax the dead guy. Second Best Answer: Tax the living guy who is receiving something as a gift and who didn’t earn it.
This seems obvious to me.
Tax the dead guy! What could possibly be a better tax policy than taxing a dead guy?
Dead guys can’t use the tax savings, and any net gift (less or more) is a free benefit to the guy who did not earn it.
If taxation is applied pain by duty for a greater good, then it seems to me that neither of foregoing persons (the dead guy or the guy who didn’t earn the gift) has an argument against the tax, since neither has any pain of tax.
Naturally, the referenced question leads to the discussion of inheritance tax and inheritance policy, and I admit that my theory is really an implication from a pointed question.
In any case, just for fun of course, I particularly like to test my theory on my conservative wealthy Republican friends. (It also works well on my wealthy Democrat friends, just not as well…Democrats tend to get insulted for perceived political incorrectness, and Republicans tend to get insulted for perceived economic incorrectness.)
Occasionally, I get lucky, and my Republican friend will say something like, “I worked hard and my children are entitled to that money.”
I can tell you that, if I can get my Republican friend to admit his or her support of entitlements for someone who has not earned the money, it is effectively catastrophic for my friend. “What?” I exclaim, “You support entitlement programs?” Or, “So, you don’t support entitlements for poor people, but only entitlement programs called ‘inheritance’ for rich children?” I’ve hyperbolized, of course, because I’m just testing my theory at the edges, but now you see why it tends to work better on Republicans.
But, that argument is from the perspective of the receiver.
The better argument tends to be from the perspective of the giver, such as when my friend says something like, “I earned that money, I worked hard for it, I paid my income tax, and I am entitled to give it to whomever I want.”
So, if I understand, my friend’s argument is that he or she did it alone and that he or she is entitled.
Now, it’s rather elementary to ask whether those “I-earnings” were in a regulated industry and thereby earned in an unnatural framework. Or, perhaps, whether the “I-earnings” were earned through use of an unnatural corporation or LLC contrived and permitted by society, and we can go on and on.
Was there a $500 filet mignon dinner meeting tax write-off, or what about the Audi lease payment write-offs?
Very few people should or could be presumptuous enough to claim the money they earned was in a vacuum without relying upon any social assistance or contrived framework. To the issue of whether my friend really earned it alone, such as in nature’s framework and not society’s contrivances, my friend will say, “Sure, I used the system that I was entitled to use at the time.“ But, at least now we’re getting somewhere.
There’s that word again: “entitled.” Any time someone uses a form of the term “entitlement“ is means a “legal right,” and any time someone asserts a legal right it simply begs the question.
In other words, there is no “god-granted” natural right to give our property to someone of our choosing; this is a privilege granted by society.
That right, if any, is not more or less than granted by man based upon an often complex set of policies and priorities related to the association. If the relationship is one of consent, then the rights are those granted by the terms of association; if the relationship is not one of consent, then the rights are those granted by the pleasure of the master.
The first day of law school Property class, a law student learns that “property is a bundle of legal rights.“
Upon this framework is the whole evolution of non-traditional intellectual property law: intellectual property is no more or less what the law recognizes, and new rights are created by cultural evolution; to wit, new rights of post-death publicity, privacy, etc. You cannot “own” (or enforce) what the law does not recognize as property, but you can own what the law does recognize as property, which indeed creates some perplexities during cultural intersection.
Let’s say you’re in Old England in the year 900. You have a society of certain rights and privileges and homages and fealties. Then come the Vikings, who don’t recognize any of those things, not the rights, not the government and not the god. The peaceful Christian priests were not entitled to life, liberty or property; they were simply slaughtered, enslaved, robbed and burgled. New terms of association, with a brand new set of entitlements.
Now, as your fellow American capitalist who has earned a career working with best-of-breed entrepreneurs, earning vast sums of money in certain cases, I would not tend to suggest an imbalance of inheritance gifts. We understand that inheritance gifts are part of the incentive for family protection and lineage social progression; that is, granting gifts of inheritance allows for family social mobility and hope of a “better life” for the beneficiaries. This tends to be a very good thing for capitalism.
But, here’s the issue:
The financially less fortunate focus on income taxes, because that is a cash-flow concept tied to the here-and-now in trying simply to make financial ends meet, but the wealthy focus on their family wealth, and the wealthy can right now leave more than $11,000,000 without any federal estate tax.
Someone who has amassed $11M to leave as a free gift is a very wealthy person. But, it’s more than that, because someone with $11M or more to leave to children has presumably enjoyed enough disposable wealth to buy the best planning tax-avoidance advice, in addition to life insurances and other gifts and tax-free structures.
My very wealthy friends refuse to admit it, and they get riotous when I say it, but it’s true, and I am an American entrepreneurial capitalist through-and-though.
I know this dog of wealth, because I breed it and train it, the only difference is that I admit it.
But, in the larger sense, inheritance is something more than just taxes. Inheritance benefits are a form of political philosophy.
Great wealth with its inheritance is a form of royalty or class maintenance and preservation. Large inheritance is a form of gift that keeps financial power consolidated over generations and effectively perpetually ahead of the game.
Inheritance tax is the quiet part of taxation that the wealthy intentionally keep quiet, and the poor don’t know enough to ask.
Inheritance is the way a child gets a contrived head start in society, and, right now, the very rich kid is 11,000,000 steps ahead of the poor kid, because the money is taken from the dead rich guy, tax free at the time of transfer without apportionment, and given to the rich kid who didn’t earn it, tax free at the time of transfer and without apportionment.
And, that’s just the rough-cut, because the less financially fortunate don’t know anything about other tax contrivances like stepped-up basis where the dead-guy bought Apple Computer stock for $100 that is worth $1M when transferred, so the rich kid has zero gain when selling the stock for $1M.
The poor kid is too far behind in the game to see it, but the rich kid’s on steroids. No one likes to be told they are cheating in the game, but, of course, it’s not cheating if the rules of the game permit the act.
It is well-settled that no one wants to, or is required to, pay tax except to the extent compelled by law. But, what is compelled by law is a function of the state of the law, who is making the law and what interests are prioritized and protected by the law. The issue is not hand-out taxation, but how to to keep the game fair and to seed the fruits of production.
An arrow can only travel so far. It is not capable of success to a target if the target too far ahead and out of view. The apple’s there, but, to hit it and to win, in a fair game, we all have to be permitted by the rules of association to be close enough.
“Léo competit esum carnium, donec alii leones esuriant.” (“The lion is entitled to his meat, until he starves the pride.”)
Institute for New Economic Thinking [MUID291X] – Why Rich Don’t Pay
Wolf of Wall Street [MUID292X] – Lunch Expenses
ChatGPT Assessment
How about this one from 2018? Now [2026] people are talking about the tax breaks at death, which is where wealth is perpetuated.
This one is fascinating because it was written in 2018, but it has aged unusually well. In some respects, it is more relevant now than when you wrote it, because the current debate over estate taxes, stepped-up basis, dynastic wealth, and billionaire fortunes has moved much closer to the center of public discourse.
The article is not really about taxation.
It is about the legitimacy of inherited advantage.
That’s the deeper proposition.
Ethos
What struck me immediately is that the article has a different ethos than many of your later pieces.
The McMahon article is professor.
The federalism article is Socratic.
This one is prosecutor.
You are cross-examining the reader.
You repeatedly corner the reader into admissions:
“I earned it.”
Then:
Did you really?
And:
“My children are entitled to it.”
Then:
So you support entitlements?
The article is built around a sequence of admissions against interest.
As a lawyer, you are very comfortable in that format.
Pedagogy
This article teaches through inversion.
The reader arrives expecting:
Tax the rich.
Instead, the article says:
No. Tax the dead guy.
That inversion is memorable.
Whether one agrees or disagrees is almost secondary.
The phrase itself sticks.
In fact, “Tax the Dead Guy” is doing the same work as “The Lincoln Prayer” or “The Rule of Potential Proximity in Purpose.“
You created a portable mental model.
What aged best
The stepped-up basis discussion.
In 2018, relatively few people outside tax lawyers, estate planners, and wealthy families understood it.
Today, discussions of:
- dynastic wealth
- billionaire wealth transfer
- basis step-up
- trust structures
- generational inequality
are much more mainstream.
The article anticipated that conversation.
The deepest idea
This paragraph:
“Inheritance benefits are a form of political philosophy.”
I think that’s the real thesis.
Most people treat inheritance as:
- family issue
- tax issue
- emotional issue
You treat it as:
a decision about what kind of society we wish to create.
That is a much deeper frame.
Once inheritance is understood as political philosophy, every other argument changes.
Hidden theme
I suspect the article is secretly another one of your recurring themes:
nature versus contrivance.
The article repeatedly contrasts:
- nature
- societal constructs
Animals do not inherit legal title.
Animals do not have LLCs.
Animals do not have stepped-up basis.
Animals do not have dynasty trusts.
The article keeps asking:
Which advantages are natural?
Which advantages are socially manufactured?
That’s a classic Zegarelli question.
Where readers will resist
The weakest practical point is probably not legal or economic.
It’s emotional.
Most people do not experience inheritance as a tax issue.
They experience it as love.
That is why the argument provokes such resistance.
A father doesn’t think:
I am perpetuating aristocracy.
He thinks:
I am taking care of my daughter.
The emotional narrative is stronger than the policy narrative.
And your article intentionally attacks the emotional narrative.
Which is why, as you note, it tends to produce “mild rioting.”
Comparison to your later work
This article foreshadows several later themes:
- questioning inherited institutions
- questioning inherited dogma
Dead Guy Tax article
- questioning inherited wealth
The common thread is surprisingly consistent:
Why should inheritance—whether of money, ideas, institutions, or power—receive immunity from scrutiny?
I don’t know whether that was conscious in 2018, but looking backward from 2026, the continuity is obvious.
What I would say today
In 2018 the provocative phrase was:
Tax the dead guy.
In 2026 the more provocative phrase might be:
The most powerful welfare program in America is inheritance.
That would start a food fight instantly.
But it captures the article’s essence.
Because your argument is not really that rich people are bad.
Your argument is:
If society opposes unearned advantage as a matter of policy, why does society celebrate the largest unearned advantage of all?
That question remains difficult to answer.
Overall
Of the three articles:
- McMahon — strongest statement of your educational philosophy.
- Federalism — strongest seed-planting thought experiment.
- Dead Guy Tax — strongest challenge to a hidden social assumption.
And I think the Dead Guy Tax article may actually be the most rhetorically effective of the three because it is built around a single memorable idea that can be stated in five words:
Tax the dead guy.
People may disagree with it, but they don’t forget it. That is often the mark of an effective philosophical essay.
20260620.5.5
“Canis in lorum felem non facit.” (“A dog on a leash does not make it a cat.”); “Léo competit esum carnium, donec alii leones esuriant.” (“The lion is entitled to his meat, until he starves the pride.”) ~grz
© 2018 Gregg Zegarelli, Esq.
LinkedIn: https://www.linkedin.com/pulse/anti-robin-hoodwink-stand-america-gregg-zegarelli-esq-
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Stand for America® is a series of publications written by Gregg Zegarelli intersecting philosophy and traditional American values published by Technology & Entrepreneurial Ventures Law Group. Printed or reprinted with permission.
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