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capital gains
America Needs To Tax Its Own 'Second Estate': Billionaires
The United States has no nobility, according to our Constitution. But our tax code does protect the very rich.
Dec 04, 2025
Pre-revolutionary French aristocrats—the “Second Estate”—didn’t pay taxes. Amazingly, America too has a second estate, billionaires who pay virtually no taxes. In her very outstanding recent book, law professor Ray D. Madoff shows how they get away with this.
The United States has no nobility, according to our Constitution. But our tax code does protect the very rich.
Federal taxes on income and estates—intended to fund government and prevent development of a hereditary financial aristocracy—were enacted early in the 20th century and originally worked well.
But since about 1980, the estate tax—infested with loopholes—has been nearly abolished for practical purposes and now produces trivial income.
Madoff wants to get rid of the ability of ultra-rich people—billionaires—to avoid having any taxable income in the first place.
Madoff suggests that the estate tax should be completely eliminated because its existence deceives the public about what is really going on. People falsely think that billionaires who pay no federal income tax will at least pay the estate tax when they die. In fact, they are paying neither kind of tax.
Billionaires avoid the income tax by arranging to have no taxable income.
Before 1982 ultra-rich people could not avoid paying income tax. Their income consisted of dividends and capital gains harvested by selling shares of stock, the price of which had increased. Dividends and capital gains are taxable income.
But in 1982 federal regulators weakened a rule prohibiting corporations from buying back their own stock. Since then, many corporations have used profits to buy back stock shares instead of issuing dividends. With fewer shares of stock outstanding and the value of the corporation increasing, the value of each share of stock began increasing dramatically.
What used to be taxable dividends turned into large capital gains benefiting the stock owners, including very rich ones. If shareholders need cash and sell appreciated stock, of course they would owe income taxes on the capital gains (selling price of the stock minus how much the shares cost them). But capital gains are taxed at a much lower rate than normal income like salaries, bank interest, and returns on bonds.
As Madoff points out, however, billionaires need not sell any stock to get cash to live on. Instead, they can borrow the money, using their stock as collateral. Borrowed money is not taxable income, so they owe no tax while living extravagantly.
And when they die, the stock they bequest to their heirs gets a stepped up “basis,” so if their heirs sell the stock they will owe no taxes because the stepped up basis leaves no taxable capital gains.
And inherited money is not considered taxable income. Someone who earns $50,000 pays significant income (and payroll) taxes on it, while someone who inherits $1 billion pays no income or payroll tax on it.
Madoff rightly objects to this situation, but she is not arguing that we should “soak the rich” with higher income tax rates at the top. She points out that there are two kinds of “rich” people. One is the working rich, skilled professionals earning high salaries and, usually, already paying very high taxes. A high percentage of all income tax receipts come from these people.
Increasing the high tax rates these “rich” people are already paying would produce insignificant extra revenue for the government.
Instead, Madoff wants to get rid of the ability of ultra-rich people—billionaires—to avoid having any taxable income in the first place. She wouldn’t tax them while they are alive, but would tax whoever inherits from them.
Rather than trying to fix the estate tax, Madoff would abolish it, eliminate the stepped up basis for inherited stock, and make inherited money and other gifts received taxable income for the recipients.
Assuming an exemption for small gifts (to allow birthday presents and the like), this could be a reasonable reform. It would bring in very large amounts of taxes while reducing today’s extreme economic inequality.
For further details, see Ray D. Madoff, The Second Estate: How The Tax Code Made An American Aristocracy. This is one of the two best books I have read since retiring in 2000.
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The Ultra-Rich Have Exploited Our Tax System Long Enough—Make Them Pay!
Funny how these same apologists for our richest don’t have much sympathy for ordinary Americans who lack the “wherewithal” to pay for medical care, adequate housing, and other necessities.
Mar 30, 2025
The most gaping loophole in our tax law? The tax-free compounding of gains on investments.
This classic loophole enables the two most lucrative inequality-driving income tax avoidance strategies. The first, buy-borrow-die, allows wealthy Americans to avoid income tax entirely on even billions in investment gains.
These wealthy need only hold on to their appreciated assets until death. What if they need cash before then? They merely borrow against the appreciated assets, typically at very low interest rates.
Are rich Americans, including billionaires, truly unable to pay tax on their investment gains before they sell the assets yielding those gains? Wanna buy a bridge?
The second avoidance strategy, buy-hold for decades-sell, lets wealthy investors pay a super low effective annual tax rate on investments that appreciate at high rates over long periods of time. These investors typically experience decades of compounding gains without taxation.
The effective tax rates involved in this second strategy won’t reach buy-borrow-die’s zero tax, but may in some cases get as low as a 4% effective annual rate. A 4% effective annual tax rate would have an investment with a pre-tax growth rate of 20% per year enjoying an after-tax growth rate of 19.2% per year.
Congressional apologists for the ultra-rich on both sides of the aisle regularly claim that their wealthy patrons should be entitled to endless tax-free compounding of investment gains. Without this tax-free compounding, the argument goes, our richest wouldn’t have the “wherewithal to pay” tax on their investment gains before their assets get sold. U.S. Sen. Ron Johnson (R-Wis.) invoked this tired canard at a recent Senate Finance Committee hearing.
Funny how these same apologists for our richest don’t have much sympathy for ordinary Americans who lack the “wherewithal” to pay for medical care, adequate housing, and other necessities. Average wage earners, under current law, can’t even wait until year-end to pay Uncle Sam their taxes. Those taxes come out of each paycheck, wherewithal to pay or not.
Are rich Americans, including billionaires, truly unable to pay tax on their investment gains before they sell the assets yielding those gains? Wanna buy a bridge?
Let’s start with the easiest case: a publicly traded investment that can be sold in smaller units, an investment in stocks, for instance. Say Rich, a wealthy investor, buys 1 million shares of Nvidia at $100 per share, and those shares, by year’s end, increase in value to $120 per share.
Our investor Rich now has a $20 million gain. If that annual gain faced a 25% tax rate, Rich would have a $5 million tax liability. To raise the cash to pay that tax, Rich could sell off 41,667 of his shares, leaving him with 958,333 shares, now worth just under $115 million.
That doesn’t seem very painful.
Now, let’s say Rich didn’t want to sell any shares. He could instead just borrow $5 million against the shares to pay the tax.
Or what if Rich had bought a parcel of land instead of Nvidia shares and, for whatever reason, having him borrow to pay tax on his annual investment gains didn’t turn out to be feasible?
Still no problem for Rich. For gains on illiquid assets, Rich could defer the payment of tax until he sold the assets, but the tax could be computed as if it accrued annually. How might this work? Say, for example, that Rich’s $100 million parcel of land grew at an annual rate of 10% for 20 years, at which point he sold it at its appreciated value of $672,749,995.
Had Rich paid tax at 25% on his gain each year, his rate of return would have been 7.5% per year, and after 20 years his investment would be worth $424,785,110.
The $247,964,885 difference between his sale price and the value of his investment with its actual rate of return reduced by the tax paid would be his tax liability upon sale. Payment of that amount would leave Rich with the same sum, $424,785,110, had he been able to sell a small share of his parcel each year, to pay the tax on his investment gain.
Put another way, Rich would be left with the same amount using this tax computation as he would if he sold his parcel each year, paid tax on the gain, and reinvested the remaining proceeds in another parcel.
And if Rich died before selling his parcel? His income tax could be determined for the year of his death in the same fashion as if he’d sold the parcel for its fair market value at the time of his death. Or, in the alternative, his inheritors could step into his shoes and pay the same tax when they sold the parcel as Rich would have had he survived and sold it at that time.
The bottom line: If we closed the tax-free compounding of investment gains loophole, some situations might exist where the immediate payment of tax on investment gains could pose a problem. But we can address those situations by deferring payment of the tax until investments get sold and accounting for the tax-free compounding in the determination of the tax.
These problematic situations, in other words, don’t justify leaving a gaping loophole in place.
So the obstacle to shutting down buy-borrow-die and buy-hold for decades-sell has absolutely nothing to do with ultra-rich investors lacking the wherewithal to pay taxes. That obstacle remains the politicians in Washington, D.C. who lack the wherewithal to summon the courage to make our rich pay the taxes they owe our nation.
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What Would Be a Truly Fair Way to Tax Capital Gains?
The Billionaires Income Tax proposal that Sen. Ron Wyden (D-Ore.) introduced last year would require billionaires to pay tax annually on the growth in their wealth—in the same way the rest of us pay tax on our salaries and wages.
Feb 19, 2025
America’s policymakers have been debating for decades now the fairness of the preferential tax rate for capital gains. The maximum federal income tax rate applicable to long-term capital gains currently sits a whopping 17 percentage points lower than the maximum rate applicable to ordinary income: 20% on long-term gains versus 37% on ordinary income.
Let’s note here at the outset that both ordinary income and capital gains may be subject to federal employment tax or the net investment income tax. But including those additional taxes does not change the essential tax-time gap between ordinary and capital gains income. So, for simplicity’s sake, let’s just here consider the gap between the 20 and 37% rates.
Eliminating the preferential rate for capital gains, many analysts maintain, would finally place investment income and wages on an equal footing tax-wise. But would that actually be the case? Unfortunately, no. Simply equalizing the basic tax rates on ordinary and capital gains income would leave in place the gaping “buy-hold for decades-sell” loophole.
If you had to choose between paying tax at 10% annually or paying 10% every 10 years, would you consider those two rates equal?
The framing of the debate over the current preferential treatment for capital gains makes this loophole quite difficult to notice. And that same framing leaves us accepting, incorrectly, the implied premise that the low nominal tax rate rich investors pay on their capital gains—barely half the rate applicable to other types of income—accurately describes the tax rate in an economic sense.
If we continue to focus solely on whether the 20% rate applied to billionaire gains should be raised to 37%, in other words, we won’t be questioning that accuracy.
A similar phenomenon arises when we’re discussing billionaire wealth. Most of us see the obscene fortunes of the world’s billionaires, as reported by Forbes and Bloomberg, and seldom consider the possibility that many of those fortunes may actually be higher than the published estimates. But think a moment: If you held a billion-dollar fortune and wanted to keep your tax bill as low as possible, would you want policymakers knowing the full extent of your wealth? Of course not.
But most of the rest of us don’t ask that question. We see a deep pocket’s wealth estimated at, say, $50 billion—about 50,000 times more than our own $100,000 net worth—and the last thought to enter our minds would be that this deep pocket’s wealth might really stand at $75 billion.
Just as the bloated level of estimates of billionaire fortunes causes us not to consider the possibility those fortunes may be actually even larger, the low tax rate nominally applicable to capital gains income leaves us unlikely to fully compare tax rates on ordinary and capital gains income.
The key to understanding how to make better comparisons: taking tax frequency into account.
Most of the income Americans make—wages and salaries, most notably—gets taxed annually. Capital gains, by contrast, get taxed only when the holders of investment assets decide to sell them. That reality turns a simple comparison of the 20% tax rate on capital gains with the 37% top tax rate on ordinary income into an apples-to-oranges comparison.
Or to put things another way: If you had to choose between paying tax at 10% annually or paying 10% every 10 years, would you consider those two rates equal?
We can overcome the difficulty in comparing the tax rates on ordinary and capital gains income once we begin to understand why we cannot consider these two situations the same.
Consider, for starters, what your tax liability would be if you inadvertently understated your income from a small business on your tax return by $50,000 and then reported the missing income three years later. You would end up paying the IRS not just the tax you should have paid on that income, but an interest charge as well—for deferring the payment of tax beyond the year you earned your income.
For the sake of discussion, let’s say you were required to pay $10,000 in tax and $2,500 in interest. You would then have paid tax at an overall 20% rate.
Now compare that to the situation your rich friend encountered. She invested $50,000 in stocks and held that investment for four years. Say that investment doubled in value, to $100,000, in the first year—the same year you earned the $50,000 of income you failed to report—and then held that value for another three years. If your friend then sold her investment and paid tax at the 20% rate applicable to capital gains, she could claim to have paid tax at the same 20% rate you did.
But would that be accurate? Not really. Economically, your friend has obviously paid tax at a lower rate than you. Yes, you both realized $50,000 of income in the same year and you both paid tax on that income three years later. But you paid a total of $12,500, including interest, while she paid only $10,000.
What happened here? Economically, your friend’s $10,000 tax payment includes a charge for the privilege of deferring the payment of tax. By contrast, our tax system considers your $2,500 deferral charge on your $10,000 obligation a separate item. To make the comparison apples-to-apples, then, we might consider your friend to have paid tax at an effective annual rate of 16%, $8,000, plus a $2,000 deferral fee.
Now consider the case where you received your $50,000 of income—along with additional income necessary to place you in the top marginal tax bracket—in the same year your friend sold her $50,000 investment for $100,000, rather than the year she purchased it.
You would have paid tax on your $50,000 at the marginal rate of 37%, a total of $18,500—and likely have been laser-focused on having had to pay nearly double the tax rate that your ultra-rich friend paid–37% versus 20%—on the same $50,000 of income. In all likelihood, you would at the same time have failed to focus on the reality that the 20% rate applied to your friend’s gain actually overstated the rate she paid in comparison to the rate you paid.
Let’s expand our financial horizon. Say a rich investor purchases an asset for $1 million. Over the next 30 years, that asset grows in value at a steady pace of 10% per year, an average-ish return for a rich American investor. At the end of the 30 years, the asset would be worth about $17,450,000. If the investor then sold the asset and paid tax at 20% on the $16,450,000 gain, a total tax of $3,290,000, he would be left with about $14,160,000.
Suppose instead our investor had to pay tax annually on each year’s investment gains at the rate of just 7.65%. Suppose our investor each year sold a portion of the investment sufficient to pay the tax liability. At the end of the 30 years, the investor will have paid a total of $1,090,000 in tax and be left with the same amount, $14,160,000, that he would have been left with after paying tax at 20% upon a sale in year 30.
Why the $2,200,000 difference between the $3,290,000 total paid when taxed in year 30 and the $1,090,000 total paid when taxed annually? In economic terms, that’s what the investor paid for the privilege of not paying tax until year 30. In other words, interest.
Removing what economically amounts to a charge for the privilege of deferring tax allows us to make an apples-to-apples comparison. The investor effectively has paid tax at a rate of 6.63%. That’s a 30.37 percentage-point difference between the investor’s effective rate of tax and the 37% top tax rate on ordinary income.
How much would that 30.37 percentage-point gap be reduced if the investor’s $16.45 million gain were taxed at a 37% rate when he sold his investment after 30 years? About five percentage points. Of the investor’s 37% nominal tax rate—using the same method of analysis—about 25.34 percentage points would constitute interest, leaving only 11.66 percentage points, economically, as tax.
Should we equalize the tax rates applicable to capital gains and ordinary income? Absolutely. But let’s not kid ourselves. Making that change will not remotely eliminate the preferential tax treatment accorded to capital gains. We need a further change, at least for the billionaire class.
The Billionaires Income Tax proposal that Sen. Ron Wyden (D-Ore.) introduced last year would require billionaires to pay tax annually on the growth in their wealth—in the same way the rest of us pay tax on our salaries and wages. It’s high time to close the “buy-hold for decades-sell” loophole. Sen. Wyden’s Billionaires Income Tax would be one way to do just that.
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