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tax avoidance
How Billionaire Tax Avoidance Works: The Case of Jeff Bezos
Billionaire tax avoidance stems directly from the reality that America’s tax on capital gain income remains a steeply regressive tax.
Jul 30, 2025
The recent wedding of Jeff Bezos and Lauren Sánchez in Venice set off quite the furor over tax avoidance. An enormous banner in the Piazza San Marco put the matter plainly: “If you can rent Venice for your wedding, you can pay more tax.”
That banner prompted a commentary from Phoebe Liu at Forbes on how much tax Bezos does indeed pay. For the year 2024, according to a Forbes estimate, Bezos paid about $2.7 billion in tax on the gain from his sale of $13.6 billion worth of Amazon stock. That stock—the heart of the Bezos fortune since he started Amazon in 1994—originally cost him no more than $13,600.
In other words, some 99.9999% of the proceeds of the Bezos stock sale last year counted as a taxable long-term capital gain. This Forbes tax estimate took into account charitable contributions of Amazon stock that Bezos likely claimed as a 2024 deduction.
The Bezos $2.7 billion income tax payment, Liu noted in her Forbes analysis, represented only 4.5% of the 2024 increase in his personal net worth—approximately $60 billion—and barely more than 1% of his overall $230 billion net worth.
We have a tax system, in short, that favors the wealthiest Americans and fosters extreme wealth concentration.
Props to Liu for her reporting. She has helped shine a light on how undertaxed America’s billionaires have become even in years when they pay billions of dollars in tax.
But I wonder: What would the reporting have looked like if Bezos had sold all $200 billion or so of his Amazon stock? Would we be reading that he paid $40 billion in tax—a sum equal to over 20% of his net worth—with a suggestion that he paid his fair tax share? Yeah, we probably would. Not necessarily from Liu, but apologists for the ultra-rich would have been all over it.
Which raises the question: Should our view of how much the ultra-rich pay in tax turn on how much of their investments—as a share of their total wealth—they sell in a given year or on how much their overall wealth happens to increase in that specific year?
Bezos, for example, has sold over $600 million of Amazon shares so far this year, with the apparent intention to sell a bunch more. The value of Amazon shares this year has not increased much. He may well pay more in tax on those sales than his wealth increase for the entire year. Would that mean he’s overtaxed? Of course not.
So how can we better understand billionaire tax avoidance? By focusing only on billionaire taxable transactions, without reference to irrelevant data such as their total wealth or the annual increase in their total wealth.
Consider just the Amazon shares Bezos sold last year, shares worth an astounding 1 million times what he had paid for them 30 years earlier. The average annual increase in the value of those shares, when you do the math, turns out to be 58.5%, an incredible performance.
Now assume Bezos paid the full 23.8% tax rate on his gains, without taking those charitable contributions into consideration. That would leave him with $10.36 billion after tax, a total that translates to an after-tax average annual rate of increase of 57.1% and a reduction of less than 2.5% from his pre-tax annual rate of increase.
This means that the maximum federal income tax Bezos could have paid on the gain from his 2024 Amazon stock sales amounts to the same end result as would an annual tax on the increase in value of his Amazon shares of 2.5%, assuming the tax were paid from sale of the stock. And the result would be the same—an effective annual tax rate of 2.5%—had Bezos sold all his Amazon shares last year or if 2024 happened to be a year when his wealth didn’t increase much.
Tax avoidance by billionaires, these numbers help us see, doesn’t essentially come from the amount of income these rich report in a given year compared to their wealth or even the amount of income they report in a year compared to that year’s increase in their wealth. Billionaire tax avoidance stems directly from the reality that America’s tax on capital gain income remains a steeply regressive tax.
As I’ve noted previously, the longer a deep pocket holds an investment and the greater the annual rate of increase in value that investment yields, the lower the effective annual federal income tax rate will be when the investment finally gets sold. The effective annual tax rate on long-term, high-yield investments can end up at less than one-fifth the rate on short-term, low-yield investments.
More than all other taxpayers, our wealthiest find themselves easily able to hold investments for long periods of time. We have a tax system, in short, that favors the wealthiest Americans and fosters extreme wealth concentration.
And if we can’t figure out how to reform that tax system soon, heaven help us.
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How Big Oil Lobbied Its Way Out of Accountability for the LA Fires
"Accountability is an existential threat to their business model, and their business model is an existential threat to all of us, and that’s the bottom line," said Meghan Sahli-Wells, the former mayor of Culver City.
Jan 15, 2025
As devastating wildfires continue to burn in the Los Angeles region on Wednesday—placing tens of thousands of Californians under evacuation orders and causing over $250 billion in economic damages by one estimate—a pair of new reports highlight how fossil fuel companies have dodged responsibility for their role in the destruction and hampered the state's ability to fight back by depriving it of funds.
California's fossil fuel industry deployed lobbying muscle to kill legislation that would compel polluters to pay into a fund that would help prevent disasters and aid cleanup efforts, and has taken advantage of a tax loophole to deprives the state of corporate tax revenue, thereby "putting climate and social programs in peril." In the case of the former, California's biggest fossil fuel trade group, the Western States Petroleum Association, recently launched a digital campaign that appears aimed at throwing cold water on any such legislative efforts.
According to The Guardian, the Polluters Pay Climate Cost Recovery Act of 2024 appeared on 76% of the 74 lobby filings submitted in 2024 by the oil company Chevron and the Western States Petroleum Association.
The legislation—which didn't make it out of the state senate in 2024—would, if enacted, create a recovery program forcing fossil fuel polluters to pay their "fair share of the damage caused by the sale of their products" during the period of 2000 to 2020, according to the nonprofit newsroom CalMatters.
According to The Guardian, the filings from those two firms that included this specific bill totaled over $30 million—though lobbying laws do not require a breakdown that would make clear how much was spent specifically on the "polluter pay" law.
With Los Angeles burning, there's renewed interest in passing the bill, The Guardian reports, citing supporters of the legislation. But Western States Petroleum Association isn't sitting idly by. On January 8, the group launched ads that suggest measures like the "polluter pay" bill would force them to increase oil prices. The ads, which appear to have been taken down, do "not specifically mention the polluter pay bill, it echoes the 2024 campaign that did," wrote The Guardian.
"Accountability is an existential threat to their business model, and their business model is an existential threat to all of us, and that’s the bottom line," said Meghan Sahli-Wells, the former mayor of Culver City who currently works for the environmental advocacy group Elected Officials To Protect America, told the paper.
Meanwhile, another report from The Climate Center—a think tank and "do-tank" focused on curbing pollution—has thrust a tax loophole long used by multinational oil and gas companies, into the spotlight.
The report released last week details how "years of litigation and lobbying by oil and gas majors like ExxonMobil, Chevron, and Shell Oil" are responsible for a large corporate tax avoidance policy that is known as the "Water's Edge election" that became law in 1986.
The law allows multinational corporations to "elect" avoid taxes on earnings they designate as beyond the "water's edge" of the borders of states in which they operate, according to The Climate Center.
"Closing the loophole as it applies to the oil and gas industry could put anywhere between $75 to $146 million per year back into the state’s budget," the report states.
For context, California closed a $46 billion budget shortfall last year, including by enacting cuts to climate and clean air programs.
"The water's edge tax loophole allows multinational fossil fuel corporations to dodge paying their fair share of taxes that can help fund vital environmental projects, which could include wildfire preparedness," California Assemblymember Damon Connolly (D-12) told the progressive outlet The Lever, the first outlet to report on the findings.
California lawmakers last year passed a bill that took aim at some aspects of the loophole, but an advocacy group whose board of directors includes representative from the oil and gas industry has filed lawsuit challenging the constitutionality of the reform, according to the The Climate Center.
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Pass Wyden’s Billionaire Income Tax Bill to Close Unfair Loopholes
The bill would end two of the ultra rich’s favorite tax-avoidance strategies: “Buy-Borrow-Die” and “Buy-Hold for Decades-Sell.”
Jan 06, 2025
America’s ultra-rich today love to play tax-avoidance games. One of their favorites goes by the tag “buy-borrow-die,” a neat set of tricks that lets billionaire households avoid any taxes on the gains they make from their investments.
The simple rules of the buy-borrow-die game: buy an asset—with your millions or billions—and watch it grow. If you have a hankering to pocket some of that gain, don’t sell the asset. Any sale would trigger a capital gains tax. Just borrow against that asset instead, a simple move that lets you avoid capital gains levies so long as you live.
And what happens when you die? Nothing! Your asset’s untaxed gains vanish for income tax purposes under a tax code provision known as “stepped-up basis.”
Thanks to this buy-hold for decades-sell, the effective tax rate on the multi-billion dollar gains of America’s Bezoses, Gateses, and Buffetts, even when they do sell assets before they die, approaches zero.
This buy-borrow-die, progressive lawmakers like U.S. Sen. Ron Wyden from Oregon believe, amounts to a game plan for creating dynastic fortunes. Wyden has proposed an antidote, dubbed the “Billionaires Income Tax,” which would require billionaires to pay tax annually on the gains they make from tradable assets like the corporate shares that list on stock exchanges.
Gains from non-tradable assets would go untaxed, under Wyden’s proposal, but only until the assets get sold, at which point the tax rate would be increased to account for the tax-free compounding of annual gains. And those who inherit millions and billions from billionaires would no longer, under Wyden’s bill, be able to benefit from our current tax code’s magical stepped-up basis.
Closing the buy-borrow-die loophole would, all by itself, be reason enough for passing Wyden’s Billionaires Income Tax bill. But buy-borrow-die may only be the second leakiest loophole Wyden’s proposal would close. His Billionaires Income Tax proposal would also shut down a far less well-known loophole I like to call “Buy-Hold for Decades-Sell.”
How does this loophole work? Consider two rich taxpayers, Jack and Jill. Each invests $10 million in a stock they hope will grow at a 10% annual long-term rate, a good but not great return for a rich investor. Investors in Berkshire Hathaway, for example, have seen average annual returns of about 20%.
Our Jack goes on to hold his stock for 30 years and realizes exactly the 10% annual return he hoped to achieve.
Jill opts for a more aggressive investment strategy. After holding her stock for just over one-year, long enough to qualify her profits for the preferential tax rate available to long-term capital gains, Jill then sells at an 11% gain, pays tax on the gain, and invests the remaining proceeds in a stock she believes has more potential going forward. She successfully repeats this strategy each year for 30 years.
You might guess that Jill’s eventual nest egg at the end of 30 years, after paying federal income tax at the current long-term gains rate of 23.8%, would be larger than Jack’s. But, despite Jill’s superior investment acumen, Jack’s $135 million nest egg turns out to be 20% larger than Jill’s $112 million nest egg.
How could that be? Jack, to be sure, does pay the same 23.8% tax on his capital gain as Jill. But Jack’s money has had the benefit of 30 years of compounding before Jack has to pay that tax. That benefit far outweighs Jack’s lower annual investment return.
Jack’s whopping tax benefit from holding an appreciating asset for several decades should give us pause. After all, we want investors to seek the highest yielding investments, not the ones that get the best tax treatment. We don’t want developers of promising new technologies, for example, struggling to raise capital because our tax law confers higher returns on investors who just keep on holding old, under-performing investments.
In our example, Jill’s annual tax of 23.8% on her gains reduces Jill’s 11% pre-tax rate of return to an after-tax return of 8.38%. But Jack, because he gets to defer the tax on his 10% annual gains for 30 years, sees the after-tax return on his investment reduced by only 0.93 percentage points, to 9.07%.
As a result, Jack, a poorer investor than Jill, has millions more wealth on hand at the end of 30 years.
What tax rate would Jack have to pay annually on the growth in his stock value to place him in the same position at the end of 30 years as a one-time tax of 23.8% upon the sale of that stock? He’d only have to pay tax at a 9.3% annual rate. That 9.3% would actually run lower than the 10% income tax rate that our federal tax code currently expects Americans with incomes barely above the poverty level to pay.
In some extreme cases today, our super rich can enjoy an effective annual tax rate on their investments far lower than Jack’s.
Consider a lucky Berkshire Hathaway investor who bought 100 shares back in 1979 at $260 per share, a $26,000 investment. That investor’s shares would be worth about $70 million today. The annual pre-tax return on those shares would be 19.19%. If the investor sold the shares and paid tax at 23.8% on the long-term gain, the investor would be left with about $53.35 million.
The investor’s annual rate of return after-tax would be 18.47%, a trifling 0.72 percentage point reduction from this investor’s pre-tax rate of return. The effective annual rate of tax on the growth in the investor’s stock value would be 3.75%, less than one-sixth the 23.8% one-time rate on the investor’s compounded gains.
That about sums up perfectly the magic of buy-hold for decades-sell, the loophole that causes the effective annual tax rate on the growth in the value of investments to decline as the rate of return and length of holding period increase. Thanks to this buy-hold for decades-sell, the effective tax rate on the multi-billion dollar gains of America’s Bezoses, Gateses, and Buffetts, even when they do sell assets before they die, approaches zero.
We don’t need to just close the buy-borrow-die loophole. We desperately need to shut the buy-hold for decades-sell loophole just as firmly.
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