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capital gains tax
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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For Wall Street-Fueled Philanthropy Industry, Every Day Is Giving Tuesday
"The financial industry aggressively markets DAFs for uncharitable reasons: advantages as tax avoidance vehicles, especially for complex assets; no payout requirements—and secrecy to donors and grantees alike," said one of the report's authors.
Dec 03, 2024
A new report released on this year's philanthropic holiday known as Giving Tuesday details how the "profit motives of the financial services sector have increasingly and disastrously warped how charitable giving functions."
The analysis by the Institute for Policy Studies—titled "Gilded Giving 2024: Saving Philanthropy from Wall Street"—shows how donor-advised funds (DAFs) increasingly serve the economic interests of donors and the Wall Street firms that manage the funds, rather than the interests of nonprofit charities.
Rather than donate to a cause directly, wealthy people have the option to donate to foundations or DAFs, which can be sponsored by for-profit wealth management firms like Fidelity Investments or Charles Schwab. Firms like Fidelity Investments, in turn, benefit from being able to offer this type of service to wealthy clients.
"At last count," according to the report's authors, "DAFs and foundations together take in 35 percent of all individual giving in the U.S." If they continue to grow at the rate they have for the past five years, they're expected to take in half of all individual giving in the country by 2028.
Why is this a problem? For one thing, according to the report, some of the money that's intended for donation is scraped up by the DAFs and foundations, meaning that dollars meant for a cause are diverted elsewhere.
"With each passing year, an additional 2 cents of each dollar donated by individuals is funneled into intermediaries and away from working charities. Assuming that their assets will grow at the same rate they have over the past five years, the assets held in DAFs and foundations will eclipse $2 trillion by 2026," according to the report's authors.
What's more, there is no requirement that DAFs disburse their assets, according to the report's authors—meaning there's no guarantee the money is given to charity, and in practice the money in these accounts tends to move slowly, often generating gains instead of being dispersed.
DAFs also facilitate anonymous giving, because donations from them need only be credited to their sponsors, not the original person directing the contribution, according to Inequality.org, a project of IPS.
The report's authors argue that DAFs are part of a wider “wealth defense industry” — tax lawyers, accountants, and wealth managers whose interests are more geared towards helping their clients increase assets, minimize taxes, maximize wealth transfer to descendants, and net some of those assets for themselves in the form of fees, as opposed to supporting charitable causes.
DAFS are used strategically in this way, for example, by giving donors the ability to dispose of noncash assets, according to the report. In practice, this means that DAF donors can give stocks, real estate and other noncash assets directly to DAFS when markets are doing well, meaning they are able to get income tax deductions from their contribution while side stepping paying capital gains tax on appreciation of those assets.
"The financial industry aggressively markets DAFs for uncharitable reasons: advantages as tax avoidance vehicles, especially for complex assets; no payout requirements—and secrecy to donors and grantees alike," said Chuck Collins, co-author of the report and director of the Charity Reform Initiative at IPS.
Other key insights from the study include:
- Tech companies are offering DAF-related platforms, apps, and widgets in order to make DAF granting, and by extension charitable giving, more "frictionless." Yet, these companies, also promote DAFs to advisors and donors in terms of tax efficiency and their ability to help investment advisors "maintain AUM"—or assets under management.
- That the financial industry is "blurr[ing] the distinction between investment and philanthropy." Investors will talk about philanthropy as part of a wider portfolio of financial behaviors, as opposed to something fundamentally different—"something that, by its nature, requires individuals to relinquish personal interest and control."
The report recommends a number of reforms in order to take back philanthropy from Wall Street, including enacting regulations that would ensure donations reach working charities on reasonable timelines, undertaking {agreement} reforms to eliminate "shell games and tax dodges that financial advisors craft to diminish and delay the flow of funds to qualified charities," organizing a coalition of interested partners that would apply pressure on Congress and state governments to take action, and uplifting good examples of DAF sponsors who facilitate steady and generous giving despite gaps in the law.
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We Need an Anti-Billionaire Party
The way back for the Democratic Party begins with rejecting billionaires and their money.
Nov 16, 2024
Everything feels different this time. In November 2016, there were protests; today, mostly silence. In November 2016, there was a lot of talk about resistance; today, people are talking about stepping away from politics. In November 2016, people clamored for news; today, folks are logging off. In November 2016, there was shock. It has been replaced by numbness. But best to take the words of Joni Mitchell to heart, that “something’s lost but something’s gained, by living every day.”
The warning signs were hiding in plain sight, even at the Democrats’ ecstatic four-day August convention in Chicago that felt more like a warehouse rave than a political confab—a vibe-shift that sent delegates back home convinced that their nominee Kamala Harris was about to vanquish Donald Trump from American political life for good.
But in an election year in which there was fury from the middle class over how much it costs to get by in today’s America, some observers—especially in the party’s left flank—were appalled at the barely hidden embrace of big money. Across the Windy City, in rented venues like the House of Blues, lobbyists for industries like crypto or PACs funded by firms like Cigna or AT&T threw posh late-night private parties for Democratic insiders after the TV lights were turned off.
The current Democratic brand is toxic—especially with working-class voters who have no idea what the party stands for. It’s past time to cast out the money-changers and stop pandering to millionaires and billionaires who may be pro-abortion rights or support the LBGTQ community, but who mainly just want to keep America’s unequal economic status quo.
But one pivotal moment inside the United Center even horrified the seen-it-all investigative journalist and former Sen. Bernie Sanders speechwriter David Sirota, who noted that a line from Illinois governor and Hilton hotel heir J.B. Pritzker—“Take it from an actual billionaire, Trump is rich in only one thing, stupidity”—caused “raucous applause from an audience overjoyed to have found its newest billionaire idol.”
Sirota and others who heard it knew instinctively that this was not a winning message for the party that once dominated American politics in the mid-20th century by turning out the working class, and Tuesday’s results proved them right. In the flaming wreckage of an election in which Trump won a return ticket to the White House by winning the popular vote for the first time in three tries, while his fellow Republicans were capturing control of Congress, both pundits and Democratic insiders have spent the last week fighting over who to blame.
For these wounded elites, prime suspects include everything from President Joe Biden’s insistence on running and staying in the race until July, to Harris’ failure to reach young men by not going on testosterone-laden shows like Joe Rogan’s podcast, to the party’s collective inability to feel consumers’ pain over the post-COVID spike in prices. But you don’t need to be a rocket scientist or even a political scientist to argue that the biggest blunder was not attacking the billionaire class because Harris was too busy begging for their campaign checks.
If there is one thing that gets working-class Americans across the familiar fault lines of political ideology or race or ethnicity to agree, it’s that the super rich have too much wealth and power and don’t pay their fair share. In March, a Bloomberg News/Morning Consult poll of voters in the seven key swing states found some 69% of voters—including 58% of Republicans and 66% of independents—supported higher taxes on billionaires. That populist fervor is hardly surprising in a nation where the top 10% controls 60% of all wealth, while the bottom half struggles with just 6%.
But while the Harris campaign did pay lip service to raising taxes on the super wealthy, it didn’t give voters the red meat of a soak-the-rich campaign that might have landed emotionally in a nation that most voters believe is on the wrong track. That’s probably because Team Harris, with its ambitious yet eventually reached goal of raising $1 billion in order to outspend Trump on TV ads and getting out the vote, felt it needed to woo Big Business, not offend it with a truly populist campaign.
A New York Times post-mortem on what went wrong with the vice president’s messaging and proposals noted in its headline that she had a “Wall Street-Approved Economic Pitch” that “Fell Flat” with voters, writing that Harris “adopted marginal pro-business tweaks to the status quo that both her corporate and progressive allies agreed never coalesced into a clear economic argument.”
It was arguably worse than that. One of the Democrat’s few firm economic proposals was a 28% capital-gains tax plan that was actually lower and thus more friendly to the wealthy than what Biden had been proposing. Much of her economic agenda, according to the Times, was bounced off a key adviser: her brother-in-law Tony West, a corporate lobbyist for Uber—and it showed. Although the Biden administration had been cracking down on abuses in cryptocurrency, Harris signaled support for the scam-plagued, polluting industry, and won over some new donors.
Harris even campaigned with a billionaire—the colorful Dallas Mavericks owner Mark Cuban—who went before a Wisconsin rally to say the Democrat “has an amazing plan for small business,” even after he’d initially lobbied for Harris to dump controversial tough-on-business Federal Trade Commission chief Lina Khan. Watching Harris’ carefully calibrated campaign, it’s also hard not to wonder whether her tepid talk about reining in fossil fuels and even her weak-tea echo of Biden’s Gaza policies—unpopular with many young voters—were meant more for donors than for voters.
It can’t be a coincidence that Democrats’ decades-long embrace of the donor class in an era of big-money politics has disabled its potential populist message to working folks who elected FDR, JFK and Bill Clinton. The Democrats need radical change in a hurry if the party wants to retake the House in the 2026 midterms and start the search for a new leader who can replace Trump in the 2028 election—assuming that we’re still having those by then.
That won’t happen under the current Democratic leadership or its consultants, who owe their status to the party’s wealthiest supporters. Any serious political movement to reinvent the anti-MAGA left will have to start from the bottom-up—with meetings and phone calls and rallies by community activists and environmentalists and ministers and everyday folks. The goal must be finding a new breed of candidates who will reject all billionaire and corporate contributions. That can help remake Congress and eventually boost a presidential candidate truly committed to taxing the rich, waging a new war on poverty, cutting the wasteful Pentagon budget and expanding the Supreme Court to protect these gains.
Sound crazy? Such a movement happened in this century, when the Tea Party emerged in 2009-10 to challenge established Republicans with new grassroots organizations that met regularly, staged boisterous protests and primaried GOP incumbents, pushing their party furtherto the right. That short-lived counter-revolution set the stage for Trump, and for last week’s big victory.
The current Democratic brand is toxic—especially with working-class voters who have no idea what the party stands for. It’s past time to cast out the money-changers and stop pandering to millionaires and billionaires who may be pro-abortion rights or support the LBGTQ community, but who mainly just want to keep America’s unequal economic status quo. Build a new Democratic Party that bans big money, because elections are won with votes, not dollars. The next Democrat who brags about how obscenely rich he is should be booed out of the arena.
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