“corporate governance services” to investment managers.

For $15,000 a year, plus other fees, HighWater would provide an employee to sit on the board of the financial vehicle that the fund manager was expected to launch to accept the wealthy family’s money, according to emails between the fund manager and a HighWater executive reviewed by The New York Times.

The fund manager also brought on Boris Onefater, who ran a small U.S. consulting firm, Constellation, as another board member. Mr. Onefater said in an interview that he couldn’t remember whose money the Cayman vehicle was managing. “You’re asking for ancient history,” he said. “I don’t recall Mr. Abramovich’s name coming up.”

The fund manager hired Mourant, an offshore law firm, to get the paperwork for the Cayman vehicle in order. The managing partner of Mourant did not respond to requests for comment.

He also hired GlobeOp Financial Services, which provides administration services to hedge funds, to ensure that the Cayman entity was complying with anti-money-laundering laws and wasn’t doing business with anyone who had been placed under U.S. government sanctions, according to a copy of the contract.

“We abide by all laws in all jurisdictions in which we do business,” said Emma Lowrey, a spokeswoman for SS&C Technologies, a financial technology company based in Windsor, Conn., that now owns GlobeOp.

John Lewis, a HighWater executive, said in an email to The Times that his firm received four referrals from Concord from 2011 to 2014 and hadn’t dealt with the firm since then.

“We were aware of no links to Russian money or Roman Abramovich,” Mr. Lewis said. He added that GlobeOp “did not identify anything unusual, high risk, or that there were any politically exposed persons with respect to any investors.”

The Cayman fund opened for business in July 2012 when $20 million arrived by wire transfer. The expectation was that tens of millions more would follow, although additional funds never showed up. The Cayman fund was run as an independent entity, using the same investment strategy — buying and selling exchange-traded funds — employed by the fund manager’s main U.S. hedge fund.

The $20 million was wired from an entity called Caythorpe Holdings, which was registered in the British Virgin Islands.

Documents accompanying the wire transfer showed that the money originated with Kathrein Privatbank in Vienna. It arrived in Grand Cayman after passing through another Austrian bank, Raiffeisen, and then JPMorgan. (JPMorgan was serving as a correspondent bank, essentially acting as an intermediary for banks with smaller international networks.)

A spokesman for Kathrein declined to comment. A spokeswoman for JPMorgan declined to comment. Representatives for Raiffeisen did not respond to requests for comment.

The fund manager noticed that some of the documentation was signed by a lawyer named Natalia Bychenkova. The Russian-sounding name led him to conclude that he was probably managing money for a Russian oligarch. But the fund manager wasn’t bothered, since GlobeOp had verified that Caythorpe was compliant with know-your-customer and anti-money-laundering rules and laws.

He didn’t know who controlled Caythorpe, and he didn’t ask.

In early 2014, after Russia invaded the Ukrainian region of Crimea, markets tanked. The fund manager made a bearish bet on the direction of the stock market, and his fund got crushed when stocks rallied.

The next year, Caythorpe withdrew its money from the Cayman fund. Caythorpe was liquidated in 2017.

The fund manager said he didn’t realize until this month that he had been investing money for Mr. Abramovich.

Susan C. Beachy and Kitty Bennett contributed research. Maureen Farrell contributed reporting.

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How to Fight Inflation With Lessons From History

Annual spending in the Union reached a staggering 16 times its prewar budget. Despite the need for funds, there was great fear in Congress of increasing taxes because of Americans’ well-known antipathy to taxation.

But Salmon P. Chase, the fiscally conservative Treasury secretary, was mortally afraid of inflation. He recognized that without revenue the government would have to resort to the printing press. After the southern states seceded, interest rates on the country’s debt soared and foreigners refused to lend.

Thaddeus Stevens, the chair of the House Ways and Means Committee, went further than Mr. Chase imagined by inventing an entirely new tax code. Previously, the Union had funded itself with tariffs on foreign trade, which it raised several times. Alongside that it created a system of “internal taxes,” on everything from personal income to leaf tobacco, liquor, slaughtered hogs and fees on auctioneers. Congress also created a new bureau to collect taxes, a forerunner of the Internal Revenue Service, underscoring its commitment to raising revenue this way.

Mr. Stevens had no idea how much revenue the taxes would raise, or if people would even pay them. (“Everything on the earth and under the earth is to be taxed,” one Ohioan groused.) But by 1865, the Treasury netted $300 million from customs and internal taxes — six times its prewar tax revenue.

That revenue helped moderate the inflation created by the issuance of “greenbacks,” notes that circulated as money, to pay for the war. The country’s credit improved and Mr. Chase was able to borrow prodigious sums. Ultimately, inflation in the Union was no greater than during the two World Wars in the following century.

The Confederacy faced similar financial challenges. Christopher Memminger, its German-born Treasury secretary, warned that printing notes was “the most dangerous of all methods of raising money.” But the South was ideologically opposed to taxation, especially by the central government.

The South approved a very modest tax (half a percent on real estate), but collection was left to the states and few tried to collect it. With cotton shipments to Europe pinched by the Union blockade, Mr. Memminger soon found he had little choice but to print notes to cover the cost of the war. These inflated at a catastrophic rate.

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Biden Finds Raising Corporate Tax Rates Easier Abroad Than at Home

ROME — President Biden and other world leaders endorsed a landmark global agreement on Saturday that seeks to block large corporations from shifting profits and jobs across borders to avoid taxes, a showcase win for a president who has found raising corporate tax rates an easier sell with other countries than with his own party in Congress.

The announcement in the opening session of the Group of 20 summit marked the world’s most aggressive attempt yet to stop opportunistic companies like Apple and Bristol Myers Squibb from sheltering profits in so-called tax havens, where tax rates are low and corporations often maintain little physical presence beyond an official headquarters.

It is a deal years in the making, which was pushed over the line by the sustained efforts of Mr. Biden’s Treasury Department, even as the president’s plans to raise taxes in the United States for new social policy and climate change programs have fallen short of his promises.

The revenue expected from the international pact is now critical to Mr. Biden’s domestic agenda, an unexpected outcome for a president who has presented himself more as a deal maker at home rather than abroad.

end the global practice of profit-shifting, celebrated the international tax provisions this week and said they would be significant steps toward Mr. Biden’s vision of a global economy where companies invest, hire and book more profits in the United States.

But they also conceded that infighting among congressional Democrats had left Mr. Biden short of fulfilling his promise to make corporations pay their “fair share,” disappointing those who have pushed Mr. Biden to reverse lucrative tax cuts for businesses passed under Mr. Trump.

The framework omits a wide range of corporate tax increases that Mr. Biden campaigned on and pushed relentlessly in the first months of his presidency. He could not persuade 50 Senate Democrats to raise the corporate income tax rate to 28 percent from 21 percent, or even to a compromise 25 percent, or to eliminate incentives that allow some large firms — like fossil fuel producers — to reduce their tax bills.

“It’s a tiny, tiny, tiny, tiny, step,” Erica Payne, the president of a group called Patriotic Millionaires that has urged tax increases on corporations and the wealthy, said in a statement after Mr. Biden’s framework announcement on Friday. “But it’s a step.”

The Treasury Department said on Friday that even the additional enforcement money for the I.R.S. could still generate $400 billion in additional tax revenue over 10 years and said that was a “conservative” estimate.

An administration official said that the difficulty in rolling back the Trump tax cuts was the result of the fact that the Democrats are a big tent party ideologically with a very narrow majority in Congress, where a handful of moderates currently rule.

In Rome, Mr. Biden’s struggle to raise taxes more has not complicated the sealing of the international agreement. The move by the heads of state to commit to putting the deal in place by 2023 looms as the featured achievement of the summit, and Mr. Biden’s surest victory of a European swing that also includes a climate conference in Scotland next week.

Briefing reporters on Friday evening, a senior administration official, speaking on the condition of anonymity in order to preview the first day of the summit, said Biden aides were confident that world leaders were sophisticated and understood the nuances of American politics, including the challenges in passing Mr. Biden’s tax plans in Congress.

The official also said world leaders see the tax deal as reshaping the rules of the global economy.

The international tax agreement represented a significant achievement of economic diplomacy for Mr. Biden and Ms. Yellen, who dedicated much of her first year on the job to reviving negotiations that stalled during the Trump administration. To show that the United States was serious about a deal, she abandoned a provision that would have made it optional for American companies to pay new taxes to foreign countries and backed away from an initial demand for a global minimum tax of 21 percent.

For months, Ms. Yellen cajoled Ireland’s finance minister, Paschal Donohoe, to back the agreement, which would require Ireland to raise its 12.5 percent corporate tax rate — the centerpiece of its economic model to attract foreign investment. Ultimately, through a mix of pressure and pep talks, Ireland relented, removing a final obstacle that could have prevented the European Union from ratifying the agreement.

Some progressives in the United States say that Mr. Biden’s ability to follow through on his end of the bargain was a crucial piece of the framework spending bill.

“The international corporate reforms are the most important,” said Seth Hanlon, a senior fellow at the liberal Center for American Progress, who specializes in tax policy, “because they are linked to the broader multilateral effort to stop the corporate race to the bottom. It’s so important for Congress to act this year to give that effort momentum.”

Jim Tankersley reported from Rome, and Alan Rappeport from Washington.

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How Top Accounting Firms Help Their Clients Sidestep Taxes

This year, Mr. Harter returned to PwC.

“I fully complied with Treasury Department conflicts rules by not meeting with PwC representatives” during a two-year “cooling off” period that restricts government officials from meeting with their former employers, Mr. Harter said. Although he was involved in the construction of the offshore tax break and met with corporate lobbyists, Mr. Harter said he did not recall meeting with Ms. Olson or other PwC officials on the topic.

Ms. Olson referred questions to PwC.

The 2017 tax overhaul included a provision that let some people take a 20 percent tax deduction on certain types of business income. But the law — known as Section 199A — largely excluded an undefined category of “brokerage services.” In 2018, lobbyists for several industries, including real estate and insurance, visited the Treasury to try to persuade officials that the broker prohibition should not apply to them.

On Aug. 1, records show, Ms. Ellis met with her former PwC colleague, Mr. Feuerstein, and three other lobbyists for his client, the National Association of Realtors. They wanted real estate brokers to qualify for the 20 percent deduction.

The meeting took place before the first draft of the proposed rules was even made public, which meant that, right off the bat, Ms. Ellis’s former PwC colleague and his client had an inside track.

When the Treasury published its first version of the proposed rules a week later, real estate brokers were eligible. The National Association of Realtors took credit for the victory on its website. (The final rules applied only to brokers of stocks and other securities.)

Ms. Ellis’s meeting with Mr. Feuerstein appeared to violate a federal ethics rule that restricts government officials from meeting with their former private sector colleagues, said Don Fox, the acting director of the Office of Government Ethics during the Obama administration and, before that, a lawyer in Republican and Democratic administrations.

Mr. Fox described the meeting as improper. “It certainly is going to call into question how that regulation was drafted,” he said. “There’s no way to undo the taint that is now going to be attached to that.”

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Hedge Fund’s Insiders Agree to Pay as Much as $7 Billion to I.R.S.

A yearslong dispute between a pioneering hedge fund and the Internal Revenue Service ended Thursday with an enormous bill for taxes and penalties: as much as $7 billion.

James Simons, a mathematician whose algorithmic approach has been adopted by many other investment funds, and some of his former colleagues at Renaissance Technologies have settled a decade-long dispute with the government over the tax treatment of some of their investments, the firm said in letter to investors.

The settlement, which involves 10 years’ worth of trades made by the hedge fund, could be worth as much as $7 billion, according to a person with knowledge of the agreement. It is one of the largest federal tax disputes in history.

The deal ends a standoff that led to a congressional investigation and involved two politically connected financiers: Mr. Simons, a longtime patron of Democratic candidates with an estimated net worth of $25 billion, and Robert Mercer, a former Renaissance executive whose advocacy for conservative causes included helping to found Cambridge Analytica. After Donald J. Trump won the 2016 presidential election, the now-defunct political consulting firm became embroiled in a scandal for harvesting Facebook data without users’ consent to assist his campaign.

$10 million in Breitbart News, and was a key supporter of Stephen K. Bannon, who was Breitbart’s chairman before becoming Mr. Trump’s chief strategist.

The billions in payments to the I.R.S. will be made by current and former investors in a small group of Renaissance funds, but principally its Medallion fund. Those investors include seven people who were members of the firm’s board between 2005 and 2015, as well as their spouses. Mr. Simons will make a payment of $670 million on top of his obligation as part of that group, according to the letter.

“Renaissance’s board ultimately concluded that the interests of our investors from the relevant period would be best served by agreeing to this resolution with the I.R.S., rather than risking a worse outcome, including harsher terms and penalties, that could result from litigation,” Peter Brown, the firm’s chief executive, wrote.

Renaissance is best known for pioneering a data-intensive form of stock trading called quantitative strategy, which has been adopted by many other hedge funds and trading platforms on Wall Street. The settlement centers on the firm’s Medallion fund, which manages about $15 billion, mostly for employees and former employees of the firm and their family members.

Mr. Simons founded the firm in 1982. Once the head of the math department at Stony Brook University on Long Island, he was a code-breaker for the U.S. military during the Vietnam War. He stepped down from the firm’s day-to-day operations in 2010, handing the reins to Mr. Mercer and Mr. Brown as co-chief executives.

reported that contractors and employees of Cambridge Analytica, eager to sell psychological profiles of American voters to political campaigns, acquired the private Facebook data of tens of millions of users — the largest known leak in the company’s history. Facebook eventually said as many as 87 million users — mostly in the United States — had their data harvested by the firm.

Mr. Mercer’s decision to resign as co-chief of Renaissance shortly after Mr. Trump won the presidency came about in part because of his involvement in bankrolling Cambridge Analytica. Some of the hedge fund’s investors had voiced concerns about Mr. Mercer’s political activities.

The firm’s letter on Thursday said that aside from the board members and their spouses, other investors will be required to pay additional tax and interest owed, but no penalties. Renaissance’s outside clients, who include wealthy individuals, pensions and other investors, are not expected to be affected by the settlement.

The tax dispute involved Medallion’s fast-paced options trading and how those transactions should be taxed — a major consideration given that the firm’s rapid-fire trading had a history of generating big profits.

At the time of the transactions the federal tax rate on long-term capital gains was about half what it was for short-term capital gains. The hedge fund argued that many of its trades were eligible to be taxed at the lower rate because it had converted those options trades into longer-term holdings through the use of complex financial instruments.

These instruments involved baskets of stocks put together by a bank. But Medallion didn’t buy the actual basket of stocks; it instead bought an option on that basket and sometimes gave the banks instructions on how to trade those stocks. Basket options have been criticized for having allowed hedge funds to borrow money more easily and allowing them to make bigger and potentially riskier trades.

The I.R.S. argued that the basket option trades should have been taxed at the higher rate because they were mainly the result of short-term trading.

The disagreement drew the attention of Congress, and led to rule changes. Following a report from the Senate Permanent Committee on Investigations, the I.R.S. issued new guidance in 2015 that sought to clamp down on this type of trading by making it more difficult and costly for hedge funds to buy basket options. Such investment vehicles had to be declared on the tax returns of any investor who used them, the agency said.

The I.R.S. had said its guidance on basket options would be retroactive, and applied to all transactions as far back as Jan. 1, 2011.

Still, some senators were critical of the I.R.S. for taking so long to change its rules and start investigating the trading practice, including at Renaissance.

Senator Carl Levin, the Michigan Democrat who headed the Senate committee in 2014 and died in July, said the I.R.S. guidance would stop banks and hedge funds from using “dubious structured financial products” that had cost taxpayers billions.

Elise Bean, a former aide to Mr. Levin, said she wished her former boss had lived to see the settlement. “It’s good to see that, despite a yearslong, knock-down, bare-knuckles battle, the I.R.S. prevailed in compelling at least one set of billionaires to pay the taxes they owe,” she said.

Jesse Drucker contributed reporting.

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Child Tax Credit Payments Have Begun. Should You Opt Out?

“The advance of the credit reduces the total amount of taxes paid,” said Rob Seltzer, an accountant in Los Angeles. “So there could be a problem with an estimated tax penalty,” depending on how much the taxpayer earns this year compared with last. It may make sense to run a tax projection with a professional to see if it makes sense to opt out.

You need to live in the United States for more than half of 2021 to be eligible for the advanced payments, but expatriate taxpayers can still claim the expanded credit on their return, according to the I.R.S. (The refundable portion of the credit, however, will be curtailed to the prior $1,400 limit.) Military members stationed abroad are still eligible for the advanced payments.

Some households are simply accustomed to getting a large refund when they file, using it as a forced savings plan. If you have come to depend on a big refund, you can opt out of all future payments and receive the full value of the credit when you file your return next year.

“Opting out or making changes to the payment comes down to personal preference of when and how you want to receive the money,” said Andy Phillips, the director of the Tax Institute at H&R Block. “If you prefer monthly payments of smaller amounts, no need to make changes.”

Sheila Taylor-Clark, a certified public accountant and secretary of the National Society of Black C.P.A.s, has practical advice for clients who don’t necessarily want to opt out but who may be uncertain on where they stand: “Drop that money into an interest-bearing account, so if you owe money you can just send that back next April,” she said.

To opt out of receiving the payments, taxpayers should visit the Child Tax Credit Update Portal. If you don’t already have an account, you’ll need to create one. And if you’re married and file a joint return, both spouses will need to create accounts and opt out; spouses who don’t opt out will continue to receive half of the advance monthly payment.

Besides stopping the checks, the portal can be used to check the status of your payments; change the bank account receiving them; or to switch your payments to direct deposit from paper checks.

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How Private Equity Firms Avoid Taxes

There were two weeks left in the Trump administration when the Treasury Department handed down a set of rules governing an obscure corner of the tax code.

Overseen by a senior Treasury official whose previous job involved helping the wealthy avoid taxes, the new regulations represented a major victory for private equity firms. They ensured that executives in the $4.5 trillion industry, whose leaders often measure their yearly pay in eight or nine figures, could avoid paying hundreds of millions in taxes.

The rules were approved on Jan. 5, the day before the riot at the U.S. Capitol. Hardly anyone noticed.

The Trump administration’s farewell gift to the buyout industry was part of a pattern that has spanned Republican and Democratic presidencies and Congresses: Private equity has conquered the American tax system.

one recent estimate, the United States loses $75 billion a year from investors in partnerships failing to report their income accurately — at least some of which would probably be recovered if the I.R.S. conducted more audits. That’s enough to roughly double annual federal spending on education.

It is also a dramatic understatement of the true cost. It doesn’t include the ever-changing array of maneuvers — often skating the edge of the law — that private equity firms have devised to help their managers avoid income taxes on the roughly $120 billion the industry pays its executives each year.

Private equity’s ability to vanquish the I.R.S., Treasury and Congress goes a long way toward explaining the deep inequities in the U.S. tax system. When it comes to bankrolling the federal government, the richest of America’s rich — many of them hailing from the private equity industry — play by an entirely different set of rules than everyone else.

The result is that men like Blackstone Group’s chief executive, Stephen A. Schwarzman, who earned more than $610 million last year, can pay federal taxes at rates similar to the average American.

Lawmakers have periodically tried to force private equity to pay more, and the Biden administration has proposed a series of reforms, including enlarging the I.R.S.’s enforcement budget and closing loopholes. The push for reform gained new momentum after ProPublica’s recent revelation that some of America’s richest men paid little or no federal taxes.

nearly $600 million in campaign contributions over the last decade, has repeatedly derailed past efforts to increase its tax burden.

Taylor Swift’s back music catalog.

The industry makes money in two main ways. Firms typically charge their investors a management fee of 2 percent of their assets. And they keep 20 percent of future profits that their investments generate.

That slice of future profits is known as “carried interest.” The term dates at least to the Renaissance. Italian ship captains were compensated in part with an interest in whatever profits were realized on the cargo they carried.

The I.R.S. has long allowed the industry to treat the money it makes from carried interests as capital gains, rather than as ordinary income.

article highlighting the inequity of the tax treatment. It prompted lawmakers from both parties to try to close the so-called carried interest loophole. The on-again, off-again campaign has continued ever since.

Whenever legislation gathers momentum, the private equity industry — joined by real estate, venture capital and other sectors that rely on partnerships — has pumped up campaign contributions and dispatched top executives to Capitol Hill. One bill after another has died, generally without a vote.

One day in 2011, Gregg Polsky, then a professor of tax law at the University of North Carolina, received an out-of-the-blue email. It was from a lawyer for a former private equity executive. The executive had filed a whistle-blower claim with the I.R.S. alleging that their old firm was using illegal tactics to avoid taxes.

The whistle-blower wanted Mr. Polsky’s advice.

Mr. Polsky had previously served as the I.R.S.’s “professor in residence,” and in that role he had developed an expertise in how private equity firms’ vast profits were taxed. Back in academia, he had published a research paper detailing a little-known but pervasive industry tax-dodging technique.

$89 billion in private equity assets — as being “abusive” and a “thinly disguised way of paying the management company its quarterly paycheck.”

Apollo said in a statement that the company stopped using fee waivers in 2012 and is “not aware of any I.R.S. inquiries involving the firm’s use of fee waivers.”

floated the idea of cracking down on carried interest.

Private equity firms mobilized. Blackstone’s lobbying spending increased by nearly a third that year, to $8.5 million. (Matt Anderson, a Blackstone spokesman, said the company’s senior executives “are among the largest individual taxpayers in the country.” He wouldn’t disclose Mr. Schwarzman’s tax rate but said the firm never used fee waivers.)

Lawmakers got cold feet. The initiative fizzled.

In 2015, the Obama administration took a more modest approach. The Treasury Department issued regulations that barred certain types of especially aggressive fee waivers.

But by spelling that out, the new rules codified the legitimacy of fee waivers in general, which until that point many experts had viewed as abusive on their face.

So did his predecessor in the Obama administration, Timothy F. Geithner.

Inside the I.R.S. — which lost about one-third of its agents and officers from 2008 to 2018 — many viewed private equity’s webs of interlocking partnerships as designed to befuddle auditors and dodge taxes.

One I.R.S. agent complained that “income is pushed down so many tiers, you are never able to find out where the real problems or duplication of deductions exist,” according to a U.S. Government Accountability Office investigation of partnerships in 2014. Another agent said the purpose of large partnerships seemed to be making “it difficult to identify income sources and tax shelters.”

The Times reviewed 10 years of annual reports filed by the five largest publicly traded private equity firms. They contained no trace of the firms ever having to pay the I.R.S. extra money, and they referred to only minor audits that they said were unlikely to affect their finances.

Current and former I.R.S. officials said in interviews that such audits generally involved issues like firms’ accounting for travel costs, rather than major reckonings over their taxable profits. The officials said they were unaware of any recent significant audits of private equity firms.

For a while, it looked as if there would be an exception to this general rule: the I.R.S.’s reviews of the fee waivers spurred by the whistle-blower claims. But it soon became clear that the effort lacked teeth.

Kat Gregor, a tax lawyer at the law firm Ropes & Gray, said the I.R.S. had challenged fee waivers used by four of her clients, whom she wouldn’t identify. The auditors struck her as untrained in the thicket of tax laws governing partnerships.

“It’s the equivalent of picking someone who was used to conducting an interview in English and tell them to go do it in Spanish,” Ms. Gregor said.

The audits of her clients wrapped up in late 2019. None owed any money.

As a presidential candidate, Mr. Trump vowed to “eliminate the carried interest deduction, well-known deduction, and other special-interest loopholes that have been so good for Wall Street investors, and for people like me, but unfair to American workers.”

wanted to close the loophole, congressional Republicans resisted. Instead, they embraced a much milder measure: requiring private equity officials to hold their investments for at least three years before reaping preferential tax treatment on their carried interests. Steven Mnuchin, the Treasury secretary, who had previously run an investment partnership, signed off.

McKinsey, typically holds investments for more than five years. The measure, part of a $1.5 trillion package of tax cuts, was projected to generate $1 billion in revenue over a decade.

credited Mr. Mnuchin, hailing him as “an all-star.”

Mr. Fleischer, who a decade earlier had raised alarms about carried interest, said the measure “was structured by industry to appear to do something while affecting as few as possible.”

Months later, Mr. Callas joined the law and lobbying firm Steptoe & Johnson. The private equity giant Carlyle is one of his biggest clients.

It took the Treasury Department more than two years to propose rules spelling out the fine print of the 2017 law. The Treasury’s suggested language was strict. One proposal would have empowered I.R.S. auditors to more closely examine internal transactions that private equity firms might use to get around the law’s three-year holding period.

The industry, so happy with the tepid 2017 law, was up in arms over the tough rules the Treasury’s staff was now proposing. In a letter in October 2020, the American Investment Council, led by Drew Maloney, a former aide to Mr. Mnuchin, noted how private equity had invested in hundreds of companies during the coronavirus pandemic and said the Treasury’s overzealous approach would harm the industry.

The rules were the responsibility of Treasury’s top tax official, David Kautter. He previously was the national tax director at EY, formerly Ernst & Young, when the firm was marketing illegal tax shelters that led to a federal criminal investigation and a $123 million settlement. (Mr. Kautter has denied being involved with selling the shelters but has expressed regret about not speaking up about them.)

On his watch at Treasury, the rules under development began getting softer, including when it came to the three-year holding period.

Monte Jackel, a former I.R.S. attorney who worked on the original version of the proposed regulations.

Mr. Mnuchin, back in the private sector, is starting an investment fund that could benefit from his department’s weaker rules.

Even during the pandemic, the charmed march of private equity continued.

The top five publicly traded firms reported net profits last year of $8.6 billion. They paid their executives $8.3 billion. In addition to Mr. Schwarzman’s $610 million, the co-founders of KKR each made about $90 million, and Apollo’s Leon Black received $211 million, according to Equilar, an executive compensation consulting firm.

now advising clients on techniques to circumvent the three-year holding period.

The most popular is known as a “carry waiver.” It enables private equity managers to hold their carried interests for less than three years without paying higher tax rates. The technique is complicated, but it involves temporarily moving money into other investment vehicles. That provides the industry with greater flexibility to buy and sell things whenever it wants, without triggering a higher tax rate.

Private equity firms don’t broadcast this. But there are clues. In a recent presentation to a Pennsylvania retirement system by Hellman & Friedman, the California private equity giant included a string of disclaimers in small font. The last one flagged the firm’s use of carry waivers.

The Biden administration is negotiating its tax overhaul agenda with Republicans, who have aired advertisements attacking the proposal to increase the I.R.S.’s budget. The White House is already backing down from some of its most ambitious proposals.

Even if the agency’s budget were significantly expanded, veterans of the I.R.S. doubt it would make much difference when it comes to scrutinizing complex partnerships.

“If the I.R.S. started staffing up now, it would take them at least a decade to catch up,” Mr. Jackel said. “They don’t have enough I.R.S. agents with enough knowledge to know what they are looking at. They are so grossly overmatched it’s not funny.”

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How Long Should It Take to Give Away Millions?

Ms. Madoff and others pushing for change see a growing gap between reputation-burnishing promises of money and distributions to people who need it. The Giving Pledge, which was started by Bill Gates, Melinda French Gates and their friend and collaborator Warren E. Buffett, gave billionaires a space where they could announce their intention to give away half their fortunes or more, often to great acclaim. But it provides no mechanism to monitor or ensure the giving actually happens.

Earlier this year, the Chronicle of Philanthropy ranked Jeffrey P. Bezos, the founder of Amazon, as the top philanthropist of 2020 because he committed $10 billion to his Bezos Earth Fund to fight climate change. But he had handed out less than one-tenth of that, $791 million, to working nonprofits like the Environmental Defense Fund and Natural Resources Defense Council.

Charitable giving has remained relatively steady for decades, clocking in at roughly 2 percent of disposable income per year, give or take a few tenths of a percent. In 1991, the year that Fidelity began to offer donor-advised funds, just 5 percent of giving went to foundations and DAFs. By 2019, the most recent year available, that figure had risen to 28 percent.

It was January 2020 when that small group gathered at the offices of the nonprofit consulting firm the Bridgespan Group in Manhattan for a wonky brainstorming session about the state of philanthropy. The group included foundation leaders, former congressional staff members, former senior Internal Revenue Service officials and a key constituency in any effort to change how billionaires give away their money: billionaires.

One of the organizers was John D. Arnold. Once a trader at Enron, the Houston energy company that infamously collapsed in 2001, Mr. Arnold later ran his own hedge fund, which made him one of the youngest billionaires in the United States.

Ms. Madoff, another leader of the initiative, has written a book, “Immortality and the Law,” about the growing legal power of dead people in America and has applied her knowledge of estate taxes and inheritance law to the rising field of philanthropy.

The group focused on the fact that most of the laws governing philanthropy were half a century old, dating back to 1969.

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Treasury Defends Plan to Narrow Tax Gap by Hiring More I.R.S. Agents

The Biden administration on Thursday defended its assessment that it could raise $700 billion in revenue by pumping money into the Internal Revenue Service to beef up its enforcement capabilities amid criticism that its projections were overly rosy.

The Treasury Department released a 22-page report laying out the administration’s new “tax compliance agenda,” which is a centerpiece of its plans to pay for a $1.8 trillion infrastructure and jobs proposal. The Biden administration wants to give the I.R.S. $80 billion over the next decade so that it can overhaul its outdated technology and ramp up audits of wealthy taxpayers and corporations.

The Biden administration’s estimates of the return on investment that it could generate from boosting the I.R.S. budget far surpassed projections by the nonpartisan Congressional Budget Office. And John Koskinen, a former I.R.S. commissioner under President Barack Obama and President Donald J. Trump, has suggested that it would be hard for the cash-strapped agency to efficiently spend that much money.

The Treasury Department said that it believes its projections are conservative. Much of the revenue from more rigid enforcement would become evident in the later part of the decade, the report said, but Treasury officials believe that with more enforcement staff and better technology the I.R.S. can chip away at the “tax gap.”

$1 trillion owed to the government is not being collected every year. The Treasury Department estimated on Thursday that in 2019 the tax gap was $584 billion and is on pace to total $7 trillion over the next 10 years.

The Treasury report said that much of the revenue it estimates would come through its “information reporting” rules for financial institutions. This would give the I.R.S. more visibility into corporate accounts to determine how much money they are actually taking in and what should be taxed. The department said it expects that such reporting would be helpful for audits and would serve as a deterrent against corporate tax evasion.

The new information reporting rules would also include an effort by the Biden administration to bring cryptocurrencies into the tax regime and to crack down on those using cryptocurrencies to avoid paying taxes. The report said that cryptocurrency exchange accounts and payment accounts that accept them would fall under the reporting rules. Businesses that receive cryptoassets with a fair market value of more than $10,000 would be subject to information reporting.

The Biden administration has faced questions from Republican lawmakers, such as Senator Mike Crapo of Idaho, to justify its claims that giving the I.R.S. so much money will yield such robust returns. Conservative political groups have criticized the Biden administration plan to hire an army of I.R.S. agents, saying it’s a way to hike taxes.

The Treasury report attempted to rebut such claims, noting that increased audits would be focused on the rich.

“It is important to note that the President’s compliance proposals are designed to ameliorate existing inequities by focusing on high-end evasion,” the report said. “Audit rates will not rise relative to recent years for those with less than $400,000 in actual income.”

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Investors Put Millions Into a Luxury Student Dorm. They Say They Were Ripped Off.

Ms. Martinez, who lives not far from the dorm, said she had invested a little over $100,000 in the deal — money that came from the sale of a rental property. Like many investors in Skyloft, she was looking for a way to defer paying capital gains on the prior sale, and the private placement was marketed by brokers as a “1031 exchange” deal that would keep the Internal Revenue Service at bay.

A 1031 exchange deal, named after a section of the federal tax code, allows an investor to defer paying capital gains on the sale of property as long as the proceeds are invested into another property of equal or greater value to the one sold. These transactions are often criticized as a tax break for the rich, but the deals have also long attracted interest from investors of more moderate means.

The Biden administration is considering eliminating many of these deals as a way to raise additional revenue to pay for increased spending on child care and family leave programs. The Biden plan would allow 1031 exchanges to continue for most investors seeking to defer up to $500,000 in capital gains — many in the Skyloft deal fit that bill.

In recent years, student housing projects like Skyloft have become especially attractive real estate investments — especially as universities have encouraged the building of luxury apartment buildings to cater to students from wealthy families. Before the pandemic, there were, on average, $7 billion in student housing transactions in the United States each year. That was up from $3 billion just a decade ago, according to CBRE, a commercial real estate services firm.

Court filings and interviews with investors set out how the Skyloft project financing worked. To secure the $124 million purchase of Skyloft, Nelson Partners obtained a $66 million mortgage from a group of lenders led by UBS, in addition to the $75 million raised from ordinary investors. It also got $35 million in short-term financing from Axonic Capital, a New York hedge fund that specializes in commercial real estate transactions. The loan from Axonic was used to complete the purchase while Nelson Partners was raising money from investors.

Nelson Partners was to pay Axonic back the bridge loan, plus interest, using money raised from investors like Ms. Martinez. But Mr. Nelson’s firm did not pay back the loan, according to court filings. In February 2020, Axonic put Nelson Partners on notice, and it notified him last May that it was declaring Nelson Partners in default and taking control of the building.

Mr. Nelson opposed Axonic’s move but did not inform investors about his dealings with the hedge fund, according to the lawsuits. Instead, in April 2020, Nelson Partners stopped paying monthly cash dividends to the investors, telling them that it needed to conserve cash during the pandemic in the event students and their parents stopped paying rent. Mr. Nelson’s firm also received a loan of just over $1.2 million from the Small Business Administration’s Paycheck Protection Program.

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