Hillary Clinton Interviewed at Code Conference

On Wednesday, Hillary Clinton was interviewed at the Code Conference in Ranchos Palos Verdes, California. Clinton was interviewed at the annual event by veteran tech journalists, and Recode co-founders, Walt Mossberg and Kara Swisher. During their conversation, Clinton discussed losing the 2016 election, which she took the blame for. She did also place part of the blame on a number of other factors including the alleged hacking of the DNC and John Podesta by Russia, the letter sent to Congress by FBI Director James Comey, and incorrect data provided by the DNC. Clinton was also critical of the Democratic Party’s digital strategy saying that the party needed to get better at outreach. When asked whether she would remain active in politics, Clinton said, “I’m not going anywhere. I have a big stake in what happened in this country. I am very unbowed and unbroken about what happened because I don’t want it to happen to anybody else.” The full video of Clinton’s interview is below.

For all the latest, follow our Scheduled Events page and follow the Clintons on Twitter @HillaryClinton, @billclinton, and @ChelseaClinton. You can also follow Hillary on Facebook and Instagram.

News Source: Recode, Politico, Fortune, CNBC

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John Podesta Interviewed by The Global Politico

WASHINGTON, DC — NOVEMBER 9: Former Clinton White House Chief of Staff, John Podesta, being interviewed for Discovery Channel’s, “The President’s Gatekeepers,” November 9, 2012, in Washington, D.C. (Photo by David Hume Kennerly/Getty Images)

Former Hillary for America campaign chairman John Podesta was interviewed on the latest episode of The Global Politico podcast. While there are a few comments in the interview about the 2016 election, the majority of the interview is about President Donald Trump, his firing of FBI Director James Comey, and whether Republicans can impeach Trump without damaging the party. Podesta is critical of Trump’s presidency and still blames Comey for Clinton’s loss last November. He said, “I still think what Jim Comey did last fall was wrong, but he shouldn’t have been fired, given the circumstances that he was leading this investigation.” Read a transcript of the interview HERE, or you can listen to the interview below.

For all the latest, follow our Scheduled Events page and follow the Clintons on Twitter @HillaryClinton, @billclinton, and @ChelseaClinton. You can also follow Hillary on Facebook and Instagram.

News Source: Politico, Politico

Clinton Discusses Election at Women for Women Luncheon

On Tuesday afternoon, Hillary Clinton was a guest of the Women for Women International Luncheon in New York City. During the event, Clinton had a conversation with Christiane Amanpour. The two discussed a number of issues including the Donald Trump administration, a potential conflict with North Korea, and the 2016 presidential election. While Clinton accepted the blame for her loss, she said that there were a number of other factors including the letter from FBI Director James Comey and Russian hacking of the emails of the Democratic National Committee and Hillary for America Campaign Director John Podesta.

Clinton said she would have won the election if it had not been for the Comey letter and Wikileaks in late October adding, “If the election had been held on October 27, I’d be your president, and it wasn’t. It was on October 28.” Clinton did not deflect all of the blame saying that her campaign made mistakes. “I was the candidate, I was the person who was on the ballot and I am very aware of the challenges, the problems, the shortfalls that we had,” she admitted. Clinton vowed to remain active in politics as a citizen and urged everyone to do the same. Watch a video from the event below.

For all the latest, follow our Scheduled Events page and follow the Clintons on Twitter @HillaryClinton, @billclinton, and @ChelseaClinton. You can also follow Hillary on Facebook and Instagram.

News Source: CBS News, The Washington Post, Time, CNN, Politico

Judge Unseals Hillary Clinton FBI Search Warrant

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On Tuesday, a federal judge ordered that the search warrant that many have faulted for Hillary Clinton’s loss be unsealed. The warrant called for the investigation of emails between Clinton and aide Huma Abedin that were found on a laptop belonging to Abedin’s ex-husband, former Congressman Anthony Weiner. The document does not provide in detail what the FBI hoped to find, and the investigation ultimately turned up nothing. The warrant was approved by U.S. Magistrate Judge Kevin Nathaniel Fox.

Many people have criticized the timing of the investigation by the FBI and the manner in which FBI director James Comey handled the investigation. He sent a letter to Congress two weeks before the election saying that the email investigation had been reopened. A few days later they concluded that no new evidence was found, but the damage to Clinton had been done. Despite winning the popular vote, Clinton lost the electoral college and the presidency. Clinton and her former campaign staffers blame Comey and the Russian hacking of the Democratic National Committee and Hillary for America chair John Podesta for their loss.

Read a copy of the warrant below or download a PDF copy HERE.

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News Source: The Washington Post, USA Today, Fortune, ABC News, Newsweek

Podesta Pens Op-Ed about the FBI

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The chairman of Hillary Clinton’s presidential campaign, John Podesta, published an op-ed in The Washington Post criticizing the FBI for its handling of Clinton’s email investigation and the hacking of his emails as well as the emails of the Democratic National Committee. Read Podesta’s full op-ed below:

Something is deeply broken at the FBI
By: John Podesta
December 15, 2016

The more we learn about the Russian plot to sabotage Hillary Clinton’s campaign and elect Donald Trump, and the failure of the FBI to adequately respond, the more shocking it gets. The former acting director of the CIA has called the Russian cyberattack “the political equivalent of 9/11.” Just as after the real 9/11, we need a robust, independent investigation into what went wrong inside the government and how to better protect our country in the future.

As the former chair of the Clinton campaign and a direct target of Russian hacking, I understand just how serious this is. So I was surprised to read in the New York Times that when the FBI discovered the Russian attack in September 2015, it failed to send even a single agent to warn senior Democratic National Committee officials. Instead, messages were left with the DNC IT “help desk.” As a former head of the FBI cyber division told the Times, this is a baffling decision: “We are not talking about an office that is in the middle of the woods of Montana.”

What takes this from baffling to downright infuriating is that at nearly the exact same time that no one at the FBI could be bothered to drive 10 minutes to raise the alarm at DNC headquarters, two agents accompanied by attorneys from the Justice Department were in Denver visiting a tech firm that had helped maintain Clinton’s email server.

This trip was part of what FBI Director James B. Comey described as a “painstaking” investigation of Clinton’s emails, “requiring thousands of hours of effort” from dozens of agents who conducted at least 80 interviews and reviewed thousands of pages of documents. Of course, as Comey himself concluded, in the end, there was no case; it was not even a close call.

Comparing the FBI’s massive response to the overblown email scandal with the seemingly lackadaisical response to the very real Russian plot to subvert a national election shows that something is deeply broken at the FBI.

Comey justified his handling of the email case by citing “intense public interest.” He felt so strongly that he broke long-established precedent and disregarded strong guidance from the Justice Department with his infamous letter just 11 days before the election. Yet he refused to join the rest of the intelligence community in a statement about the Russian cyberattack because he reportedly didn’t want to appear “political.” And both before and after the election, the FBI has refused to say whether it is investigating Trump’s ties to Russia.

There are now reports that Vladimir Putin personally directed the covert campaign to elect Trump. So are teams of FBI agents busy looking into the reported meeting in Moscow this summer between Carter Page, a Trump foreign policy adviser, and the Putin aide in charge of Russian intelligence on the U.S. election? What about evidence that Roger Stone was in contact with WikiLeaks and knew in advance that my hacked emails were about to be leaked? Are thousands of FBI person-hours being devoted to uncovering Trump’s tangled web of debts and business deals with foreign entities in Russia and elsewhere?

Meanwhile, House Republicans who had an insatiable appetite for investigating Clinton have been resistant to probing deeply into Russia’s efforts to swing the election to Trump. The media, by gleefully publishing the gossipy fruits of Russian hacks, became what the Times itself calls “a de facto instrument of Russian intelligence.”

But the FBI’s role is particularly troubling because of its power and responsibility — and because this is part of a trend. The Justice Department’s Inspector General issued a damning report this summer about the FBI’s failure to prioritize cyberthreats more broadly.

The election is over and the damage is done, but the threat from Russia and other potential aggressors remains urgent and demands a serious and sustained response.

First, the Obama administration should quickly declassify as much as possible concerning what is known about the Russian hack, as requested by seven Democratic members of the Senate Intelligence Committee.

Second, the administration should brief members of the electoral college on the extent and manner of Russia’s interference in our election before they vote on Dec. 19, as requested by a bipartisan group of electors.

Third, Congress should authorize a far-reaching, bipartisan independent investigation modeled on the 9/11 Commission. The public deserves to know exactly what happened, why and what can be done to prevent future attacks. Reps. Eric Swalwell (D-Calif.) and Elijah E. Cummings (D-Md.) have introduced legislation to authorize such an investigation.

Finally, Congress should more vigorously exercise its oversight to determine why the FBI responded overzealously in the Clinton case and insufficiently in the Russian case. The FBI should also clarify whether there is an ongoing investigation into Trump, his associates and their ties to Russia. If ever there were a case of “intense public interest,” this is it. What’s broken in the FBI must be fixed and quickly.

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News Source: The Washington Post

Electors Ask for Intelligence Briefing Before Vote

A bipartisan group of electors from the Electoral College have asked for an intelligence briefing following revelations from the CIA that Russia may have influenced the election. In a letter to James Clapper, the Director of National Intelligence, the electors expressed their concern and asked that all of the electors be briefed by the intelligence community before they cast their ballots later this month. The chairman of Hillary Clinton’s campaign, John Podesta, said that he and the campaign supports the electors being briefed. In a statement, he said, “The bipartisan electors’ letter raises very grave issues involving our national security. Electors have a solemn responsibility under the Constitution and we support their efforts to have their questions addressed. Each day that month, our campaign decried the interference of Russia in our campaign and its evident goal of hurting our campaign to aid Donald Trump. Despite our protestations, this matter did not receive the attention it deserved by the media in the campaign. We now know that the CIA has determined Russia’s interference in our elections was for the purpose of electing Donald Trump. This should distress every American.”

This post will be updated as we learn more.

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News Source: The Washington Post, Politico

With Her Podcast: Episode 10: Jennifer Palmieri

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On the tenth episode of the With Her podcast, host Max Linsky sat down with Hillary Clinton’s communications director, Jennifer Palmieri. Linsky and Palmieri discuss the challenges of the campaign cycle. They also discuss Clinton’s career and how she has prepared for the office of president. You can listen to the episodes HERE or subscribe to the Podcast on iTunes or your favorite Podcast app.

For all the latest, follow our Scheduled Events page and follow Clinton on Twitter, Facebook, YouTube, and Instagram. Also, be sure to subscribe to the campaign’s official Podcast, With Her.

News Source: Hillary for America

FBI Director Comey Recommends No New Action Against Clinton

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FBI Director James Comey sent a letter to ranking members of Congress on Sunday with the bureau’s conclusions following an investigation into emails found on a computer owned by former Congressman Anthony Weiner. The emails were related to Hillary Clinton’s tenure as Secretary of State. In his letter, Comey says that the FBI stands by its decision to not bring a case against Clinton and that the new emails yielded no new information. Comes said that “based on our review, we have not changed our conclusions that we expressed in July with respect to Secretary Clinton.” Since the FBI announced it was looking into the emails last week, the Clinton campaign has maintained that there was nothing new to be found. News sources indicate that the majority of the emails found on the computer were duplicates of the emails already reviewed by the bureau. Read the full letter from the FBI director below or download a PDF HERE.

For all the latest, follow our Scheduled Events page and follow Clinton on TwitterFacebookYouTube, and Instagram. Also, be sure to subscribe to the campaign’s official Podcast, With Her.

News Source: The New York Times, The Washington Post, Politico

Statement on Trump’s Foreign Business Entanglements

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In response to new reporting from the Wall Street Journal on Donald Trump’s dangerous and unprecedented foreign business entanglements, Hillary for America deputy communications director Christina Reynolds issued the following statement:

“Donald Trump has business all around the world, and while he has failed to disclose full details of his business record, what we know is truly disturbing. The idea of a President Trump trying to negotiate with foreign leaders while having his business at stake is simply unacceptable and raises real questions about how he would handle matters of national security. This is just one more reason why he cannot be president.”

IN CASE YOU MISSED IT

KEY POINT: “Those whom Ivanka Trump, Donald Trump Jr. and Eric Trump have worked with abroad include: the family of a developer in India who is a ruling-party politician, an Azerbaijani government minister’s son and a media company that became the Turkish president’s outlet of choice during the July 15 coup attempt.

No recent president has had a portfolio of international business interests as extensive as Mr. Trump’s—or as great a level of business engagement on his behalf by offspring, who have also played a role in his campaign.”

For all the latest, follow our Scheduled Events page and follow Clinton on TwitterFacebookYouTube, and Instagram. Also, be sure to subscribe to the campaign’s official Podcast, With Her.

News Source: The Wall Street Journal

Statement on Trump’s “Legally Dubious” Tax Avoidance Scheme

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Calls on Trump to Release at Least 2015 Tax Returns, Which Are Not Under Audit

Yesterday, the New York Times published new documents that showed Trump engaged in “legally dubious” schemes to avoid paying millions in federal income taxes, even as his own lawyers made clear they likely would not hold up to IRS scrutiny. Trump’s campaign claims the reporting is not true, yet they refuse to produce the only evidence that could prove the Times wrong: Trump’s tax returns.

In response to the new report, Hillary for America deputy communications director Christina Reynolds issued the following statement:

“In the wake of a blockbuster report showing that even Trump’s own lawyers thought the IRS would likely find the “legally dubious” scheme he used to avoid taxes was against the law, the Trump campaign still refuses to release his tax returns. While breaking a precedent running for 40 years, Trump has clung to the excuse that he is under audit, despite no proof that he is and no prohibition for releasing returns under audit. Given that Trump was required to file his 2015 taxes recently, he has no reason to withhold it since it is too soon for him to possibly be under audit for those year. There’s no excuse left for Trump—if he’s not still using these “dubious” schemes to avoid paying taxes, he needs to prove it with his most recent tax returns.”

Trump and his campaign continue to dodge disclosure of these critical documents that could shed light on important issues including his wealth, his questionable charitable giving, his foreign and domestic business entanglements, his personal tax rate and more. The Times’ reporting raising important new questions that underscore the urgency in releasing the tax returns before Election Day.

Key Point: “As he scrambled to stave off financial ruin, Mr. Trump avoided reporting hundreds of millions of dollars in taxable income by using a tax avoidance maneuver so legally dubious his own lawyers advised him that the Internal Revenue Service would likely declare it improper if he were audited.”

  • “Tax experts who reviewed the newly obtained documents for The New York Times said Mr. Trump’s tax avoidance maneuver, conjured from ambiguous provisions of highly technical tax court rulings, clearly pushed the edge of the envelope of what tax laws permitted at the time. ‘Whatever loophole existed was not ‘exploited’ here, but stretched beyond any recognition,’ said Steven M. Rosenthal, a senior fellow at the nonpartisan Tax Policy Center who helped draft tax legislation in the early 1990s.”
  • “One letter, 25 pages long, analyzed seven distinct components of Mr. Trump’s proposed tax maneuver. It found only “substantial authority” for six of the components. In the stilted language of tax opinion letters, the phrase “substantial authority” is a red flag that the lawyers believe the I.R.S. can be expected to rule against the taxpayer roughly two-thirds of the time. In other words, Mr. Trump’s tax lawyers were telling him there were at least six different reasons the I.R.S. would likely cry foul if he were audited.”
  • “Regardless of whether the I.R.S. objected, Trump’s tax avoidance in this case violated a central principle of American tax law, said Mr. Buckley, the former chief of staff for Congress’s Joint Committee on Taxation, who later served as chief tax counsel for Democrats on the House Ways and Means Committee. ‘He deducted somebody else’s losses,’ Mr. Buckley said.”

IN CASE YOU MISSED IT

Donald Trump Used Legally Dubious Method to Avoid Paying Taxes

New York Times

By: David Barstow, Mike McIntire, Patricia Cohen, Susanne Craig, and Russ Buettner

October 31, 2016

Donald J. Trump proudly acknowledges he did not pay a dime in federal income taxes for years on end. He insists he merely exploited tax loopholes legally available to any billionaire — loopholes he says Hillary Clinton failed to close during her years in the United States Senate. “Why didn’t she ever try to change those laws so I couldn’t use them?” Mr. Trump asked during a campaign rally last month.

But newly obtained documents show that in the early 1990s, as he scrambled to stave off financial ruin, Mr. Trump avoided reporting hundreds of millions of dollars in taxable income by using a tax avoidance maneuver so legally dubious his own lawyers advised him that the Internal Revenue Service would likely declare it improper if he were audited.

Thanks to this one maneuver — which was later outlawed by Congress — Mr. Trump potentially escaped paying tens of millions of dollars in federal personal income taxes. It is impossible to know for sure because Mr. Trump has declined to release his tax returns, or even a summary of his returns, breaking a practice followed by every Republican and Democratic presidential candidate for more than four decades.

Tax experts who reviewed the newly obtained documents for The New York Times said Mr. Trump’s tax avoidance maneuver, conjured from ambiguous provisions of highly technical tax court rulings, clearly pushed the edge of the envelope of what tax laws permitted at the time. “Whatever loophole existed was not ‘exploited’ here, but stretched beyond any recognition,” said Steven M. Rosenthal, a senior fellow at the nonpartisan Tax Policy Center who helped draft tax legislation in the early 1990s.

Moreover, the tax experts said the maneuver trampled a core tenet of American tax policy by conferring enormous tax benefits to Mr. Trump for losing vast amounts of other people’s money — in this case, money investors and banks had entrusted to him to build a casino empire in Atlantic City.

As that empire floundered in the early 1990s, Mr. Trump pressured his financial backers to forgive hundreds of millions of dollars in debt he could not repay. While the cancellation of so much debt gave new life to Mr. Trump’s casinos, it created a potentially crippling problem with the Internal Revenue Service. In the eyes of the I.R.S., a dollar of canceled debt is the same as a dollar of taxable income. This meant Mr. Trump faced the painful prospect of having to report the hundreds of millions of dollars of canceled debt as if it were hundreds of millions of dollars of taxable income.

But Mr. Trump’s audacious tax-avoidance maneuver gave him a way to simply avoid reporting any of that canceled debt to the I.R.S. “He’s getting something for absolutely nothing,” John L. Buckley, who served as the chief of staff for Congress’s Joint Committee on Taxation in 1993 and 1994, said in an interview

The new documents, which include correspondence from Mr. Trump’s tax lawyers and bond offering disclosure statements, might also help explain how Mr. Trump reported a staggering loss of $916 million in his 1995 tax returns — portions of which were first published by The Times last month.

United States tax laws allowed Mr. Trump to use that $916 million loss to cancel out an equivalent amount of taxable income. But tax experts have been debating how Mr. Trump could have legally declared a deduction of that magnitude at all. Among other things, they have noted that Mr. Trump’s huge casino losses should have been offset by the hundreds of millions of dollars in taxable income he surely must have reported to the I.R.S. in the form of canceled casino debt.

By avoiding reporting his canceled casino debt in the first place, however, Mr. Trump’s $916 million deduction would not have been reduced by hundreds of millions of dollars. He could have preserved the deduction and used it instead to avoid paying income taxes he might otherwise have owed on books, TV shows or branding deals. Under the rules in effect in 1995, the $916 million loss could have been used to wipe out more than $50 million a year in taxable income for 18 years.

Mr. Trump declined to comment for this article.

“Your e-mail suggests either a fundamental misunderstanding or an intentional misreading of the law,” Hope Hicks, Mr. Trump’s spokeswoman, said in a statement. “Your thesis is a criticism, not just of Mr. Trump, but of all taxpayers who take the time and spend the money to try to comply with the dizzyingly complex and ambiguous tax laws without paying more tax than they owe. Mr. Trump does not think that taxpayers should file returns that resolve all doubt in favor of the I.R.S. And any tax experts that you have consulted are engaged in pure speculation. There is no news here.”

Mr. Trump financed his three Atlantic City gambling resorts with $1.3 billion in debt, most of it in the form of high interest junk bonds. By late 1990, after months of escalating operating losses, New Jersey casino regulators were warning that “a complete financial collapse of the Trump Organization was not out of the question.” By 1992, all three casinos had filed for bankruptcy and bondholders were ultimately forced to forgive hundreds of millions of dollars in debt to salvage at least part of their investment.

The story of how Mr. Trump sidestepped a potentially ruinous tax bill from that forgiven debt emerged from documents recently discovered by The Times during a search of the casino bankruptcy filings. The documents offer only a partial description of events, and none of Mr. Trump’s tax lawyers agreed to be interviewed for this article.

At the time, Mr. Trump would have been hard-pressed to pay tens of millions of dollars in taxes. According to assessments of his financial stability by New Jersey casino regulators, there were times in the early 1990s when Mr. Trump had no more than a few million dollars in his various bank accounts. He was so strapped for cash that his creditors were apoplectic when they learned that Mr. Trump had bought Marla Maples an engagement ring estimated to be worth $250,000.

It is unclear who first glimpsed a way for Mr. Trump to dodge a huge tax bill. But the basic maneuver he used was essentially a new twist on a contentious strategy corporations had been using for years to avoid taxes created by canceled debt.

The strategy — known among tax practitioners as a “stock-for-debt swap” — relies on mathematical sleight of hand. Say a company can repay only $60 million of a $100 million bank loan. If the bank forgives the remaining $40 million, the company faces a large tax bill because it will have to report that canceled $40 million debt as taxable income.

Clever tax lawyers found a way around this inconvenience. The company would simply swap stock for the $40 million in debt it could not repay. This way, it would look as if the entire $100 million loan had been repaid, and presto: There would be no tax bill due for $40 million in canceled debt.

Best of all, it did not matter if the actual market value of the stock was considerably less than the $40 million in canceled debt. (Stock in an effectively insolvent company could easily be next to worthless.) Even in the opaque, rarefied world of gaming impenetrable tax regulations, this particular maneuver was about as close as a company could get to waving a magic wand and making taxes disappear.

Alarmed by the obvious potential for abuse, Congress and the I.R.S. made repeated efforts during the 1980s to curb this brand of tax wizardry before banning its use by corporations altogether in 1993. But while policy makers were busy trying to stop corporations from using this particular ploy, the endlessly creative club of elite tax advisers was inventing a new way to circumvent the ban, this time through the use of partnerships.

This was the twist that was especially beneficial to Mr. Trump. Wealthy families like the Trumps often own real estate and other assets through partnerships rather than corporations. Mr. Trump, for example, owned all three of his Atlantic City casinos through partnerships, an arrangement that allowed casino profits to flow directly to his personal tax returns when times were good.

But what if times were bad? What if Mr. Trump’s casino partnerships could not repay hundreds of millions of dollars they owed to bondholders? And what if the bondholders were persuaded to forgive this debt? Wouldn’t that force the partnerships — i.e., Mr. Trump — to report hundreds of millions of dollars of taxable income in the form of canceled debt?

Enter the tax advisers with their audacious plan: Why not eliminate all that taxable income from canceled debt by swapping “partnership equity” for debt in exactly the same way corporations had been swapping company stock for debt.

True enough, the I.R.S. and Congress had clearly signaled their disapproval of the basic concept. Fred T. Goldberg, who was the I.R.S. commissioner under George Bush, recalled in an interview that the I.R.S. frowned on partnership equity-for-debt swaps for the same reason it objected to corporate stock-for-debt swaps. “The fiction is that the partnership interest has the same value as the debt,” he said. Lee A. Sheppard, a contributing editor to Tax Notes, wrote in 1991 that trying to find a legal justification for this tactic was akin to proving “the existence of the Loch Ness monster.”

On the campaign trail, Mr. Trump boasts of his mastery of tax loopholes and claims no other candidate for the White House has ever known more about the tax code. This background, he argues with evident disgust, gives him special insight into the way wealthy elites buy off politicians and hire high-priced lawyers and accountants to rig the tax system — just as, he claims, they rig elections.

That insight was on display in 1991 and 1992 when he was laying the groundwork to make a multimillion-dollar tax bill disappear.

Before proceeding with his plan, Mr. Trump did what most prudent taxpayers do — he sought a formal tax opinion letter. Such letters, typically written by highly-paid lawyers who spend entire careers mastering the roughly 10,000 pages of ever-changing statutes that make up the United States tax code, can provide important protection to taxpayers. As long as a tax adviser blesses a particular tax strategy in a formal opinion letter, the taxpayer most likely will not face penalties even if the I.R.S. ultimately rules the strategy was improper.

The language used in tax opinion letters has a specialized meaning understood by all tax professionals. So, for example, when a tax lawyer writes that a shelter is “more likely than not” going to be approved by the I.R.S., this means there is at least a 51 percent chance the shelter will withstand scrutiny. (This is known as an “M.L.T.N.” letter in the vernacular of tax lawyers.) A “should” letter means there is about a 75 percent chance the I.R.S. will not object. The gold standard, a “will” letter, means the I.R.S. is all but certain to bless the tax avoidance strategy.

But the opinion letters Mr. Trump received from his tax lawyers at Willkie Farr & Gallagher were far from the gold standard. The letters bluntly warned that there was no statute, regulation or judicial opinion that explicitly permitted Mr. Trump’s tax gambit. “Due to the lack of definitive judicial or administrative authority,” his lawyers wrote, “substantial uncertainties exist with respect to many of the tax consequences of the plan.”

One letter, 25 pages long, analyzed seven distinct components of Mr. Trump’s proposed tax maneuver. It found only “substantial authority” for six of the components. In the stilted language of tax opinion letters, the phrase “substantial authority” is a red flag that the lawyers believe the I.R.S. can be expected to rule against the taxpayer roughly two-thirds of the time. In other words, Mr. Trump’s tax lawyers were telling him there were at least six different reasons the I.R.S. would likely cry foul if he were audited. In anticipation of that possibility, the lawyers even laid out a fallback plan that would have allowed Mr. Trump to spread the pain of a large tax hit over many years if the I.R.S. ultimately balked.

It is unclear whether the I.R.S. ever challenged Mr. Trump’s use of this specific tax maneuver. According to a financial disclosure statement prepared by Mr. Trump’s accountants, he was under audit by tax authorities as of 1993, only a year after he avoided reporting hundreds of millions of dollars in taxable income because of this legally suspect tactic. But the results of that audit are unknown and the agency declined to comment on Monday.

Regardless of whether the I.R.S. objected, Mr. Trump’s tax avoidance in this case violated a central principle of American tax law, said Mr. Buckley, the former chief of staff for Congress’s Joint Committee on Taxation who later served as chief tax counsel for Democrats on the House Ways and Means Committee.

“He deducted somebody else’s losses,” Mr. Buckley said. By that Mr. Buckley means that only the bondholders who forgave Mr. Trump’s unpaid casino debts should have been allowed to use those losses to offset future income and reduce their taxes. That Mr. Trump used the same losses to reduce his taxes ultimately increases the tax burden on everyone else, Mr. Buckley explained. “He is double dipping big time.”

In any event, Mr. Trump can no longer benefit from the same maneuver. Just as Congress acted in 1993 to ban stock-for-debt swaps by corporations, it acted in 2004 to ban equity-for-debt swaps by partnerships.

Among the members of Congress who voted to finally close the loophole: Senator Hillary Clinton of New York.

For all the latest, follow our Scheduled Events page and follow Clinton on TwitterFacebookYouTube, and Instagram. Also, be sure to subscribe to the campaign’s official Podcast, With Her.