O'Rourke says he has donated much more to charity than reflected in tax returns
Legal obstacles to pursuing tax charges against Trump family
New York officials are looking for ways to go after President Trump following a blockbuster story detailing his family's tax practices. But experts say any efforts by federal and state authorities to impose penalties on the president would face serious legal and practical obstacles.
The New York Times on Tuesday published an investigative report, based on a review of more than 100,000 pages of documents, describing "dubious" tax schemes that the president and his family engaged in during the 1990s so that his parents could avoid gift and estate taxes. The article prompted calls for government probes.
A spokesman for the New York State tax and finance department said the agency is "vigorously pursuing all appropriate avenues of investigation."
New York City Mayor Bill de Blasio (D) said the city would seek to recover any money owed by the president and the city's deputy mayor told the Times on Thursday that it would look into whether there were underpaid real estate transfer taxes and property taxes.
And congressional Democrats are calling for investigations, as well as the release of the president's tax returns.
"There is a reason why the president has refused to release his tax returns and we are starting to see why," Sen. Kirsten Gillibrand (D-N.Y.) said in a statement to The Hill. "Nobody should be above the law, there should be an investigation, and if he committed fraud, he should face the same consequences as anyone else and every penny should be paid back."
Tax lawyers, however, say an investigation would be challenging, particularly because the practices cited in the Times article occurred years, even decades ago.
"I think this is probably a frustrating situation for the tax authorities," said Danshera Cords, a professor at Albany Law School who specializes in corporate and individual taxes.
The Times article detailed several ways the Trump family minimized the estate-tax bill of the president's parents, such as undervaluing properties and establishing a "sham" company used to hide gifts.
The president called the article a "hit piece."
Lee-Ford Tritt, a University of Florida law professor who reviewed some of the documents cited by the Times during the reporting process, told The Hill that the newspaper's research was "amazingly thorough."
Tritt said while he can't say with certainty that the Trump family committed tax fraud, he would characterize various actions as "highly suspicious."
"There is substantial circumstantial evidence that shows that valuations may have been exaggerated," he said.
Under federal and state laws, the statute of limitations most likely has run out on criminal tax charges. However, there is no statute of limitations for civil tax fraud, meaning New York state and the IRS could seek back taxes and financial penalties.
Tax experts also said authorities will be able to look at the years when Trump's father didn't file a gift tax return. The IRS sought back taxes several years ago from media magnate Sumner Redstone for a gift he made in 1972 for which he did not file a return.
But lawyers and accountants said tax fraud is difficult to prove, and they noted that key players - the president's parents - are dead. They said there also are non-tax allegations of wrongdoing in the Times story that authorities could investigate, but that punitive measures may be tough to impose because of how many years have passed.
Experts said an added challenge for a possible IRS investigation is that the agency has already audited the estates of Trump's parents and presumably issued a closing agreement. The Times reported that the IRS concluded the estates had a value of $51.8 million, more than the president and his siblings had said it was worth.
"For the estate itself, it is probably not likely that the IRS would go back and review the gifts from the father or the valuation of the discounts," said Hal Terr, a certified public accountant and partner at Withum in Princeton, N.J.
"On the federal level, I would not really expect much to come out of this," said Beth Shapiro Kaufman, tax and estate-planning lawyer at Caplin & Drysdale in Washington.
An IRS spokesperson declined to comment on the Times story and whether the agency would take any action as a result of the article.
Investigating years-old events is difficult at the state level as well. But New York politicians have demonstrated an interest in going after Trump, who is unpopular in the heavily Democratic state.
In June, the New York attorney general filed a lawsuit against the Donald J. Trump Foundation, alleging that it engaged in improper political activity.
Cords said the state will at a minimum conduct an investigation into elements of the New York Times story.
"I know it's not an easy case to make, but they tend to aggressively pursue tax crimes," she said, noting that the state has been aggressive in investigating Trump.
Cords added that even if the state can't prove fraud based on the information in the Times story, it may be able to use the article as a starting point to seek out more-recent wrongdoing.
Jennifer Boll - a lawyer at Bond, Schoeneck and King PLLC in Albany - said New York often vigorously pursues estate-tax audits, particularly when taxpayers say they don't have to file estate-tax returns because they're not state residents.
"I would think they would be pretty vigilant," she said.