New York prosecutors are investigating whether the Trump Organization broke the law by offering dramatically different valuations of the same properties

• New York prosecutors are investigating the Trump Organization's history of claiming dramatically different valuations of its properties.
• The company valued several properties up to 30 times more for potential lenders than for tax officials, The Washington Post reported.

The Manhattan district attorney and New York attorney general are investigating several instances in which the Trump Organization provided government officials and potential lenders vastly different valuations of its properties.

The prosecutors are said to be presenting the evidence at a second special grand jury they empaneled in Manhattan for their long-running investigation into the Trump Organization's finances. Investigations appear to be focusing their efforts on at least four of former President Donald Trump's properties: an office building at 40 Wall Street in Manhattan; a golf club in Rancho Palos Verdes, California; an estate called Seven Springs in Westchester County, New York; and a golf club in Briarcliff Manor, New York.

Trump's company valued these properties up to 30 times more depending on who the numbers were provided to, according to documentation obtained by The Washington Post. In 2012, the Trump Organization told tax officials the Manhattan office building was worth just $16.7 million. But just a few months prior, the company had valued the same building at a staggering $527 million in a document provided to possible lenders, The Post reported.

In another instance in 2013, the Trump Organization told county tax officials that its California golf club was worth $900,000. But in 2014, as the company was seeking a massive tax deduction through a conservation easement, it said the same property was worth at least $25 million. It was in Trump's financial interest to inflate the value of the land when asking for an easement, which limits commercial use of the land, because it would amount to a larger tax break.

Prosecutors are investigating whether the different valuations amount to crimes

Manhattan District Attorney Cyrus Vance Jr. obtained reams of documentation from the Trump Organization from subpoenas in 2020. The documentation may include tax forms, as well as communications between company officials and third-party tax preparers that can shed light on how the company came to the different property evaluations.

Along with the office of New York Attorney General Letitia James — a Democrat who recently announced her bid for governor — Vance is said to be weighing whether the differences in property evaluation amounted to tax, bank, or insurance fraud. James is also running a concurrent civil investigation that may result in a lawsuit against the company.

Jeff Robbins, a former attorney for the US Senate Permanent Subcommittee on Investigations and federal prosecutor overseeing money-laundering probes, previously told Insider that keeping two sets of books could indicate the Trump Organization broke financial laws.

"Inconsistency is not a crime. The intent to defraud is a crime," Robbins told Insider. "What a prosecutor is going to be looking at is: Did Trump seek to defraud the government of the United States with respect to the valuation of assets and the paying of taxes? Was there an intent to defraud banks?"

Michael Cohen, Trump's longtime former "fixer" and attorney, told Congress in 2019 that Trump regularly inflated his wealth and the value of his assets to insurers and lenders and then turned around and undervalued his assets to pay less in taxes. Cohen was sentenced to three years in federal prison in 2018 for violating campaign finance laws to help Trump during the 2016 election, lying to Congress, and other financial crimes.

Prosecutors are also examining whether Trump Organization executives avoided paying taxes by illegally accepting tax-free perks like apartments and the use of company cars. In July, another grand jury empaneled by the Manhattan district attorney's and New York attorney general's offices indicted the Trump Organization on charges of criminal tax fraud, alleging it operated a 15-year scheme helping top executives evade income taxes. The grand jury also charged the Trump Organization's longtime Chief Financial Officer Allen Weisselberg, alleging he oversaw the scheme and personally evaded income taxes on about $1.7 million in perks he received from the company.

Trump has broadly dismissed the investigations and accused Democrats of digging around in search of crimes. Earlier this year, he called the New York inquiries "a continuation of the greatest political Witch Hunt in the history of the United States."