Analysis: Weisselberg indictment echoes Fred Trump's tactics on taxes

Long before Donald Trump's firm was accused of plotting detours around the tax code to compensate its chief financial officer with carpeting, televisions and car leases, there were the $16,135 boilers.

The boilers were bought for that amount by Trump's father, Fred, in the 1990s for his apartment buildings. But in a bit of financial alchemy that embodied the family ethos of paying as little tax as possible, the elder Trump used inflated invoices to pay the bill, and the extra money was skimmed off for his children — all to avoid gift and inheritance taxes.

Echoes of the earlier scheme could be found in the indictment Thursday of the Trump Organization and CFO Allen Weisselberg, who first went to work for Fred Trump in the 1970s. While the amount of tax-free benefits that Weisselberg reportedly received is significant — $1.76 million over 15 years — the way the company went about doling them out is strikingly small-bore and incremental.

In fact, the first criminal case against the former president's company features no grand schemes to launder money through Russia, hide millions offshore or commit other offenses commensurate with a self-described global business empire headquartered on Fifth Avenue. Rather, details of the charges brought by a Manhattan grand jury have a rather low-rent feel that one might associate with a scrappy real estate operation born in Brooklyn and Queens.

Which, of course, it is.

The Trump Organization has always been a family business, tightly controlled by Trump and a small number of relatives and trusted associates, including Weisselberg. Although the company has about 3,500 employees worldwide, most are lower-tier workers at golf resorts and hotels, and only 122 made $100,000 or more in 2018, according to tax records for Trump and his businesses obtained by the New York Times.

The tax records, which the Times reported on last year, also reveal a deep commitment to maneuvering to winnow taxes to a minimum. Hundreds of millions of dollars in deductions for business expenses ran the gamut, from $6 for food in Uruguay and $10 for using a telephone in Panama to $13.7 million for "sales and marketing" in Las Vegas.

The Manhattan District Attorney's Office and New York state's attorney general are also investigating whether the company intentionally overvalued a 50,000-square-foot mansion in Westchester County to claim a $21 million tax write-off for a conservation easement. Both agencies are also examining the Trump Organization's practice of deducting millions of dollars in consulting fees, some of which appear to have been paid to at least one of Trump's children who was a full-time company employee at the time she received them.

No charges have been filed related to those inquiries, and Trump himself has not been charged. Both Weisselberg and the Trump Organization denied the charges, and Trump has called the investigations, which were initiated by elected Democrats, a politically motivated "witch hunt."

The Trump Organization's relentless quest for tax avoidance has its roots in Fred Trump's determination to fend off the taxman at every possible turn. A self-made workaholic, the elder Trump eventually passed more than $1 billion to his children while employing legally dubious strategies to avoid nearly $500 million in taxes on the transfers, a 2018 investigation by the Times found.

Among the Trump family's machinations was the creation in 1992 of All County Building Supply & Maintenance, a company that existed mainly on paper. It was co-owned by Donald Trump, his three siblings and a cousin, John Walter.

Vendors who sold goods and services to Trump properties were asked to send invoices to All County, which would pad the actual cost by an additional 20% or more and bill Fred Trump, who paid the inflated amount. The extra money was then split among the former president, his siblings and cousin.

"He loved to save taxes," Walter said.

It is a lesson fully absorbed by his eager-to-please son Donald Trump, who has bragged about avoiding taxes. When his 2016 Democratic opponent, Hillary Clinton, accused him during a debate of not paying federal income taxes, Trump replied, "That makes me smart."

The Times' 2020 investigation of Trump's tax records found that by using hundreds of millions in losses from his businesses as well as by deducting expenses and taking advantage of tax credits, he was able to pay only $750 in U.S. income taxes in both 2016 and 2017 and none at all in 10 of the previous 15 years. His aggressive strategies led to an IRS audit of the legitimacy of a $72.9 million refund he claimed.

The indictment announced Thursday accuses the Trump Organization of a new series of off-the-books maneuvers that in some respects resemble an updated version of Fred Trump's model. In Weisselberg's case, rather than simply receiving a higher salary, his base pay was set at $540,000 and then augmented with a series of benefits designed to avoid income and payroll taxes, the indictment alleges.

Some of the extra benefits to Weisselberg and other Trump Organization employees came from annual bonuses drawn from various corporate entities controlled by the company and classified as "non-employee" pay, which allowed Weisselberg to reduce his income taxes by putting the money into a type of retirement account intended for people who are self-employed. The Trump Organization also paid the rent for his apartment, Mercedes-Benz leases and private school tuition, none of which was reported as taxable income.