Trump Engaged in Suspect Tax Schemes as He Reaped Riches From His Father

The president has long sold himself as a self-made billionaire, but a Times investigation found that he received at least $413 million in today’s dollars from his father’s real estate empire, much of it through tax dodges in the 1990s.

By DAVID BARSTOW, SUSANNE CRAIG and RUSS BUETTNER

President Trump participated in dubious tax schemes during the 1990s, including instances of outright fraud, that greatly increased the fortune he received from his parents, an investigation by The New York Times has found.

Mr. Trump won the presidency proclaiming himself a self-made billionaire, and he has long insisted that his father, the legendary New York City builder Fred C. Trump, provided almost no financial help.

But The Times’s investigation, based on a vast trove of confidential tax returns and financial records, reveals that Mr. Trump received the equivalent today of at least $413 million from his father’s real estate empire, starting when he was a toddler and continuing to this day.

Much of this money came to Mr. Trump because he helped his parents dodge taxes. He and his siblings set up a sham corporation to disguise millions of dollars in gifts from their parents, records and interviews show. Records indicate that Mr. Trump helped his father take improper tax deductions worth millions more. He also helped formulate a strategy to undervalue his parents’ real estate holdings by hundreds of millions of dollars on tax returns, sharply reducing the tax bill when those properties were transferred to him and his siblings.

These maneuvers met with little resistance from the Internal Revenue Service, The Times found. The president’s parents, Fred and Mary Trump, transferred well over $1 billion in wealth to their children, which could have produced a tax bill of at least $550 million under the 55 percent tax rate then imposed on gifts and inheritances.

The Trumps paid a total of $52.2 million, or about 5 percent, tax records show.

The president declined repeated requests over several weeks to comment for this article. But a lawyer for Mr. Trump, Charles J. Harder, provided a written statement on Monday, one day after The Times sent a detailed description of its findings. “The New York Times’s allegations of fraud and tax evasion are 100 percent false, and highly defamatory,” Mr. Harder said. “There was no fraud or tax evasion by anyone. The facts upon which The Times bases its false allegations are extremely inaccurate.”

Mr. Harder sought to distance Mr. Trump from the tax strategies used by his family, saying the president had delegated those tasks to relatives and tax professionals. “President Trump had virtually no involvement whatsoever with these matters,” he said. “The affairs were handled by other Trump family members who were not experts themselves and therefore relied entirely upon the aforementioned licensed professionals to ensure full compliance with the law.”

[Read the full statement]

The president’s brother, Robert Trump, issued a statement on behalf of the Trump family:

“Our dear father, Fred C. Trump, passed away in June 1999. Our beloved mother, Mary Anne Trump, passed away in August 2000. All appropriate gift and estate tax returns were filed, and the required taxes were paid. Our father’s estate was closed in 2001 by both the Internal Revenue Service and the New York State tax authorities, and our mother’s estate was closed in 2004. Our family has no other comment on these matters that happened some 20 years ago, and would appreciate your respecting the privacy of our deceased parents, may God rest their souls.”

The Times’s findings raise new questions about Mr. Trump’s refusal to release his income tax returns, breaking with decades of practice by past presidents. According to tax experts, it is unlikely that Mr. Trump would be vulnerable to criminal prosecution for helping his parents evade taxes, because the acts happened too long ago and are past the statute of limitations. There is no time limit, however, on civil fines for tax fraud.

The findings are based on interviews with Fred Trump’s former employees and advisers and more than 100,000 pages of documents describing the inner workings and immense profitability of his empire. They include documents culled from public sources — mortgages and deeds, probate records, financial disclosure reports, regulatory records and civil court files.

The investigation also draws on tens of thousands of pages of confidential records — bank statements, financial audits, accounting ledgers, cash disbursement reports, invoices and canceled checks. Most notably, the documents include more than 200 tax returns from Fred Trump, his companies and various Trump partnerships and trusts. While the records do not include the president’s personal tax returns and reveal little about his recent business dealings at home and abroad, dozens of corporate, partnership and trust tax returns offer the first public accounting of the income he received for decades from various family enterprises.

[11 takeaways from The Times’s investigation]

What emerges from this body of evidence is a financial biography of the 45th president fundamentally at odds with the story Mr. Trump has sold in his books, his TV shows and his political life. In Mr. Trump’s version of how he got rich, he was the master dealmaker who broke free of his father’s “tiny” outer-borough operation and parlayed a single $1 million loan from his father (“I had to pay him back with interest!”) into a $10 billion empire that would slap the Trump name on hotels, high-rises, casinos, airlines and golf courses the world over. In Mr. Trump’s version, it was always his guts and gumption that overcame setbacks. Fred Trump was simply a cheerleader.

“I built what I built myself,” Mr. Trump has said, a narrative that was long amplified by often-credulous coverage from news organizations, including The Times.

Certainly a handful of journalists and biographers, notably Wayne Barrett, Gwenda Blair, David Cay Johnston and Timothy L. O’Brien, have challenged this story, especially the claim of being worth $10 billion. They described how Mr. Trump piggybacked off his father’s banking connections to gain a foothold in Manhattan real estate. They poked holes in his go-to talking point about the $1 million loan, citing evidence that he actually got $14 million. They told how Fred Trump once helped his son make a bond payment on an Atlantic City casino by buying $3.5 million in casino chips.

But The Times’s investigation of the Trump family’s finances is unprecedented in scope and precision, offering the first comprehensive look at the inherited fortune and tax dodges that guaranteed Donald J. Trump a gilded life. The reporting makes clear that in every era of Mr. Trump’s life, his finances were deeply intertwined with, and dependent on, his father’s wealth.

By age 3, Mr. Trump was earning $200,000 a year in today’s dollars from his father’s empire. He was a millionaire by age 8. By the time he was 17, his father had given him part ownership of a 52-unit apartment building. Soon after Mr. Trump graduated from college, he was receiving the equivalent of $1 million a year from his father. The money increased with the years, to more than $5 million annually in his 40s and 50s.

Fred Trump’s real estate empire was not just scores of apartment buildings. It was also a mountain of cash, tens of millions of dollars in profits building up inside his businesses, banking records show. In one six-year span, from 1988 through 1993, Fred Trump reported $109.7 million in total income, now equivalent to $210.7 million. It was not unusual for tens of millions in Treasury bills and certificates of deposit to flow through his personal bank accounts each month.

Fred Trump was relentless and creative in finding ways to channel this wealth to his children. He made Donald not just his salaried employee but also his property manager, landlord, banker and consultant. He gave him loan after loan, many never repaid. He provided money for his car, money for his employees, money to buy stocks, money for his first Manhattan offices and money to renovate those offices. He gave him three trust funds. He gave him shares in multiple partnerships. He gave him $10,000 Christmas checks. He gave him laundry revenue from his buildings.

Much of his giving was structured to sidestep gift and inheritance taxes using methods tax experts described to The Times as improper or possibly illegal. Although Fred Trump became wealthy with help from federal housing subsidies, he insisted that it was manifestly unfair for the government to tax his fortune as it passed to his children. When he was in his 80s and beginning to slide into dementia, evading gift and estate taxes became a family affair, with Donald Trump playing a crucial role, interviews and newly obtained documents show.

The line between legal tax avoidance and illegal tax evasion is often murky, and it is constantly being stretched by inventive tax lawyers. There is no shortage of clever tax avoidance tricks that have been blessed by either the courts or the I.R.S. itself. The richest Americans almost never pay anything close to full freight. But tax experts briefed on The Times’s findings said the Trumps appeared to have done more than exploit legal loopholes. They said the conduct described here represented a pattern of deception and obfuscation, particularly about the value of Fred Trump’s real estate, that repeatedly prevented the I.R.S. from taxing large transfers of wealth to his children.

“The theme I see here through all of this is valuations: They play around with valuations in extreme ways,” said Lee-Ford Tritt, a University of Florida law professor and a leading expert in gift and estate tax law. “There are dramatic fluctuations depending on their purpose.”

The manipulation of values to evade taxes was central to one of the most important financial events in Donald Trump’s life. In an episode never before revealed, Mr. Trump and his siblings gained ownership of most of their father’s empire on Nov. 22, 1997, a year and a half before Fred Trump’s death. Critical to the complex transaction was the value put on the real estate. The lower its value, the lower the gift taxes. The Trumps dodged hundreds of millions in gift taxes by submitting tax returns that grossly undervalued the properties, claiming they were worth just $41.4 million.

The same set of buildings would be sold off over the next decade for more than 16 times that amount.

The most overt fraud was All County Building Supply & Maintenance, a company formed by the Trump family in 1992. All County’s ostensible purpose was to be the purchasing agent for Fred Trump’s buildings, buying everything from boilers to cleaning supplies. It did no such thing, records and interviews show. Instead All County siphoned millions of dollars from Fred Trump’s empire by simply marking up purchases already made by his employees. Those millions, effectively untaxed gifts, then flowed to All County’s owners — Donald Trump, his siblings and a cousin. Fred Trump then used the padded All County receipts to justify bigger rent increases for thousands of tenants.

After this article was published on Tuesday, a spokesman for the New York State Department of Taxation and Finance said the agency was “reviewing the allegations” and “vigorously pursuing all appropriate areas of investigation.”

All told, The Times documented 295 streams of revenue that Fred Trump created over five decades to enrich his son. In most cases his four other children benefited equally. But over time, as Donald Trump careened from one financial disaster to the next, his father found ways to give him substantially more money, records show. Even so, in 1990, according to previously secret depositions, Mr. Trump tried to have his father’s will rewritten in a way that Fred Trump, alarmed and angered, feared could result in his empire’s being used to bail out his son’s failing businesses.

Of course, the story of how Donald Trump got rich cannot be reduced to handouts from his father. Before he became president, his singular achievement was building the brand of Donald J. Trump, Self-Made Billionaire, a brand so potent it generated hundreds of millions of dollars in revenue through TV shows, books and licensing deals.

Constructing that image required more than Fred Trump’s money. Just as important were his son’s preternatural marketing skills and always-be-closing competitive hustle. While Fred Trump helped finance the accouterments of wealth, Donald Trump, master self-promoter, spun them into a seductive narrative. Fred Trump’s money, for example, helped build Trump Tower, the talisman of privilege that established his son as a major player in New York. But Donald Trump recognized and exploited the iconic power of Trump Tower as a primary stage for both “The Apprentice” and his presidential campaign.

The biggest payday he ever got from his father came long after Fred Trump’s death. It happened quietly, without the usual Trumpian news conference, on May 4, 2004, when Mr. Trump and his siblings sold off the empire their father had spent 70 years assembling with the dream that it would never leave his family.

Donald Trump’s cut: $177.3 million, or $236.2 million in today’s dollars.

‘One-Man Building Show’

Early experience, cultivated connections and a wave of federal housing subsidies helped Fred Trump lay the foundation of his son’s wealth.

Before he turned 20, Fred Trump had already built and sold his first home. At age 35, he was building hundreds of houses a year in Brooklyn and Queens. By 45, he was building some of the biggest apartment complexes in the country.

Aside from an astonishing work ethic — “Sleeping is a waste of time,” he liked to say — the growth reflected his shrewd application of mass-production techniques. The Brooklyn Daily Eagle called him “the Henry Ford of the home-building industry.” He would erect scaffolding a city block long so his masons, sometimes working a second shift under floodlights, could throw up a dozen rowhouses in a week. They sold for about $115,000 in today’s dollars.

By 1940, American Builder magazine was taking notice, devoting a spread to Fred Trump under the headline “Biggest One-Man Building Show.” The article described a swaggering lone-wolf character who paid for everything — wages, supplies, land — from a thick wad of cash he carried at all times, and whose only help was a secretary answering the phone in an office barely bigger than a parking space. “He is his own purchasing agent, cashier, paymaster, building superintendent, construction engineer and sales director,” the article said.

It wasn’t that simple. Fred Trump had also spent years ingratiating himself with Brooklyn’s Democratic machine, giving money, doing favors and making the sort of friends (like Abraham D. Beame, a future mayor) who could make life easier for a developer. He had also assembled a phalanx of plugged-in real estate lawyers, property appraisers and tax accountants who protected his interests.

All these traits — deep experience, nimbleness, connections, a relentless focus on the efficient construction of homes for the middle class — positioned him perfectly to ride a growing wave of federal spending on housing. The wave took shape with the New Deal, grew during the World War II rush to build military housing and crested with the postwar imperative to provide homes for returning G.I.s. Fred Trump would become a millionaire many times over by making himself one of the nation’s largest recipients of cheap government-backed building loans, according to Gwenda Blair’s book “The Trumps: Three Generations of Builders and a President.”

Those same loans became the wellspring of Donald Trump’s wealth. In the late 1940s, Fred Trump obtained roughly $26 million in federal loans to build two of his largest developments, Beach Haven Apartments, near Coney Island, Brooklyn, and Shore Haven Apartments, a few miles away. Then he set about making his children his landlords.

As ground lease payments fattened his children’s trusts, Fred Trump embarked on a far bigger transfer of wealth. Records obtained by The Times reveal how he began to build or buy apartment buildings in Brooklyn and Queens and then gradually, without public trace, transfer ownership to his children through a web of partnerships and corporations. In all, Fred Trump put up nearly $13 million in cash and mortgage debt to create a mini-empire within his empire — eight buildings with 1,032 apartments — that he would transfer to his children.

The handover began just before Donald Trump’s 16th birthday. On June 1, 1962, Fred Trump transferred a plot of land in Queens to a newly created corporation. While he would be its president, his children would be its owners, records show. Then he constructed a 52-unit building called Clyde Hall.

It was easy money for the Trump children. Their father took care of everything. He bought the land, built the apartments and obtained the mortgages. His employees managed the building. The profits, meanwhile, went to his children. By the early 1970s, Fred Trump would execute similar transfers of the other seven buildings.

For Donald Trump, this meant a rapidly growing new source of income. When he was in high school, his cut of the profits was about $17,000 a year in today’s dollars. His share exceeded $300,000 a year soon after he graduated from college.

How Fred Trump transferred 1,032 apartments to his children without incurring hundreds of thousands of dollars in gift taxes is unclear. A review of property records for the eight buildings turned up no evidence that his children bought them outright. Financial records obtained by The Times reveal only that all of the shares in the partnerships and corporations set up to create the mini-empire shifted at some point from Fred Trump to his children. Yet his tax returns show he paid no gift taxes on seven of the buildings, and only a few thousand dollars on the eighth.

That building, Sunnyside Towers, a 158-unit property in Queens, illustrates Fred Trump’s catch-me-if-you-can approach with the I.R.S., which had repeatedly cited him for underpaying taxes in the 1950s and 1960s.

Sunnyside was bought for $2.5 million in 1968 by Midland Associates, a partnership Fred Trump formed with his children for the transaction. In his 1969 tax return, he reported giving each child 15 percent of Midland Associates. Based on the amount of cash put up to buy Sunnyside, the value of this gift should have been $93,750. Instead, he declared a gift of only $6,516.

Donald Trump went to work for his father after graduating from the University of Pennsylvania in 1968. His father made him vice president of dozens of companies. This was also the moment Fred Trump telegraphed what had become painfully obvious to his family and employees: He did not consider his eldest son, Fred Trump Jr., a viable heir apparent.

Fred Jr., seven and a half years older than Donald, had also worked for his father after college. It did not go well, relatives and former employees said in interviews. Fred Trump openly ridiculed him for being too nice, too soft, too lazy, too fond of drink. He frowned on his interests in flying and music, could not fathom why he cared so little for the family business. Donald, witness to his father’s deepening disappointment, fashioned himself Fred Jr.’s opposite — the brash tough guy with a killer instinct. His reward was to inherit his father’s dynastic dreams.

Fred Trump began taking steps that enriched Donald alone, introducing him to the charms of building with cheap government loans. In 1972, father and son formed a partnership to build a high-rise for the elderly in East Orange, N.J. Thanks to government subsidies, the partnership got a nearly interest-free $7.8 million loan that covered 90 percent of construction costs. Fred Trump paid the rest.

But his son received most of the financial benefits, records show. On top of profit distributions and consulting fees, Donald Trump was paid to manage the building, though Fred Trump’s employees handled day-to-day management. He also pocketed what tenants paid to rent air-conditioners. By 1975, Donald Trump’s take from the building was today’s equivalent of nearly $305,000 a year.

Fred Trump also gave his son an extra boost through his investment, in the early 1970s, in the sprawling Starrett City development in Brooklyn, the largest federally subsidized housing project in the nation. The investment, which promised to generate huge tax write-offs, was tailor-made for Fred Trump; he would use Starrett City’s losses to avoid taxes on profits from his empire.

Fred Trump invested $5 million. A separate partnership established for his children invested $1 million more, showering tax breaks on the Trump children for decades to come. They helped Donald Trump avoid paying any federal income taxes at all in 1978 and 1979. But Fred Trump also deputized him to sell a sliver of his Starrett City shares, a sweetheart deal that generated today’s equivalent of more than $1 million in “consulting fees.”

The money from consulting and management fees, ground leases, the mini-empire and his salary all combined to make Donald Trump indisputably wealthy years before he sold his first Manhattan apartment. By 1975, when he was 29, he had collected nearly $9 million in today’s dollars from his father, The Times found.

Wealthy, yes. But a far cry from the image father and son craved for Donald Trump.

The Silent Partner

Fred Trump would play a crucial role in building and carefully maintaining the myth of Donald J. Trump, Self-Made Billionaire.

“He is tall, lean and blond, with dazzling white teeth, and he looks ever so much like Robert Redford. He rides around town in a chauffeured silver Cadillac with his initials, DJT, on the plates. He dates slinky fashion models, belongs to the most elegant clubs and, at only 30 years of age, estimates that he is worth ‘more than $200 million.’”

So began a Nov. 1, 1976, article in The Times, one of the first major profiles of Donald Trump and a cornerstone of decades of mythmaking about his wealth. How could he claim to be worth more than $200 million when, as he divulged years later to casino regulators, his 1976 taxable income was $24,594? Donald Trump simply appropriated his father’s entire empire as his own.

In the chauffeured Cadillac, Donald Trump took The Times’s reporter on a tour of what he called his “jobs.” He told her about the Manhattan hotel he planned to convert into a Grand Hyatt (his father guaranteed the construction loan), and the Hudson River railroad yards he planned to develop (the rights were purchased by his father’s company). He showed her “our philanthropic endeavor,” the high-rise for the elderly in East Orange (bankrolled by his father), and an apartment complex on Staten Island (owned by his father), and their “flagship,” Trump Village, in Brooklyn (owned by his father), and finally Beach Haven Apartments (owned by his father). Even the Cadillac was leased by his father.

“So far,” he boasted, “I’ve never made a bad deal.”

It was a spectacular con, right down to the priceless moment when Mr. Trump confessed that he was “publicity shy.” By claiming his father’s wealth as his own, Donald Trump transformed his place in the world. A brash 30-year-old playboy worth more than $200 million proved irresistible to New York City’s bankers, politicians and journalists.

Yet for all the spin about cutting his own path in Manhattan, Donald Trump was increasingly dependent on his father. Weeks after The Times’s profile ran, Fred Trump set up still more trusts for his children, seeding each with today’s equivalent of $4.3 million. Even into the early 1980s, when he was already proclaiming himself one of America’s richest men, Donald Trump remained on his father’s payroll, drawing an annual salary of $260,000 in today’s dollars.

Meanwhile, Fred Trump and his companies also began extending large loans and lines of credit to Donald Trump. Those loans dwarfed what the other Trumps got, the flow so constant at times that it was as if Donald Trump had his own Money Store. Consider 1979, when he borrowed

1.5 million in January, $65,000 in February, $122,000 in March, $150,000 in April, $192,000 in May, $226,000 in June, $2.4 million in July and $40,000 in August, according to records filed with New Jersey casino regulators.

In theory, the money had to be repaid. In practice, records show, many of the loans were more like gifts. Some were interest-free and had no repayment schedule. Even when loans charged interest, Donald Trump frequently skipped payments.

This previously unreported flood of loans highlights a clear pattern to Fred Trump’s largess. When Donald Trump began expensive new projects, his father increased his help. In the late 1970s, when Donald Trump was converting the old Commodore Hotel into a Grand Hyatt, his father stepped up with a spigot of loans. Fred Trump did the same with Trump Tower in the early 1980s.

In the mid-1980s, as Donald Trump made his first forays into Atlantic City, Fred Trump devised a plan that sharply increased the flow of money to his son.

The plan involved the mini-empire — the eight buildings Fred Trump had transferred to his children. He converted seven of them into cooperatives, and helped his children convert the eighth. That meant inviting tenants to buy their apartments, generating a three-way windfall for Donald Trump and his siblings: from selling units, from renting unsold units and from collecting mortgage payments.

In 1982, Donald Trump made today’s equivalent of about $380,000 from the eight buildings. As the conversions continued and Fred Trump’s employees sold off more units, his son’s share of profits jumped, records show. By 1987, with the conversions completed, his son was making today’s equivalent of $4.5 million a year off the eight buildings.

Fred Trump made one other structural change to his empire that produced a big new source of revenue for Donald Trump and his siblings. He made them his bankers.

The Times could find no evidence that the Trump children had to come up with money of their own to buy their father’s mortgages. Most were purchased from Fred Trump’s banks by trusts and partnerships that he set up and seeded with money.

Co-op sales, mortgage payments, ground leases — Fred Trump was a master at finding ways to enrich his children in general and Donald Trump in particular. Some ways were like slow-moving creeks. Others were rushing streams. A few were geysers. But as the decades passed they all joined into one mighty river of money. By 1990, The Times found, Fred Trump, the ultimate silent partner, had quietly transferred today’s equivalent of at least $46.2 million to his son.

Donald Trump took on a mien of invincibility. The stock market crashed in 1987 and the economy cratered. But he doubled down thanks in part to Fred Trump’s banks, which eagerly extended credit to the young Trump princeling. He bought the Plaza Hotel in 1988 for $407.5 million. He bought Eastern Airlines in 1989 for $365 million and called it Trump Shuttle. His newest casino, the Trump Taj Mahal, would need at least $1 million a day just to cover its debt.

The skeptics who questioned the wisdom of this debt-fueled spending spree were drowned out by one magazine cover after another marveling at someone so young taking such breathtaking risks. But whatever Donald Trump was gambling, not for one second was he at risk of losing out on a lifetime of frictionless, effortless wealth. Fred Trump had that bet covered.

The Safety Net Deploys

Bailouts, collateral, cash on hand — Fred Trump was prepared, and was not about to let bad bets sink his son.

As the 1980s ended, Donald Trump’s big bets began to go bust. Trump Shuttle was failing to make loan payments within 15 months. The Plaza, drowning in debt, was bankrupt in four years. His Atlantic City casinos, also drowning in debt, tumbled one by one into bankruptcy.

What didn’t fail was the Trump safety net. Just as Donald Trump’s finances were crumbling, family partnerships and companies dramatically increased distributions to him and his siblings. Between 1989 and 1992, tax records show, four entities created by Fred Trump to support his children paid Donald Trump today’s equivalent of $8.3 million.

Fred Trump’s generosity also provided a crucial backstop when his son pleaded with bankers in 1990 for an emergency line of credit. With so many of his projects losing money, Donald Trump had few viable assets of his own making to pledge as collateral. What has never been publicly known is that he used his stakes in the mini-empire and the high-rise for the elderly in East Orange as collateral to help secure a $65 million loan.

Tax records also reveal that at the peak of Mr. Trump’s financial distress, his father extracted extraordinary sums from his empire. In 1990, Fred Trump’s income

 

 exploded to $49,638,928 — several times what he paid himself in other years in that era.

Fred Trump, former employees say, detested taking unnecessary distributions from his companies because he would have to pay income taxes on them. So why would a penny-pinching, tax-hating 85-year-old in the twilight of his career abruptly pull so much money out of his cherished properties, incurring a tax bill of $12.2 million?

The Times found no evidence that Fred Trump made any significant debt payments or charitable donations. The frugality he brought to business carried over to the rest of his life. According to ledgers of his personal spending, he spent a grand total of $8,562 in 1991 and 1992 on travel and entertainment. His extravagances, such as they were, consisted of buying his wife the odd gift from Antonovich Furs or hosting family celebrations at the Peter Luger Steak House in Brooklyn. His home on Midland Parkway in Jamaica Estates, Queens, built with unfussy brick like so many of his apartment buildings, had little to distinguish it from neighboring houses beyond the white columns and crest framing the front door.

There are, however, indications that he wanted plenty of cash on hand to bail out his son if need be.

Such was the case with the rescue mission at his son’s Trump’s Castle casino. Donald Trump had wildly overspent on renovations, leaving the property dangerously low on operating cash. Sure enough, neither Trump’s Castle nor its owner had the necessary funds to make an $18.4 million bond payment due in December 1990.

On Dec. 17, 1990, Fred Trump dispatched Howard Snyder, a trusted bookkeeper, to Atlantic City with a $3.35 million check. Mr. Snyder bought $3.35 million worth of casino chips and left without placing a bet. Apparently, even this infusion wasn’t sufficient, because that same day Fred Trump wrote a second check to Trump’s Castle, for $150,000, bank records show.

With this ruse — it was an illegal $3.5 million loan under New Jersey gaming laws, resulting in a $65,000 civil penalty — Donald Trump narrowly avoided defaulting on his bonds.

Birds of a Feather

Both the son and the father were masters of manipulating the value of their assets, making them appear worth a lot or a little depending on their needs.

As the chip episode demonstrated, father and son were of one mind about rules and regulations, viewing them as annoyances to be finessed or, when necessary, ignored. As described by family members and associates in interviews and sworn testimony, theirs was an intimate, endless confederacy sealed by blood, shared secrets and a Hobbesian view of what it took to dominate and win. They talked almost daily and saw each other most weekends. Donald Trump sat at his father’s right hand at family meals and participated in his father’s monthly strategy sessions with his closest advisers. Fred Trump was a silent, watchful presence at many of Donald Trump’s news conferences.

“I probably knew my father as well or better than anybody,” Donald Trump said in a 2000 deposition.

They were both fluent in the language of half-truths and lies, interviews and records show. They both delighted in transgressing without getting caught. They were both wizards at manipulating the value of their assets, making them appear worth a lot or a little depending on their needs.

Those talents came in handy when Fred Trump Jr. died, on Sept. 26, 1981, at age 42 from complications of alcoholism, leaving a son and a daughter. The executors of his estate were his father and his brother Donald.

Fred Trump Jr.’s largest asset was his stake in seven of the eight buildings his father had transferred to his children. The Trumps would claim that those properties were worth $90.4 million when they finished converting them to cooperatives within a few years of his death. At that value, his stake could have generated an estate tax bill of nearly $10 million.

But the tax return signed by Donald Trump and his father claimed that Fred Trump Jr.’s estate owed just $737,861. This result was achieved by lowballing all seven buildings. Instead of valuing them at $90.4 million, Fred and Donald Trump submitted appraisals putting them at $13.2 million.

Emblematic of their audacity was Park Briar, a 150-unit building in Queens. As it happened, 18 days before Fred Trump Jr.’s death, the Trump siblings had submitted Park Briar’s co-op conversion plan, stating under oath that the building was worth $17.1 million. Yet as Fred Trump Jr.’s executors, Donald Trump and his father claimed on the tax return that Park Briar was worth $2.9 million when Fred Trump Jr. died.

This fantastical claim — that Park Briar should be taxed as if its value had fallen 83 percent in 18 days — slid past the I.R.S. with barely a protest. An auditor insisted the value should be increased by $100,000, to $3 million.

During the 1980s, Donald Trump became notorious for leaking word that he was taking positions in stocks, hinting of a possible takeover, and then either selling on the run-up or trying to extract lucrative concessions from the target company to make him go away. It was a form of stock manipulation with an unsavory label: “greenmailing.” The Times unearthed evidence that Mr. Trump enlisted his father as his greenmailing wingman.

On Jan. 26, 1989, Fred Trump bought 8,600 shares of Time Inc. for $934,854, his tax returns show. Seven days later, Dan Dorfman, a financial columnist known to be chatty with Donald Trump, broke the news that the younger Trump had “taken a sizable stake” in Time. Sure enough, Time’s shares jumped, allowing Fred Trump to make a $41,614 profit in two weeks.

Later that year, Fred Trump bought $5 million worth of American Airlines stock. Based on the share price — $81.74 — it appears he made the purchase shortly before Mr. Dorfman reported that Donald Trump was taking a stake in the company. Within weeks, the stock was over $100 a share. Had Fred Trump sold then, he would have made a quick $1.3 million. But he didn’t, and the stock sank amid skepticism about his son’s history of hyped takeover attempts that fizzled. Fred Trump sold his shares for a $1.7 million loss in January 1990. A week later, Mr. Dorfman reported that Donald Trump had sold, too.

With other family members, Fred Trump could be cantankerous and cruel, according to sworn testimony by his relatives. “This is the stupidest thing I ever heard of,” he’d snap when someone disappointed him. He was different with his son Donald. He might chide him — “Finish this job before you start that job,” he’d counsel — but more often, he looked for ways to forgive and accommodate.

By 1987, for example, Donald Trump’s loan debt to his father had grown to at least $11 million. Yet canceling the debt would have required Donald Trump to pay millions in taxes on the amount forgiven. Father and son found another solution, one never before disclosed, that appears to constitute both an unreported multimillion-dollar gift and a potentially illegal tax write-off.

In December 1987, records show, Fred Trump bought a 7.5 percent stake in Trump Palace, a 55-story condominium building his son was erecting on the Upper East Side of Manhattan. Most, if not all, of his investment, which totaled $15.5 million, was made by exchanging his son’s unpaid debts for Trump Palace shares, records show.

Four years later, in December 1991, Fred Trump sold his entire stake in Trump Palace for just $10,000, his tax returns and financial statements reveal. Those documents do not identify who bought his stake. But other records indicate that he sold it back to his son.

Under state law, developers must file “offering plans” that identify to any potential condo buyer the project’s sponsors — in other words, its owners. The Trump Palace offering plan, submitted in November 1989, identified two owners: Donald Trump and his father. But under the same law, if Fred Trump had sold his stake to a third party, Donald Trump would have been required to identify the new owner in an amended offering plan filed with the state attorney general’s office. He did not do that, records show.

He did, however, sign a sworn affidavit a month after his father sold his stake. In the affidavit, submitted in a lawsuit over a Trump Palace contractor’s unpaid bill, Donald Trump identified himself as “the” owner of Trump Palace.

Under I.R.S. rules, selling shares worth $15.5 million to your son for $10,000 is tantamount to giving him a $15.49 million taxable gift. Fred Trump reported no such gift.

According to tax experts, the only circumstance that would not have required Fred Trump to report a gift was if Trump Palace had been effectively bankrupt when he unloaded his shares.

Yet Trump Palace was far from bankrupt.

Property records show that condo sales there were brisk in 1991. Trump Palace sold 57 condos for $52.5 million — 94 percent of the total asking price for those units.

Donald Trump himself proclaimed Trump Palace “the most financially secure condominium on the market today” in advertisements he placed in 1991 to rebut criticism from buyers who complained that his business travails could drag down Trump Palace, too. In December, 17 days before his father sold his shares, he placed an ad vouching for the wisdom of investing in Trump Palace: “Smart money says there has never been a better time.” 

By failing to tell the I.R.S. about his $15.49 million gift to his son, Fred Trump evaded the 55 percent tax on gifts, saving about $8 million. At the same time, he declared to the I.R.S. that Trump Palace was almost a complete loss — that he had walked away from a $15.5 million investment with just $10,000 to show for it.

Federal tax law prohibits deducting any loss from the sale of property between members of the same family, because of the potential for abuse. Yet Fred Trump appears to have done exactly that, dodging roughly $5 million more in income taxes.

The partnership between Fred and Donald Trump was not simply about the pursuit of riches. At its heart lay a more ambitious project, executed to perfection over decades — to create that origin story, the myth of Donald J. Trump, Self-Made Billionaire.

Donald Trump built the foundation for the myth in the 1970s by appropriating his father’s empire as his own. By the late 1980s, instead of appropriating the empire, he was diminishing it. “It wasn’t a great business, it was a good business,” he said, as if Fred Trump ran a chain of laundromats. Yes, he told interviewers, his father was a wonderful mentor, but given the limits of his business, the most he could manage was a $1 million loan, and even that had to be repaid with interest.

Through it all, Fred Trump played along. Never once did he publicly question his son’s claim about the $1 million loan. “Everything he touches seems to turn to gold,” he told The Times for that first profile in 1976. “He’s gone way beyond me, absolutely,” he said when The Times profiled his son again in 1983. But for all Fred Trump had done to build the myth of Donald Trump, Self-Made Billionaire, there was, it turned out, one line he would not allow his son to cross.