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Trump Tax Revelations No Surprise to Past Associates

When Sebastian Pignatello saw the news that Donald Trump had declared a loss of $916 million in 1995, potentially allowing him to legally avoid paying federal income taxes for close to two decades, the retired Queens investor wasn’t surprised. As a shareholder in the Trump Hotels and Casino Resorts, Pignatello had a front row seat to the many ways in which he says Trump used the legal and corporate landscape for his own benefit, almost always at the expense of everyone else's.

“I invested in the Trump casinos because I thought there was value there,” said Pignatello, 67. “What I was totally oblivious to was Donald Trump’s ability and willingness to screw the people that he deals with... That was my downfall as an investor.”

Trump: I Have 'Brilliantly' Used Tax Laws to My Benefit 0:48

For the general public, Trump’s 1995 tax records, reported Saturday by the New York Times, offered a rare glimpse into the financial standing of the Republican nominee -- the first presidential candidate since 1972 to decline to release any of his tax returns.

They showed a man who appeared able to reap extraordinary tax benefits from his own financial blunders in the early 1990s -- including three Atlantic City casino bankruptcies, a failed airline business and a poorly-timed purchase of Manhattan’s Plaza Hotel.

But for at least a portion of those who’ve done business with Trump in the past, watching him make money while they’ve lost, the 1995 documents affirmed something about the candidate that they already knew: Trump is in it for Trump, and no one else.

“The man makes money no matter what,” said Marty Rosenberg, 73, who says his plate glass company lost hundreds of thousands of dollars when Trump’s Taj Mahal went bankrupt in 1991. “That’s all that’s important to him. That and his ego.”

Rosenberg’s company, Atlantic Plate Glass, was nearly finished with its work on a multi-million dollar contract with the Taj Mahal when he says payments suddenly stopped. He was owed about $1.2 million, he said.

Rather than accept the losses, Rosenberg organized a group of subcontractors who were owed money for work on the casino and set out to negotiate with Trump’s attorneys.

Rosenberg was able to recoup a portion of the money left on his contract, but he still took a hit. He knew others weren’t as lucky.

"Did we survive? Absolutely," he said. "But there were a lot of people who didn't."

That feeling is shared by retired music store owner Michael Diehl, who says he lost $30,000 — or about a third of his yearly income -- on a $100,000 contract to supply the Taj with grand pianos. The 89-year-old said the gambling mecca could only give him 70 cents on the dollar when it ran into financial difficulties prior to declaring bankruptcy in 1991.

“I don’t think Donald Trump could walk down the boardwalk in Atlantic City without looking around behind his back to see who’s after him,” said Diehl. “Because some people are really, really upset. They’ve lost hundreds of thousands of dollars. I got off easy.”

Trump Contractors: 'It Was the Beginning of the End for Us' 2:57

Throughout the campaign, Trump has bragged about his business record, framing six bankruptcies -- as he did in last week’s debate -- as “us[ing] certain laws that are there.” At the debate, he also brushed off an accusation of not paying federal income taxes by saying, “That makes me smart.”

But the 1995 tax records shed new light on the extent to which Trump possibly used existing laws to his advantage, even while others suffered by his hands.

In 1995, the provision that may have been working in Trump’s favor is known as net operating loss, or N.O.L. -- a tax deduction that occurs when business expenses exceed gross income. Essentially, N.O.L allows for business losses to flow onto the personal tax returns of individuals like Trump, canceling out taxable income.

Tax experts consulted by The Times said the $916 million N.O.L declared by Trump in 1995 almost certainly included large losses carried over from the early 1990s, when most of Trump’s key businesses were floundering and hurting people like Diehl and Rosenberg.

“These tax laws are favoring to the super-wealthy,” said Rosenberg. “It is what it is. It’s legal.”

Though Pignatello did not go into business with Trump until years later, he says he saw a similar pattern of behavior whereby Trump would game the system to come out on top, burying everyone else.

“The casino industry was healthy,” said Pignatello, explaining his decision to invest in the Trump Hotels and Casino Resorts, which went bankrupt in 2004. “He was pillaging the company. He was making dumb decisions. He was self-dealing.”

Pignatello recalled Trump charging the casinos hundreds of thousands of dollars for Trump-brand water that waiters passed out for free on the floor. He says he was also charging the casinos four times the going rate for a Trump helicopter to fly high rollers from New York to Atlantic City. The New York Times previously reported the large sums the casinos spent on “Trump labeled merchandise.”

When the company went bankrupt, Pignatello served as a member of the shareholders’ committee that tried to recover losses. Even then, he was stunned to see Trump taking advantage of another provision: the prepackaged bankruptcy, which allows the debtor to agree in advance to the terms of reorganization with its creditors.

“It’s a code word for, ‘We’re going to get our way and screw everybody else,’” said Pignatello. “He knew exactly how to manipulate the system.”

As part of the prepackaged bankruptcy, Trump walked away with a personal stake in the Miss Universe pageant, which the casinos owned. He also got to stay on as chairman of the board with a $2 million-a-year salary.

Shareholders sued, saying the reorganization deal would bestow “a basket of goodies” on Trump. In the end, Trump Hotels and Casino Resorts agreed to pay $17.5 million to stockholders, as well as the proceeds from the sale of land that had been earmarked for Trump under the original reorganization plan.

The Trump campaign did not respond to NBC News' request for comment on the claims of Rosenberg, Pignatello and Diehl.

However, in a statement to The Times regarding the 1995 tax documents, the campaign insisted that the candidate “has paid hundreds of millions of dollars in property taxes, sales and excise taxes, real estate taxes, city taxes, state taxes, employee taxes and federal taxes.” The campaign also noted that Trump has “a fiduciary responsibility to his business, his family and his employees to pay no more tax than legally required.”

The statement, more so than what the 1995 tax documents revealed, made Pignatello’s jaw drop.

"During his time that he was chairman of the casinos... the last thing on his mind was fiduciary responsibility," said Pignatello. "He probably belongs in jail for his breach of fiduciary responsibility."

Pignatello warned Trump’s supporters to expect more of the same if he wins in November.

"If these people think he's going to use his business skills and negotiating skills to help them, they're in for a rude awakening,” he said. “Trump’s in this for himself."