In a recent story published in the New York Times, selected sections of Trump’s tax returns in 1995 showed he registered a $916 million loss that year. As a result, this would enable him to avoid any payment of personal income taxes on his returns for up to 18 years.
Critics of the strategy have been vocal because many see this as a potential deciding factor for independent voters. Politico reported that while supporters approved of the strategy, detractors point to the massive loss as proof that either Trump’s business ventures have not been as successful as he reported, or that he has hidden assets and did not pay an adequate share of individual income taxes.
Furthermore, critics have been outspoken about the fact that by Trump not publicly releasing his financial records, he is withholding the identity of debtors and creditors who could have influence over his campaign. This could leave the door open to special interest groups guiding some of Trump’s policies as president. Ultimately, this could tarnish his position as a self-made business success to his voter base.
Supporters approve of the Trump tax strategy
Those in favor of Trump’s tax avoidance strategy point to his prowess as a businessman. They also assert that the manner in which he has minimized his individual tax return is well within the legal application of the IRS tax codes.
Supporters have additionally been on record to state that his individual tax returns should be withheld because he is not a public official. In fact, former New York City mayor Rudy Giuliani argued recently that not releasing these records is part of a fiduciary obligation:
“You are ignoring completely the fiduciary obligation that he has to all the people around him to run his business at the lowest possible expense,” Giuliani explained.
Whether Trump’s strategy is part of a fiduciary duty to his shareholders is still up for debate. However, it remains to be seen if him taking the loss on his individual income tax returns is part of this fiduciary obligation. The impact of this revelation could be significant come election day for those both in favor and against the tax minimization strategy.
Supreme Court and Title VII: Implications for Reverse Discrimination
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Special purpose acquisition companies (better known as SPACs) appear to be making a comeback. SPAC offerings for 2025 have already nearly surpassed last year’s totals, with additional transactions in the pipeline. SPACs last experienced a boom between 2020–2021, with approximately 600 U.S. companies raising a record $163 billion in 2021. Notable companies that went public […]
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Tariff Response Options for Small Businesses Facing Financial Distress
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Common Causes of Partnership Disputes and How to Resolve Them
Business partnerships, much like marriages, function exceptionally well when partners are aligned but can become challenging when disagreements arise. Partnership disputes often stem from conflicts over business strategy, financial management, and unclear role definitions among partners. Understanding Business Partnership Conflicts Partnership conflicts place significant stress on businesses, making proactive measures essential. Partnerships should establish detailed […]
Businesses Are Facing Financial Headwinds—A Practical Guide
*** The original article was featured on Bloomberg Tax, April 28, 2025 — As a tax attorney who spends much of my time helping people and companies who have large, unresolved issues with the IRS or one or more state tax departments, it often occurs to me that the best service that I can provide […]
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