Which transactions in Trump’s returns have been cited by tax experts as unusual or potentially subject to further investigation?
Executive summary
Tax experts singled out a handful of patterns and specific entries in Donald Trump’s released tax returns as unusually aggressive or in need of closer scrutiny—most notably persistent, large net operating losses carried forward; unusually low federal income tax payments in 2016–17; large consultant or “related‑party” payments that look atypical; odd classifications of property to claim deductions; and curious bookkeeping oddities in small subsidiaries that suggest sloppy or suspicious math [1] [2] [3]. Specialists caution that returns alone cannot determine illegality and that full audits would be required to confirm whether any of those items reflect tax evasion or merely aggressive tax planning [3].
1. Persistent carried‑over losses and unusually low tax bills
Multiple tax scholars flagged the scale and longevity of losses Trump reported—hundreds of millions in carryovers that depressed taxable income for years—and noted that those losses, and the resulting tiny federal bills of $750 in 2016 and 2017 and no federal income tax in many earlier years, are highly atypical for someone living at a billionaire standard of living and merit verification by auditors to confirm correct application of net operating loss rules [1] [2] [3].
2. Large related‑party/consulting payments, including to family members
Experts called attention to seven‑figure “consulting” fees reported paid to close associates or family members—most notably payments reported that could be tied to Ivanka Trump—that would be uncommon for an executive actively running a company if no real services were demonstrably performed; specialists said such related‑party payments can be legitimate but also are a classic red flag for tax agencies when they appear to shift income to lower‑tax recipients or mask compensation [1].
3. Real‑estate classifications and charitable deduction claims
Tax specialists highlighted entries where a New York estate was treated as an investment property rather than a personal residence, a classification that enabled larger tax deductions—an approach experts said was unusual given Trump's documented personal use and therefore a plausible subject for IRS challenge if substantiation is lacking [1].
4. Specific large losses and “large, unusual, questionable” items flagged by agents
Congressional reviewers and former IRS officials pointed to particular line items including a $12.1 million loss from the Trump Corp. and the Joint Committee on Taxation’s concern about $105 million in losses claimed on a 2015 return that were carried forward and possibly misapplied—items the committee said warrant verification because mis‑carried losses change tax liabilities in later years [3].
5. Small‑scale math oddities and bookkeeping red flags
Beyond headline losses, academics noted strange bookkeeping in small entities—such as an aviation LLC reporting exactly equal sales and expenses for the same dollar amount in 2020—which taxation experts described as “fishy looking stuff” because exact matches and sloppy arithmetic are atypical and can signal either careless accounting or deliberate smoothing to zero out taxable income [2].
6. What an audit would test and the limits of public returns
Experts repeatedly emphasize that returns raise questions but do not prove wrongdoing; audits (which can examine source documents, contemporaneous contracts, invoices and related‑party agreements) are the tools that would determine whether deductions, classifications and payments were legally claimed or improperly used to avoid tax—an important caveat in publicly released analyses of the returns [3].
7. Political and legal context that colors interpretation
The debate over these items unfolded amid prosecutions, a later guilty plea by an IRS contractor who leaked returns, and Trump’s litigation accusing the IRS and Treasury of harm from the leaks—details that both heighten scrutiny and create incentives for partisan framing of the tax reporting; sources include news reports of the leak case and Trump’s $10 billion lawsuits against agencies he oversees [4] [5] [6] [7] [8].