According to
a Tuesday column by Lee Sheppard in the tax industry publication Tax Notes, Trump may have benefited greatly in the 1990s from a tax loophole related to forgiven debts - a loophole that would have allowed him to deduct business losses on his personal income tax return, even if those losses were actually borne by banks that loaned Trump money and never got it back.
People often use "loophole" to refer to tax deductions they don't like, but this one was a loophole in the true sense of the word: a tax break created by legislative accident.
This loophole was the subject of
a 2001 Supreme Court case, Gitlitz v. Commissioner, in which the IRS argued the relevant tax law could not have possibly meant what it appeared to say, which was that business owners could in some cases deduct losses they had not actually borne.
After the IRS lost that case, the loophole was closed by the
Job Creation and Worker Assistance Act of 2002, a bill that then Sen. Hillary Clinton voted for and President George W. Bush signed. But that law only stopped taxpayers from using the loophole going forward; they were still allowed to benefit from tax losses they had booked through it in prior years, such as 1995.