The U.S. tax code has long given entrepreneurs a break for taking risks and losing money.
But, in 1995, GOP presidential candidate Donald Trump apparently took that idea to an entirely new level.
On Sunday, The New York Times reported that Trump converted nearly a billion dollars in business losses — from failed ventures in casinos, real estate and a now defunct regional airline — to win a free pass with the IRS with the potential to shield as much as 18 years of his personal income from taxes.
The newspaper said it anonymously received the first pages of Trump's 1995 state income tax filings in New York, New Jersey and Connecticut. The filings, confirmed as authentic by the accountant who prepared them, show a net loss of $915,729,293 in federal taxable income for the year.
Millions of Americans over the years have applied business losses to offset personal income. The provision is intended to encourage people to start new businesses or expand existing ventures by investing in new equipment or hiring more workers.
But like many of his personal, professional and political claims, the size of Trump's 1995 net operating loss was off the charts.
A CNBC review of IRS tax return data found that in 1995 claims of net operating losses averaged about $98,000 per return. At $916 million, Trump's net operating loss in 1995 was more than 9,000 times the average amount claimed that year.