Trump businesses reportedly lost more than $1 billion over a decade A new report claims President Trump's businesses were bleeding red ink while he bragged about "The Art of the Deal." The New York Times looked at IRS tax transcripts and information from the president’s tax forms and found more than $1 billion in losses from 1985 to 1994. He lost so much money, he did not pay income taxes in eight of those 10 years. Weijia Jiang reports.