Trump’s tax returns suggest that his businesses are perennial money-losers, while raising questions about how he manages to finance a gilded lifestyle. For each of the six years from 2015 through 2020, one of Trump’s main business entities, DJT Holdings, lost millions of dollars. The smallest loss was $34 million in 2015. The largest was $64 million in 2016. Combined, those losses total $314 million from 2015 through 2020. Shrewd!