The story of Trump’s business career, his taxes and his debt

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  • A bombshell New York Times report claims that Trump paid only $750 in federal income taxes in 2016, and nothing at all for much of the previous decade, a major contrast with his image as a self-made billionaire.
  • Trump’s business career shows a series of flashy and ambitious investments that go bust, sometimes ending in bankruptcy, with Trump moving on from the wreckage each time.
  • Multiple reported windfalls throughout Trump’s career — from inheriting millions as a child to the millions he began earning as a reality-TV star from ‘The Apprentice’ — have given major boosts to Trump’s investments over the decades.
  • Another windfall arguably came in 2016, when Trump was elected president.
  • Visit Business Insider’s homepage for more stories.


Visiting my grandmother in Queens in the late ’80s and early ’90s meant a few things.

There were the M&M’s she always had laying out on her coffee table, usually next to her daily copy of New York Post. There was a haze of cigarette smoke from the Parliaments she was always smoking, and, somewhere in the ether, there was mention of Donald Trump.  

He was everywhere in the tristate area in those years, long before NBC’s “The Apprentice” made him a national figure. His name blanketed the Post’s gossipy Page Six and the buildings up and down I-95, from Atlantic City to Central Park West. 

By the turn of the ’90s, a string of corporate bankruptcies meant that Trump’s name migrated from the sports and gossip pages to other sections of the paper. This set in motion a long-running series of reports on Trump business failures that may have culminated with the New York Times’ bombshell from this weekend. Tax records show Trump claimed chronic losses for much of the last decade, per the Times, leading to just a