I think the word "once" in the thread title is very significant. Trump surely goes back 30+ years in all his wheeling and dealing, and there were many of the nation's 'rich' in 1987 who had no income, due to capital losses, and thus they owed no income taxes. But this is a common tactic of democrats/socialists to bring these things up, especially going back to 'once' or maybe even twice, like 2008 perhaps.
One of those who had no income that year ['87] was Clayton Williams, the west Texas oil man and banker, running against Ann Richards for Governor of Texas. The tactic worked for his defeat after he had the election all the way-- but not that alone. He may have deliberately blown it-- I'll never know. But in addition to declaring he had no income and therefore no taxes-- which straddling voters don't like to hear, be it true or not-- he invited some of the media to come as he and his guys went went off into his remote sections for roundup, and he joked about being "serviced" by hookers, and something about rape-- 'if it's inevitable, you may as well enjoy it'-- and finally, when he and the Wicked Witch of the West [Richards] were on the same stage, he angrily confronted her, saying, "Ann-- I came to call you a liar!" I don't know if her tears were faked or real, but all this combined did work to get WWW elected..
Okay-- the above has almost nothing to do with the current POTUS campaign, except it's not impossible that Trump may be reflexive of Williams in that race. He actually got the nomination, but [arguably] finally got honest with himself that he didn't want to be dogged down continually with business other than his own-- it's running that's the really the thing.
One more little piece of comedy on this. Shortly after the governor's race (months after Desert Storm), there was a cartoon featuring Saddam Hussein at a mirror, saying "Mirror, mirror, on the wall, whose the dumbest leader of all?" Then he taps an associate and says, "Who's Clayton Willilams?"
