I have no sources of information that are not currently public. I am only speculating as an interested political voyeur. But consider his reported losses in 1995. And I recall from loosely following his career since the '70s, that he took huge personal hits earlier. And what would later tax returns show? Can we assume that the nearly billion dollar loss in 1995 is his only massive loss? No, we can't. Losses of that magnitude involve serious and often nasty players in the debt market. Is he still indebted from his failed real estate dealings? A fair question, I would think. Assuming that he does have continuing creditors, who and where are they? Recall his comments that he is the "King of debt." He did not say "was", he said "is." And consider the that the New York Attorney General has just ordered his "charitable foundation" to cease soliciting funds from others, and reporters have uncovered that he last made a personal contribution to that fund back in 2008. And if he is truly financially independent, what, many have asked, is his reason for running for president of the United States? Gosh, why am I reminded here of the saying: Follow the money.
It appears that real estate developers can have very large losses while actually being profitable thanks to our tax code. CNBC was reporting some of these details. The Dems cherry picked this one aspect of his taxes because they know most people don't have a clue about carry forward losses in a business. The spin about avoiding taxes works quite well because most people can't balance their own checkbook much less understand that he was just doing what the tax code allowed thanks to our Congress.