When Ivanka Trump Opened Up About Donald's Massive Debt: 'I Remember My Father...'

In 2019, Samantha Bee of TBS's Full Frontal showed a scene from the 2003 documentary Born Rich, in which Ivanka Trump recounted an anecdote about Donald Trump's hard financial times by pointing to a homeless person. The man behind Born Rich, Jamie Johnson, is an heir to the Johnson & Johnson company. For several years, he filmed other millionaires to see how they dealt with inheriting money, and a clip from this documentary grabbed everyone's attention because of a particular anecdote the younger Trump shared.

Ivanka recounted how in her childhood when she was nine or ten years old, she was strolling down Fifth Avenue with her father shortly after he separated from her mother, Ivana Trump. Next to Trump Tower, they saw a guy who seemed to be homeless. As reported by HuffPost, she recalled at the time, "I remember my father pointing to him and saying, ‘You know, that guy has 8 billion dollars more than me,’ because he was in such extreme debt at that point." Nonetheless, she expressed her pride in her parents for successfully navigating that situation.

However, Bee was not as appreciative of the GOP frontrunner as his own daughter. She claimed, "Look, the only thing that Donald Trump really had going for him as a candidate was that he was supposed to be a great businessman. Now we know that not only is he a bad businessman, he is one of the worst in American history."

According to an article in the New York Times that came out the same year, based on IRS documents, Donald's companies lost approximately $1.2 billion from 1985 to 1994. Moreover, between 1990 and 1991, his company lost almost $250 million, which was more than double that of the nearest taxpayer for those two years. Even though it remained uncertain if the IRS requested him to make adjustments during audits, the records showed that he lost so much money that he evaded paying income tax for eight of the ten years.

At the time of this article's publication, tensions were rising between the Trump administration and House Democrats over the Democrats' demand for the former President's 2013–2018 tax returns, both personally and for his businesses. While the outlet did not have Donald's actual tax returns for the years 1985 to 1994, they did get transcripts of his taxes for those years, which included numbers from his federal returns. A copy of the former President's state tax returns from 1995, which revealed a deficit of over $900 million, was covertly sent to the Times during the 2016 election.

The publication also discovered that between 1986 and 1988, Donald amassed millions of dollars by buying stock, implying he would seize control of the firms to boost their prices, and then subsequently sell the shares. He lost most, if not all, of the advantages he had made in this manner, according to the Times. The former President's parents' estate and gift taxes were minimized in the 1990s using 'dubious' tax strategies in which Donald and his family participated.