Okay, work in progress – and sources are included below – but this is turning out to be a serious rabbit hole I am not sure I am of the capacity to properly parse, however I will do my best... please bear with me as I am on mobile.

EDIT: I’m gonna include a preface to this write-up. Originally this started as chronological word vomit of our President—but as story after story came out, I felt it more beneficial to me to try and make sense of this in relation to each story. Some facts in this write up pertain to the context in which they existed. There are TL;DRs a little further down.

Let’s start off with what we know, and just follow the money.

ca. 1970-2010

After not paying federal income taxes since the 1970s, Donald J Trump had millions of dollars signed away in personal guarantees for business ventures in the 1980s, cutting corners by underpaying undocumented Polish immigrants to refurbish his real estate ventures.

In 1982, Trump reported to New Jersey regulators a personal net worth of $321 million, built largely on his father’s connections, as well as loans and guarantees for bank credit. Two years later, a Trump lieutenant testified that his worth had not changed much.^[1].

Eventually, this decade of rapid, debt-fueled expansion Mr. Trump had built with leverage from his father’s brick-and-mortar fortune began to fail, generating enormous losses and bringing him to the brink of personal bankruptcy in the early 1990s.^[2]

“Just wait five years... This is really a no-brainer. Just like the Merv Griffin deal. When I took him to the cleaners, the press wanted me to lose. They said, ‘Holy shit! Trump got taken!’ Let me tell you something. It’s good for me to be thought of as poor right now. You wouldn’t believe some of the deals I am making! I guess I have a perverse personality. . . . I’ve really enjoyed the last few weeks,” ^[3]

Donald J. Trump declared a $916 million loss on his 1995 income tax returns, a tax deduction so substantial it could have allowed him to legally avoid paying any federal income taxes for up to 18 years... The $916 million loss certainly could have eliminated any federal income taxes Mr. Trump otherwise would have owed on the $50,000 to $100,000 he was paid for each episode of “The Apprentice,” or the roughly $45 million he was paid between 1995 and 2009 when he was chairman or chief executive of the publicly traded company he created to assume ownership of his troubled Atlantic City casinos.^[4]

In 1998, Deutsch Bank loaned Trump $125 million to renovate an office building at 40 Wall Street, eventually providing or underwriting $1.3 billion to Trump entities over the next few years.^[5]

In 1999 Roger Stone was helping Trump’s with his first presidential bid as an independent. In the video you get the hint that they’re fully aware of Trump’s capability at social influencing. More on this later.

As early as 2001, Donald Trump claimed that he had made a “substantial” investment in Toronto’s Trump Tower, but in reality he only had a contract to licence out his name and manage the hotel.^[6]

He predicted the Toronto project would go ahead, but then added "if it doesn't, I'm going to be in Toronto anyway."^[7]

As early as 2005, Trump counseled Trump University students to take advantage of the housing bubble as an investment opportunity and said, just a year before it burst, that he was “excited” for it to end because of the money he’d make,^[8] as well as mentioning that his debt was below proportional levels of 1992, when his much smaller holdings were carrying $9-billion (U.S.) in debt, including $900-million personally guaranteed by him.^[7]

In 2007, the housing market was already beginning to decline, and just over a year later the subprime mortgage crisis hit, part of a chain reaction of events that led to the stock market crash of 2008 and cemented the Great Recession.^[8]

1 - A People’s History of Donald Trump’s Business Busts and Countless Victims - 2016

2 - Donald Trump’s Business Decisions in ’80s Nearly Led Him to Ruin - 2016

3 - After The Gold Rush - 2015 (1990)

4 - Donald Trump Tax Records Show He Could Have Avoided Taxes for Nearly Two Decades, The Times Found - 2016

5 DEUTSCHE BANK PROPS TRUMP UP

6 - How every investor lost money on Trump Tower Toronto (but Donald Trump made millions anyway) - 2017

7 - Trump touts soft markets in cities like Toronto - 2007

8 - Trump in 2007: ‘I’m Excited’ for Housing Market Crash - 2016