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Donald Trump New York City Press Launch For Latest Venture Trump Mortgage LLC
Nearly a decade ago, just before the housing crisis, Donald Trump launched Trump Mortgage LLC.
Jemal Countess—WireImage/Getty Images

The "Trump" name has appeared in quite a few businesses. It's been on skyscrapers, hotels, a failed airline, a Virginia winery, a golf course built on a landfill, and a sketchy "university," to name a few. Among the Trump businesses that have gone belly up is Trump Mortgage, LLC which had a brief life starting in 2006, just before the housing crisis.

Recently, John Oliver and others have battered around this defunct mortgage company as indicative of a lack of financial savvy on the behalf of Donald Trump--and a preview of how he might make decisions as a president.

“Starting a mortgage company in 2006 was one of the worst decisions you could possibly make,” said Oliver, on his show "Last Week Tonight with John Oliver."

Back in 2006, Trump introduced the mortgage branch, gave it prominent branding on his website, and told CNBC it was a great time to start a mortgages company. "The real estate market is going to be very strong for a long time to come,” Trump said at the time.

But as anyone who's seen or read "The Big Short" or lived through the '00s knows, this was not the case. In fact, that was probably the worst time to start a mortgage company and invest in the housing market.

Trump points to his business acumen as a prime reason for why he would be a good president, and yet epic failures like Trump Mortgage show that he may not be quite as brilliant a businessman as he makes himself out to be. Many have debated whether Donald Trump's reputation as a successful business man is deserved. Despite all the branding and activity, a lazy Trump would have been richer by a few billion dollars if he had quit the real estate business in 1982, put his money in an index fund, and played out his days on the golf course instead of his real life game of Monopoly, according to a Vox analysis.

Read next: 8 Epic Business Failures with Donald Trump's Name on Them

The Trump Mortgage is an especially damning failed venture, the Washington Post noted this week, because Trump decided to wave off the concerned voices of experts whispering "bubble" in 2006: "His decision to embrace the mortgage business illustrates the potential dangers of a business philosophy that has relied in part on a willingness to put aside the advice of experts and take risks," the story explained.

Besides starting a company in the face of concerns about the housing bubble, Trump publicly decried prognostication at the time, saying he didn't believe in it. He also cited his Wharton School undergraduate education as the reason for his understanding of the issue, according to the Post.

All this has painted Trump—in mainstream and conservative media alike—as a brash man with a penchant for playing chicken and disavowing the insights of experts, which is not likely to be considered a desirable trait in a president, who carries the codes to a nuclear arsenal.