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https://www.bloomberg.com/features/2016-trump-family-fortune/
Full article at link. Unlike the Kennedy / bootlegging rumours, this is actually true. (Though I remember reading that Joe Kennedy was proven to have done something much worse than bootlegging, but I don't remember what.)
Trump’s Family Fortune Originated in a Canadian Gold-Rush Brothel
“I would advise respectable women travelling alone, or with an escort, to be careful in their selection of hotels at Bennett,” according to a letter penned by “The Pirate” in the Yukon Sun on April 17, 1900. For single men, the Arctic offered excellent accommodations but women should avoid it “as they are liable to hear that which would be repugnant to their feelings and uttered, too, by the depraved of their own sex.”
Trump quickly saw where the real profits lay amid the gold-rush frenzy. An estimated 100,000 prospectors set out for the Klondike, of which only a third actually made it, and a mere 4 percent ever struck gold. Given those odds, Trump’s willingness to lay down his pick was “a shrewd move," according to Blair. “He was mining the miners.”
Bennett was a key hub for prospectors, who trudged from Alaska across frozen mountains and floated rickety rafts down the treacherous rapids of the Yukon River to Dawson City in search of elusive gold. The town lost its allure with the construction of a railway link from Skagway, Alaska to Whitehorse, allowing miners to bypass Bennett.
In response, Trump dismantled the restaurant and its precious lumber and rebuilt it in Whitehorse. A photo in Blair’s book shows a mustachioed Fred Trump in a white apron. He’s standing at the bar near a wall of drapes behind which women, known as “sporting ladies,” entertained miners in privacy.
Trump was a rich man when he left Whitehorse in 1901 to return to his native Kallstadt, Germany, where he later deposited savings of 80,000 marks in the village treasury, Blair recounts. Unable to regain German citizenship, he returned to New York with his riches. That amount—equivalent in purchasing power to about half a million euros in 2014—ended up funding the Trump family’s first residential real estate investments in the New York area, later carried on by his son Fred and grandson Donald.
Full article at link. Unlike the Kennedy / bootlegging rumours, this is actually true. (Though I remember reading that Joe Kennedy was proven to have done something much worse than bootlegging, but I don't remember what.)