Friedrich Drumpf. Donald Trump's grandfather was born Friedrich Drumpf in 1869 in Germany. He emigrated to the US when he was sixteen, worked as a barber for six years then moved to Seattle where he appears to have changed his name to Trump, then later to Monte Cristo, Washington, Bennet, British Columbia, and Whitehorse, Yukon. In those location he had a series of restuarants and hotels that served food and liquor and had prostitutes.
He returned to Germany where he married Elisabeth Christ. Because Drumpf had failed to serve in the German military he was stripped of his German citizenship. He returned to the United States opening restuarants in New York City. Towards the end of his career he had started being engaged in real estate business.
Fred Trump. Donald Trump's father Fred Trump expanded the real estate operations of his father, and was very succesful in selling garages after World War II, and then middle class housing. Fred taught Donald the real estate business, helped him make political connections in New York City, and helped him by providing $1 million to get started. When one of Donald's casinos was failing Fred bought $3.36 million of chips that he never used, effectively providing additional financing. The New Jersey Division of Gaming Enforcement found that the loan was illegal and Trump eventually paid a $30,000 fine.
Fred obtained a license to provide additional funding for subsequent loans which were made and paid off.
Fred Trump was arrested in conjunction with a Ku Klux Klan event in Queens in the 1920's, and shared lawyers with the men charged with attacking police officers at the Klan "parade."
Folksinger Woody Guthrie who wrote the famouos folk song "This Land is Your Land," was a tenant in one of Fred Trump's apartments following World War II. These are two songs he wrote about Fred and the racially segregated apartments:
Fred died in 1999 leaving a fortune estimated to be $250 to $300 million.
(1) Reporter, "How the Trumps struck Klondike gold: Donald's grandfather gave birth to family's glittering empire with seedy restaurant catering to loose-moralled men and women seeking their fortune," DailyMail.com, Sept. 7, 2012, http://www.dailymail.co.uk/news/article-2200169/How-Trumps-struck-Klondike-gold-Donalds-grandfather-gave-birth-familys-glittering-empire-seedy-restaurant-catering-loose-moralled-men-women-seeking-fortune.html
(2) Wes Williams, "Trump's Immigrant Grandfather Made His Money from Prostitution, Booze and Stealing Land," IfYouOnlyHadNews.com, Sept. 19, 2015, http://www.ifyouonlynews.com/politics/trumps-immigrant-grandfather-made-his-money-from-prostitution-booze-and-stealing-land/
(3) Interview with Gwenda Blair, author of two books about Trump and his family, "What Donald Trump Learned from his German grandpa Friedrich Drumpf," DW.com, Sept. 9, 2015, http://www.dw.com/en/what-donald-trump-learned-from-his-german-grandpa-friedrich-drumpf/a-18701551
(4) Wiki.eanswers.com, Frederick Trump, http://wiki.eanswers.com/en/Frederick_Trump?ext=t&cid=5083
(5) Andrew Kaczynski, "Trump's Other Small Loan from Daddy-O: A Few Millioin Bucks To help Pay Off His Debts," BuzzFeed.com, Oct. 26, 2015,http://www.buzzfeed.com/andrewkaczynski/you-can-rely-on-the-old-mans-money#.ksx8ZKJx7K
(6) Rob Beschizza, "Donald Trump confirms, then denies, his father's arrest at a KKK rally," BoingBoing.net, Sept. 23, 2015,http://boingboing.net/2015/09/23/donald-trump-confirms-then-de.html
(7) Jason Horowitz, "In Interview, Donald Trump Denies Report of Father's Arrest in 1927," New York Times, Sept. 22, 2015,http://www.nytimes.com/politics/first-draft/2015/09/22/in-interview-donald-trump-denies-report-of-fathers-arrest-in-1927/?_r=0
(8) Katie Reilly, "Woody Guthrie Wrote Angry Songs About Donald Tump's Dad," Time, January 21, 2016, http://time.com/4188991/woody-guthrie-donald-trump-fred-trump-songs/