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As of May, 2019, Trump's Doral resort in Miami, previously the most money-making property in the Trump Organization, had seen its net operating income decline by 69 percent from 2015 to 2017, or from $13.8 million to $4.3 million. The resort in Miami is not his only property that is losing money.
His golf course in Scotland is hemorrhaging money as well, but is being kept afloat by the Air Force, which refuels at a nearby airport. The Trump Tower in New York has been wracked by financial woes over the last two years. The occupancy rate in the building had fallen from 99% to 83%, and the majority of condos in the building had sold at a loss.
"No one wants in that building," Michael Sklar, a former Trump Tower condo owner, told Bloomberg.
Another big surprise, though, is the Trump Tower in Chicago. From 2015 to 2018, profits at the location fell 89%, from $16.7 million to $1.8 million, according to documents filed in Cook County, Illinois.
The decade of the 1980's were also a tough time for "the stable genius" since he managed to lose over $1 billion from 1985 to 1994. Over all, Mr. Trump lost so much money that he was able to avoid paying income taxes for eight of the 10 years. It is not known whether the I.R.S. later required changes after audits.