It's the 1980s and just like the rest of America, Donald is going big. Against his father's advice Donald plunges into the casino business. He goes on a mega spending spree that includes a yacht, an airline, a helicopter and an American football team. He's also at the top of the best-selling book chart, with The Art of the Deal. Featured in this episode are Tony Schwartz, the ghost writer behind the book, and Mike Dunbar, who first suggested in 1987 the idea of Donald Trump becoming President. But as the decade closes Donald's life is starting to unravel. His marriage to Ivana falls apart due to an affair with Marla Maples, and the 1989 stock market plummet results in his loans on the assets he has bought overwhelming him. Donald runs out of cash, has to sell major parts of his empire and seeks help from the only person who can discreetly bail him out: his father.

Pop culture permeates politics at the turn of the millennium. Pro-wrestler Jesse Ventura becomes governor of Minnesota and Trump is eager to learn from his campaign. Trump's spending is once again out of control; he's overpaying for everything and becoming the punchline of many a joke. Enter tall, beautiful model Melania Knauss. The playboy is reined in and Donald is tenacious and inspired. He's in his late 60s and ready to take residence in the one piece of American real estate that money allegedly cannot buy: The White House. Interviews with political advisor Dean Barkley and seasoned presidential mentor Roger Stone reveal the atmosphere as Donald dips his toe into the presidential pool, toying with reform party candidacy. George Bush Jr. is president and American society is crumbling at the turn of the millennium.