As every day of Donald Trump's presidential campaign seemingly generates new headlines, this two-hour special examines the increasingly polarizing candidate's past. Included is rarely seen footage from Trump's interviews with Phil Donahue and his comments about politics from the floor of the 1988 Republican convention. Additionally, celebrities, politicians, and people described as "close to The Donald" weigh in, including former US Senator Al D'Amato (R-N.Y.), former Atlantic City mayor Jim Whelen, boxer Mike Tyson, and notorious "Apprentice" contestant Omarosa.