
Plot
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.
Trailer
Cast

Jon Seltzer
Narrator (voice)

Jonathan Allen
Self (archive footage)

David Axelrod
Self (archive footage)

Rona Barrett
Self (archive footage)

Kate Bohner
Self

Tom Brokaw
Self (archive footage)

Pat Buchanan
Self (archive footage)

George W. Bush
Self

Jeb Bush
Self (archive footage)

Michael Caputo
Self

Ben Carson
Self (archive footage)

Katie Couric
Self (archive footage)

Alfonse D'amato
Self

Michael D'Antonio
Self

Donny Deutsch
Self

Bo Dietl
Self

Phil Donahue
Self (archive footage)

Doug Flutie
Self (archive footage)

Robin Givens
Self (archive footage)

Mark Halperin
Self

John Harwood
Self (archive footage)

Nikki Haskell
Self

Chris Hayes
Self (archive footage)

John Heilemann
Self

Caroline Heldman
Self (archive footage)

Michael Jordan
Self (archive footage)

Megyn Kelly
Self (archive footage)

Don King
Self (archive footage)

Ed Koch
Self (archive footage)

Reuben Kramer
Self

Matt Lauer
Self (archive footage)

Robin Leach
Self

David Letterman
Self (archive footage)

Robi Ludwig
Self

Omarosa Manigault
Self

Marla Maples
Self (archive footage)

Timothy L. O'Brien
Self

Barack Obama
Self (archive footage)

Clarence Page
Self (archive footage)

Rand Paul
Self (archive footage)

Jane Pauley
Self (archive footage)

Norman Vincent Peale
Self (archive footage)

Ross Perot
Self (archive footage)

Rick Perry
Self (archive footage)

Dan Quayle
Self (archive footage)

Danielle Pletka
Self (archive footage)

Nancy Reagan
Self (archive footage)

Ronald Reagan
Self (archive footage)

Mitt Romney
Self (archive footage)

Stephanie Ruhle
Self

Tim Russert
Self (archive footage)

Jon Seltzer
Self

Gabriel Sherman
Self

Robert Shrum
Self (archive footage)

Michael Spinks
Self (archive footage)

Linda Stasi
Self

Charley Steiner
Self

Roger Stone
Self

Chuck Todd
Self (archive footage)

Donald Trump Jr.
Self

Donald Trump
Self

Eric Trump
Self (archive footage)

Ivana Trump
Self (archive footage)

Ivanka Trump
Self (archive footage)

Melania Trump
Self (archive footage)

Tiffany Trump
Self (archive footage)

Mike Tyson
Self

Jesse Ventura
Self (archive footage)

Herschel Walker
Self (archive footage)

Chris Wallace
Self (archive footage)

Rick Wilson
Self (archive footage)

Liz Smith
Self

Jim Whelan
Self

Kurt Andersen
Self