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Summary

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.

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Cast

  • David Axelrod

    David Axelrod

    Self (archive footage)

  • Rona Barrett

    Rona Barrett

    Self (archive footage)

  • Tom Brokaw

    Tom Brokaw

    Self (archive footage)

  • Pat Buchanan

    Pat Buchanan

    Self (archive footage)

  • George W. Bush

    George W. Bush

    Self

  • Jeb Bush

    Jeb Bush

    Self (archive footage)

  • Ben Carson

    Ben Carson

    Self (archive footage)

  • Katie Couric

    Katie Couric

    Self (archive footage)

  • Bo Dietl

    Bo Dietl

    Self

  • Phil Donahue

    Phil Donahue

    Self (archive footage)

  • Robin Givens

    Robin Givens

    Self (archive footage)

  • Mark Halperin

    Mark Halperin

    Self

  • Nikki Haskell

    Nikki Haskell

    Self

  • Chris Hayes

    Chris Hayes

    Self (archive footage)

  • John Heilemann

    John Heilemann

    Self

  • Michael Jordan

    Michael Jordan

    Self (archive footage)

  • Megyn Kelly

    Megyn Kelly

    Self (archive footage)

  • Don King

    Don King

    Self (archive footage)

  • Ed Koch

    Ed Koch

    Self (archive footage)

  • Matt Lauer

    Matt Lauer

    Self (archive footage)

  • Robin Leach

    Robin Leach

    Self

  • David Letterman

    David Letterman

    Self (archive footage)

  • Robi Ludwig

    Robi Ludwig

    Self

  • Omarosa Manigault

    Omarosa Manigault

    Self

  • Marla Maples

    Marla Maples

    Self (archive footage)

  • Barack Obama

    Barack Obama

    Self (archive footage)

  • Rand Paul

    Rand Paul

    Self (archive footage)

  • Jane Pauley

    Jane Pauley

    Self (archive footage)

  • Ross Perot

    Ross Perot

    Self (archive footage)

  • Rick Perry

    Rick Perry

    Self (archive footage)

  • Dan Quayle

    Dan Quayle

    Self (archive footage)

  • Danielle Pletka

    Danielle Pletka

    Self (archive footage)

  • Nancy Reagan

    Nancy Reagan

    Self (archive footage)

  • Ronald Reagan

    Ronald Reagan

    Self (archive footage)

  • Mitt Romney

    Mitt Romney

    Self (archive footage)

  • Stephanie Ruhle

    Stephanie Ruhle

    Self

  • Michael Spinks

    Michael Spinks

    Self (archive footage)

  • Roger Stone

    Roger Stone

    Self

  • Donald Trump Jr.

    Donald Trump Jr.

    Self

  • Donald Trump

    Donald Trump

    Self

  • Eric Trump

    Eric Trump

    Self (archive footage)

  • Ivana Trump

    Ivana Trump

    Self (archive footage)

  • Ivanka Trump

    Ivanka Trump

    Self (archive footage)

  • Melania Trump

    Melania Trump

    Self (archive footage)

  • Tiffany Trump

    Tiffany Trump

    Self (archive footage)

  • Mike Tyson

    Mike Tyson

    Self

  • Jesse Ventura

    Jesse Ventura

    Self (archive footage)

  • Herschel Walker

    Herschel Walker

    Self (archive footage)

  • Chris Wallace

    Chris Wallace

    Self (archive footage)

  • Rick Wilson

    Rick Wilson

    Self (archive footage)

  • Liz Smith

    Liz Smith

    Self

  • Kurt Andersen

    Kurt Andersen

    Self