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20 Rare Photos of Donald Trump You've Probably Never Seen Before

Baby Trump

Who would’ve thought Donald Trump was such a cute kid? This 1946 photo of Trump shows an adorable blondie with big blue eyes that could charm just about anybody.

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Trump and Siblings

This probably early-1950s photo shows Donald Trump (left) with the rest of his siblings, Fred Jr., Robert, Maryanne, and Elizabeth.

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Trump’s Military School Days

Donald Trump’s 1964 senior portrait for the New York Military Academy. After he graduated from the NYMA, Trump went on to graduate from the University of Pennsylvania’s Wharton School of Finance and Commerce.

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Ladies’ Man Trump?

While he was attending the New York Military Academy, Trump was voted by the student body as a “Ladies Man” for the 1964 edition of the yearbook.

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Sports Fan at Heart

Hailed as Golf Digest’s best-golfing president, it shouldn’t come as a surprise that Donald Trump is an avid sports fan. During his younger years, Trump was also active in playing football and baseball while he attended the New York Military Academy.

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Donald and Ivana, Round One

Married on April 7, 1977, at the Marble Collegiate Church in New York, Ivana was Donald Trump’s first wife. The two had three children together, Donald Jr., Ivanka, and Eric, before the pair split in 1991.

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Picture-Perfect Family

In 1986, the Trump family posed for a family photo, looking every part of the picture-perfect family of the time. The photo included Trump’s first wife, Ivana, and their three children.

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Donald and Marla

After a very public affair and messy divorce from his first wife, Donald Trump and Marla Maples married on December 20, 1993, at New York City’s Plaza Hotel. The marriage came just two years after Trump divorced from Ivana and two months after the birth of Donald and Marla’s daughter, Tiffany Trump.

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Doting Dad

Seen here with his eldest son, Donald Jr., Trump looks like the typical American dad. Y’know, if American dads had millions of dollars to spare.

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Young Trump With His Kids

Posing with his kids for a family photo, Trump looks incredibly proud of his three beautiful little blondies. 

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Trump Meets Rocky

At a 1997 charity event for Lupus, Trump is shown getting chummy with Rocky star Sylvester Stallone. Stallone and Trump have stayed in contact over the years. When Trump became president-elect, there were rumors that he’d pick Stallone for the role of Chairman of the National Endowment for the Arts.

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Daddy’s Girl

Donald Trump and his eldest daughter Ivanka peek over the crowd of a tennis match during the 1994 U.S. Open in New York. Over the years, Ivanka has proved herself a valuable asset to the Trump brand and currently acts as an influential political adviser to her father in the White House.

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Walking With Giants

Trump’s always been a sports fan, so it’s honestly not too surprising that he was into wrestling. In 1988, Wrestlemania IV was hosted at Trump Plaza in Atlantic City, NJ, which led to this photo of him holding the championship belt between wrestling legends Hulk Hogan and Andre the Giant.

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Trump’s Friendship With O.J. Simpson

Surprisingly, O.J. Simpson was one of Trump’s closest friends and supporters. Trump stood beside Simpson, even throughout his various legal and personal battles.

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Third Time’s the Charm

On January 22, 2005, Trump married his current wife, Melania, at the Episcopal Church of Bethesda by-the-Sea in Palm Beach. The event attracted media attention and had several A-list celebrities attend. The two later had their son, Barron.

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Trump and Steven Spielberg

Although he's now an avid Trump-opposer, Donald Trump and Steven Spielberg were once on at least decent terms.

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Trump Meets the King of Pop

In April 1990, Michael Jackson and Donald Trump were photographed on a plane, awaiting takeoff to visit child AIDS patient Ryan White. Supposedly, Jackson lived in Trump Tower for a time and would even babysit his three oldest children.

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Trump With the Reagans

Back in August of 1983, the Reagan’s greeted Donald Trump during a reception for Eureka College Scholarship recipients in the White House’s State Dining Room.

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Trump’s Real Estate Prowess

On March 2, 1976, Donald Trump met with Alfred Eisenpries, the NYC Economic Development Administrator, to show him the sketch of a new 1,400 room renovation project of the Commodore Hotel.

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Two Presidents Meet

After being named the president-elect, President Barack Obama invited Donald Trump to the White House for a meeting on November 10, 2016. The two met for the first time in the White House’s Oval Office, where they shook hands in front of the press.

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