23 Incredible Pictures of Young Donald Trump

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It’s almost hard to imagine Donald Trump as a kid given his cutthroat attitude running multiple businesses for so many years, but young Donald Trump was actually a very adorable boy (and eventually very handsome teenager.) This list showcases 23 amazing pictures of Donald Trump as a young man, including photos of him as a child, his years in military school, college photos, and much more.

Plenty of information is included with these photos of Donald Trump through the years, so expect to learn a lot about his beginnings and where he went to school. You’ll also learn about Donald’s siblings, parents, businesses, and a lot more. He has certainly had a very interesting life, and although he was born into privilege, he is still one of the hardest working men on the planet who always put 100% into anything that he did.

1. Donald Trump As a Kid

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Donald Trump was born in Queens on June 14th, 1946. Between him and his four other siblings, he was the second youngest. The photo above was posted to Trump’s official Instagram page with the caption, “Who knew this innocent kid would grow into a monster?” Don’t be so hard on yourself, Mr. President!

2. Young Donald Trump With All His Siblings

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Young Donald Trump is pictured with all his siblings in this photo, taken some time in the ’50s. From left to right: Donald, Fred Jr, Robert, Maryanne, and Elizabeth. All of Trump’s siblings are alive today except Fred Jr, who unfortunately died from alcoholism in 1981. Donald cites his older brother’s death as the reason he doesn’t drink or smoke cigarettes.

3. Donald Trump’s Confirmation Photo

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President Trump was only 13 years old in this photo, taken at the First Presbyterian Church in Jamaica, Queens, in 1959. Given his German ancestry, Trump’s family were originally Lutherans, but eventually joined the Reformed Church in America.

4. Young Trump and Siblings a Little Older

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Another family portrait of Donald Trump with his brother’s and sisters. Everyone looks a little more grown up! Taken some time in the mid to late ’50s.

5. Young Donald During His Military Academy Years

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Here’s a very handsome young Donald Trump at age 18 posing for his yearbook photo at the New York Military Academy. Trump enrolled at NYMA when he was 13 years old, where he finished 8th grade and all of high school. He attained the rank of captain during his senior year.

6. Donald Trump With the NYMA Baseball Team

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Donald Trump played a few different sports in high school, including baseball. Here he is pictured with the varsity baseball team, holding the ball with one of this teammates.

7. Donald Trump Played Soccer When He Was Younger Too

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Who said Donald was athletic when he was younger? Taken in 1964 during his senior year, here is another photo of Young Trump from the NYMA yearbook, pictured with the soccer team. He didn’t get to hold the ball this time!

8. Young Donald Trump in a Basketball Picture

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Is there any sport this man didn’t play in high school? Pictured above is Trump along with some teammates from the intramural basketball team.

9. Another Yearbook Photo of “Ladies Man” Donald Trump

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Apparently Donald Trump was the quite the ladies man in his younger years. This yearbook photo and caption describe him as such. This photo was taken from the “popularity poll” page of the 1964 NYMA yearbook.

10. Trump Doing Marching Drills at NYMA

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This is a man who knows how to march in step. Pictured second from the left, Donald Trump is seen here doing a marching drill with some of his fellow cadets.

11. Trump in Military Academy With His Proud Parents

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Posted on Trump’s Instagram page, here he is pictured with his proud parents Fred and Mary Anne. Trump graduated from the NYMA in 1964, and began college the same year.

12. Donald Trump’s College Graduation Photo

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Although Donald Trump attended Forham University in the Bronx starting in August 1964, he transferred to the Wharton School of the University of Pennsylvania two years later to study real estate. He graduated in 1968, where he is pictured above with his father Fred.

13. Trump and his Siblings All Grown Up

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The third sibling photo on this list, here are the Trump brothers and sisters all grown up. Pictured from left to right are Robert, Elizabeth, Fred Jr, Donald, and Maryanne.

14. Donald Trump in his Late 20s Pictured With His Dad

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Taken in 1975, this photo shows Trump and his father Fred on Father’s Day, two days before Donald’s 29th birthday. The caption on his Instagram page where he posted it reads, “#TBT With my father, Fred Trump, in Brooklyn,1975. A great Father’s Day gift a stay at my 5 star hotel along with items from my signature collection.”

15. Donald Trump Pictured With His Cadillac

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Taken a year later in 1976, here is Young Donald Trump pictured with his Cadillac (and custom vanity plate.) Taken for a New York Times article, the original caption read, “Donald Trump getting into his Cadillac to begin a day of real estate deals.”

16. Trump in the 1970s With His First Big Project

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Pictured again in 1976, one of Donald Trump’s first major projects was the purchase and renovation of the Commodore Hotel outside of Grand Central Terminal. He was only 30 years old at the time.

17. Trump Holding His Newborn Son in 1978

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Donald Trump Jr. was born in 1977, and is the eldest of Donald’s children. Here is a young Donald Trump as a proud father, holding his son.

18. Donald Trump on the Oprah Winfrey Show

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Flash forward 16 years later where Donald Trump appeared on the Oprah Winfrey show, teasing a run for President of the United States. You can watch the video the clip was taken from here.

19. Younger Donald Trump With Don King and Jesse Jackson

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Age 42 now, here is Donald pictured with Don King, Jesse Jackson, and John H. Johnson.

20. 40 Year Old Trump Meeting to Stop Illegal Peddling

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Taken in 1986, Trump has always championed again illegal activity, whether it be immigration or drug peddling on the streets of New York.

21. Donald With His Late Father Fred

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Unfortunately Fred Trump passed away in 1999, but he would have undoubtedly been so proud of his son’s accomplishment of getting in the Oval Office.

22. Donald Trump and his Three Beautiful Children

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Taken in 1993 with his beautiful children, this photo shows that Trump has always been an excellent father who knew how to instill values into his children.

23. Hilarious Video From The Mayor Giuliani’s Press Roast

We have to end it with this hilarious video of Trump smooching Mayor Giuliani in drag. The video was a skit for the Mayor’s Inner Circle Press Roast from 2000. Apparently Trump thought the mayor was beautiful as a woman, and asked what kind of perfume “she” was wearing.
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