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. The background hints at a cozy, well-to-do household, reflecting the prosperous upbringing of the future president.
This image captures a time of innocence and potential, long before the world would come to know his larger-than-life persona. It humanizes Trump in a way that many of his more public images do not, offering a softer, more personal side to the man known for his brash character.
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. In this striking photo, a young Donald Trump stands proudly in his old uniform.
With a disciplined posture and a confident gaze, the image reveals a glimpse of the strong-willed leader he would become. His neatly pressed uniform and polished demeanor suggest a serious and focused cadet committed to the rigors of military training. This photo underscores the early development of traits such as leadership, resilience, and a sense of duty, which have been pivotal throughout his career.
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. Captured during his prime, this photo showcases Donald Trump next to a beautiful woman. Dressed in a relaxed outfit and trademark hairstyle, he looks a bit shy.
This image hints at his magnetic personality and the allure he held for many despite looking a bit more reserved. It reflects a period in his life where his charisma was blooming and is a snapshot of a man who was always at the center of attention and thrived in the company of others.
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.
Dressed in a complete NY Yankees baseball uniform, he poses with his kids on the field. This image highlights his genuine interest in sports and persona as a "family man." It’s a reminder that behind the millionaire mogul, there is a man who finds joy in America's favorite pastime, just like millions of others.
Picture-Perfect Family
In 1998, 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 two children.
The backdrop, likely their luxurious home or at a lavish event, underscores their wealthy lifestyle. Novice young Ivanka and her brother, both dressed impeccably, and her mother, Ivana, complete the picture of a cohesive family unit, which is ironic, considering the oncoming divorce.
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.
Trump has always fostered a connection to popular culture and mingled with Hollywood stars on red carpets and on film sets. It showcases a lighter, more approachable side of Trump, who clearly enjoys the company of celebrated figures as well as being the center of attention.
Daddy’s Girl
Donald Trump and his eldest daughter Ivanka are caught in a candid photo. 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.
This image highlights the supposedly strong bond between Trump and Ivanka. For those who value family connections, this photo is a strategic way to make Trump look like a loving family man.
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 him meeting wrestling legends Hulk Hogan and Andre the Giant.
Dressed in a sharp suit, Trump exudes confidence and authority, fitting right in with the powerful company he keeps. Nobody can deny his ability to navigate circles of power even long before his presidency. This drive propelled him to the forefront of American business and, eventually, politics.
Trump and Steven Spielberg
This intriguing photo features Donald Trump with legendary filmmaker Steven Spielberg. Both men are dressed in suits, but aren't engaged in conversatio In fact, their blank faces suggest they're from two very different worlds. Although Spielberg is now an avid Trump-opposer, they were once on at least friendly terms.
The setting, likely a high-profile event or gala, underscores their status as influential figures in their respective fields. Trump loves worming his way into Hollywood circles, which solidifies his image as part of pop culture.
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.
But here's another picture of them together that you probably haven't seen before. Michael Jackson flashes his signature smile with an awkward thumbs up while Trump evidently tries to get his attention.
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. Of course, he's dressed in a sharp suit and stands offsides, anticipating a conversation with the Presidential pair.
The setting is packed with affluent people, which adds to the moment's significance as it emphasizes the huge network of relationships he's nurtured. Trump's early connections to influential political figures, showcasing his presence in elite circles that have helped prop up his political career.
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.
If you don't know the context for this image, it looks like he's giving a tour of his home for Architectural Digest or MTV Cribs. We can't lie; it's pretty cool to see such luxurious mansions, and his involvement with real estate extends to everything including his notorious Trump Towers.
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.
Ironically, this image underscores Trump’s longstanding connections with key political figures and his presence in influential circles. It's a solemn reminder of Trump’s early involvement in political and social affairs before he turned on Obama and his allies. His strategic networking skills served him well in the long term, which is largely how he gained the presidency in the first place.
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.
Tiffany is missing in this photo, but Ivanka stands close by. The trio pose together, likely at a high-profile event or in one of his many luxurious properties. Many want to prop him up as a family man, but he seems better at starting families than sticking with them.
Trump With Doug Flutie at a Press Conference in Trump Tower
In this dynamic photo, Donald Trump is seen alongside football star Doug Flutie at a press conference in Trump Tower, which emphasizes Trump’s involvement in the world of sports and his ability to draw high-profile athletes to his ventures.
This photo highlights Trump’s knack for creating buzz and excitement around his projects, showcasing his promotional skills and his ability to connect with influential personalities.
Trump Shaking Hands With Then-President Bill Clinton
This striking photo features Donald Trump shaking hands with then-President Bill Clinton. Both men are dressed in formal attire, with Trump’s confident smile and Clinton’s friendly demeanor highlighting the mutual respect between them. The setting, likely a high-profile event or gala, adds to the significance of the encounter.
For his supporters, this photo serves as a reminder of Trump’s longstanding engagement with key political figures, showcasing his networking skills and the respect he garnered from leaders of different affiliations. It reflects his strategic approach to building connections and his influence in political and social arenas long before his own presidential run.
Donald Trump With Jesse Jackson at the Mike Tyson vs. Michael Spinks Boxing Match
Here, Donald Trump is seen with Jesse Jackson at the Mike Tyson vs. Michael Spinks boxing match. Both men are dressed in suits, with Trump’s enthusiastic expression and Jackson’s attentive demeanor capturing the excitement of the event.
The background, which is filled to the brim with attendees, underscores Trump’s ability to bridge different worlds, from business to sports to civil rights, showcasing a multifaceted character who thrives in various environments.
Trump Dining With Jesse Jackson
In this candid photo, Donald Trump is seen dining with Jesse Jackson, engaging in what appears to be a lively conversation. Both men are dressed in suits, with Trump’s animated expression and Jackson’s attentive listening capturing the moment. The setting, likely a high-end restaurant, underscores the importance of their meeting
Unlike today, this image highlights Trump’s willingness to engage with diverse figures. Even so, it reflects his strategic approach to relationship-building and his presence in significant social circles. In the end, those relationships benefit him more than they do the other person.
Trump Holding Up a Picture With the Prince of Pop
Donald Trump holds up the infamous picture of him with Michael Jackson on a plane. Both men are smiling, and the fact that people bring these photos to his political rallies means his Hollywood networking paid off.
For those who support Trump running for political office, this photo is a reminder of his ability to build relationships with celebrated (and largely controversial) figures. His charisma drew many people to him over the years, but only a few actually stuck around.
Ivanka Finds a Place to Sit
In this tender photo, a young Ivanka Trump sits on her father’s lap, looking up at him with adoration. Donald Trump, dressed in a casual suit, looks past her at the entertainment beyond. This image is used to prove that he's a supportive father.
It reflects his nurturing side and the pride he takes in his family, offering a glimpse into the personal life of a man often seen through the lens of his public persona. And for the next president, people are looking for someone genuine and relatable. For many, he ticks those boxes.