This photo attests to how dapper and serious Donald Trump was when inking a business deal. An expert in the real estate industry, Trump knew how to work his way up to success and seal a deal with his elite clients.
We hope his skills in sales and people management will also turn out just fine in politics.
Trump Meets The Incredible Hulk
A regular patron in the theatrical world of professional wrestling, seeing Trump with WWE superstars is a common scenario. This candid photo of the Trumpster and retired pro wrestler, Hulk Hogan, is an affirmation of their alliance.
The legendary wrestler is such a strong supporter of Trump that he was one of the many celebrities who reacted publically and positively to Donald Trump’s victory in the 2016 presidential race. “Thank you God for the highly favored miracle, thank you for the shift and thank you for the truth,” Hogan tweeted.
Vacation Donald
Wow! We are so impressed with the young T-Dog in this snap as he looks so cool and chic in his stylish retro-inspired outfit. We’re guessing this photo was taken sometime during the ‘80s. He appears ready to rock and roll into any party that happens to be in the vicinity.
Being the celebrity that he is, Trump must have mastered the art of power dressing.
Trump, The Romantic
It is not a secret to the public that Trump’s romantic side led him into three marriages. After his failed marriage with the Czech model, Ivana Zelníčková, Donald found love with actress, Marla Maples.
The ex-couple looks every bit of "young and in love" in this photo. Sadly, their marriage fell apart after seven years. They have a daughter named Tiffany who was raised by Maples in California.
Trump And Rocky
A younger Trump was photographed with one of Hollywood’s biggest superstars: Sylvester Stallone. Looking every inch ecstatic, the future president was totally nailing his fan mode with the famous Rocky Balboa.
We cannot deny the fact that Trump has made a lot of friends in the TV and film industry, thanks to his cameos and of course, popularity. The two celebrities met at one of Donald’s casinos in Atlantic City for a promotional boxing match.
Happy Family
We barely see Donald Trump flash his genuine smile nowadays. Perhaps because of the pressures of his role as the president of the United States. Nevertheless, his younger years proved he is in possession of a softer side, one brought out by his kids and then wife Ivana.
Family photo for the win – one look at their happy faces and you can tell love is in the air behind this snap.
Daddy’s Little Girl
We couldn’t agree more that Ivanka is her daddy’s princess. The eldest daughter, now her father’s senior advisor, is known to have a close relationship with Donald Trump. The daddy-daughter tandem was unbreakable, right from the start.
Well, nobody can argue on the fact that their love for each other survived many controversies, not the least of which being Donald’s election as America’s president.
Trump’s Friendship With O.J. Simpson
One of Trump’s closest friends/supporters is Orenthal James Simpson, a.k.a The Juice. Despite the many legal and personal battles of the former running back for the Buffalo Bills, and the San Francisco 49ers, Donald stood by O.J. and supported him in his lowest of lows and highest of highs.
Such an alliance is one for the books, and we’re in awe because really, true friends are hard to find.
Trump The Ladies Man
For almost two decades (1996 to 2015), Donald Trump owned part of the Miss Universe pageants like Miss USA and Miss Teen USA. As such, it’s only normal that he has created countless friendships with ladies.
Here’s the proof: a black and white photo with the pageant’s contestants, taken sometime in 1986.
The Man In The Uniform
While Trump was exempted from serving in the United States military due to medical reasons, this photo shows him posing in a uniform when he attended the New York Military School.
What do you think about young Donald in his military uniform?
Trump Hits The Slopes
Looking young and happy, Donald Trump enjoys every bit of his ski trip. Both him and Ivana are reportedly big fans of ski vacations, loving both the cold weather and the thrills of skiing.
With his White House commitments, we’re wondering if Trump still has the luxury of time to invest in this exciting hobby?
Donald With The Heavy Weight Champ
Another close pal of Mr. Trump is “the baddest man on the planet,” Mike Tyson. Despite the many nicknames Tyson has accrued for his antics over the years, he remains an icon in the boxing industry and, of course, Trump wouldn’t let an opportunity pass without having a souvenir photo with his equally popular friend.
The photographer must have been thrilled with this... let’s say, “candid” photo that now makes rounds on the internet… for obvious reasons.
Business Is Business
With hotels, golf courses and casinos under his name, there’s no doubt that Trump is an expert in various businesses. So when he taped for a TV interview about his unprecedented success in the field, he was every bit the tycoon.
With mixed facial expressions, mostly serious, he waxed lyrical about the attitude necessary to be as big of a success as he was.
Donald And Ivana’s Wedding
This photo is evidence of a happy marriage. Taken in 1985, the couple are seen being greeted by Donald’s father. Fred Trump appears very happy and proud of his son’s greatest accomplishment at the time: marrying the woman of his dreams.
Unfortunately, the couple’s marriage fell apart after 15 years of union.
The Business Tycoon And The King Of Pop
We’ve been flooding you guys with photos of Trump with famous celebrities... and we don’t think we’re going to be able to stop anytime soon.
That said, here’s a cool picture of Donald and the iconic Michael Jackson. The president must be very lucky to have exchanged chit-chats with the King of Pop before he passed away.
Young Trump
This must be one of Trump’s finest photos, looking fresh, happy and proud during his days at the New York Military School.
While his outer shell may have changed, we hope this youthful vibe remains in him as he carries the biggest task on his shoulders: being one of the world’s most powerful leaders. How’s that dashing smile?
Proud Father
Being a first-time parent, Donald Trump looks proud and ecstatic holding his newborn son, Donald Trump Jr. This priceless memory is proof that even tough old Trump could be tender and loving when it comes to his children.
Fast-forward to the present day and Donald Sr. must be so proud that his son is following his footsteps in business and politics.
Baby Face
This rare photo of baby Donald Trump screams cuteness. How could it be that such an innocent face is now leading the United States, making headlines and history with his every statement and decision he declares.
Dear Baby President, we wish for peace, equality, and love to prevail in this country. Are you with us?
Trump And Maples
This classic photo of young lovers, Donald and Marla, was taken at his golf course in Mar-A-Lago. Like the actress that she is, Marla exudes elegant drama in this luxury room fit for a chic couple like them.
Marla Maples was Trump’s second wife. They divorced after six years of being married and have a daughter named Tiffany.
Papa Trumps
When it comes to the Trump family, it seems business runs in the blood. Fred Trump, Donald Trump’s father, was a real estate developer in New York City. Prior to his death, he appointed Donald as the president of the Trump Management Company. The rest, as they say, is history.
Fred knew that Donald would make things bigger. True to his father’s faith in him. Donald expanded the family’s business ventures to the value of billions of dollars. Not to mention the fact that he’s taking a turn as the 45th president of the United States.
Trump Vs. The Media
As they say, good or bad publicity is still publicity. As such, the media doesn’t mind whether Trump’s statements are misleading or his views are racial, the press is just after high-ratings.
Now that he’s giving America a daily, steaming-hot serve of presidential remarks, every word uttered and every move made by Donald is scrutinized by the press.
Trump’s Expertise In Real Estate
This photo attests to how dapper and serious Donald Trump was when inking a business deal. An expert in the real estate industry, Trump knew how to work his way up to success and seal a deal with his elite clients.
We hope his skills in sales and people management will also turn out just fine in politics.
Trump Likes The Ladies
Having had the opportunity to co-own Miss Universe pageants, Donald Trump made sure he was able to get up close and personal with the lovely women competing. In this photo, he stole a kiss on the cheek as his means of congratulating this beauty pageant winner.
We’re confused about whether the lovely lady was surprised with the overly sweet gesture or just amazed at Trump’s presence.
Trump’s Family Portrait
Can you spot Donald Trump in this photo? The young boy standing on the far left exudes class and elegance in a suit matched with his simple smile and upright posture.
This classic family photo shows a young Donald with his siblings; older sister Maryanne (sitting on the right), brother Fred Jr. (sitting at the left of Maryanne), younger sister Elizabeth (standing in the back) and little brother Robert (standing at the far right of the picture). Don’t they make a beautiful family?
Not Camera Shy
Long before being elected to office as the current president of the United States, Donald Trump was already making waves thanks to his grand business ventures and TV appearances.
This photo was taken in one of his countless TV interviews and, by looking at it, Trump appears casually cool and comfortable. We guess that’s the power of confidence and communication skills.
Trump And Barbara Walters
This photo depicts what seemed to be a casual friendship between Donald Trump and the late veteran journalist Barbara Walters. Donald looks happy and carefree, feeding (an equally cheerful) Barbara a snack. Their friendship, though, was one of the greatest examples of why we’re encouraged not to talk politics with those we love.
When Trump served as a Republican president, the two were diametrically opposed. Did that mean the former pals were enemies? Possibly, judging by that infamous interview in which Walters challenged Trump on a number of key issues.
Trump On Canvas
Trump looks positively holy here with the sky and rays of Godly light as a backdrop. The artist of this painting must be a big Trump supporter given the soft and transcendent image he created of this endlessly controversial figure.
In this impressive painting, Donald Trump almost looks supreme with that heavenly background behind him.
Teenage Donald
Even during his teenage years, Donald bore the charm of a handsome guy who could easily make women fall for him. This old photo of a young Trump with a lovely woman is proof that he’s a lady-magnet (thankfully it appears she has his hand well under control).
Who could forget his countless photos with beauty pageant contestants and winners as he congratulated a few of them with a stolen kiss? Then, of course, all the beautiful women he had relationships over the years.
Trump’s USFL Days
One of Trump’s side ventures in the past was sports, specifically the New Jersey Generals football team, which he purchased in September 1983.
Trump’s team played in the United States Football League (USFL). However, the league folded due to conflicts of interests between Trump and his business partners.
Trump And Walker
Being the owner of the New Jersey Generals of the United States Football League (USFL), Trump was fortunate enough to have the world’s greatest running back, Herschel Walker.
However, after his two-year career in the league, Walker moved to the National Football League (NFL) and played for the Dallas Cowboys. Well, some good things never last.
Special Bond
Being the eldest daughter, Ivanka remains a favorite of her dad. Since her younger days and until now, her closeness with her father is undeniable.
Pictured here is a young Ivanka, escorted by her dad to a black tie event.
The Little Trumps
From the proud look on Donald Trump’s face here, you can see he has a great love for his children. Photographed with his lovely kids in formal attire, this Trump family portrait is a picture of bliss and pride.
Who wouldn’t be proud when you have beautiful kids like Ivanka, Donald Jr., and Eric?
The Dapper Trump
Always in suit and tie, Donald Trump looks dapper, day in and day out. This photo does not reflect the pressures and challenges he faced with his various business failures over the years.
Rather, it reflects his perseverance and ability to always get inspired and rise up again. If you’re not convinced, you have to admit, his present role on the world’s stage is a testament to how powerful he is.
Cool As A Cucumber
To say that Donald never loses his temper is a big joke. This picture shows how relaxed the future president was but present reality suggests that he rarely keeps his cool. Think of the endless verbal bashing he gets from people around the world.
With social media as powerful as ever, Trump cannot escape the constant criticisms. He’s used to the negativity but that doesn’t stop him lashing back in hilarious Trump style.
Trump Among Legends
(Left to Right) Boxing promoter Don King, Donald Trump, entrepreneur Malcolm Forbes, and civil rights activist Jesse Jackson. These guys clearly had the time of their lives enjoying each other’s company.
We’re sure they were catching up while chatting about business, sports, and of course, politics.
Trump On The Big Screen
Trump is the living embodiment of versatility, skilled in business, sports and, would you believe it, acting. With many appearances on the small and big screens, Trump’s characters, no matter the exposure, are significant.
While many pan his performances as laughable, he wouldn’t be invited to any castings if his presence didn’t stir a reaction.
Of Giants And Men
A huge supporter of wrestling and its biggest stars, Trump snags photo ops with them on as many occasions as he can manage. In this photo, the business magnate poses with legendary wrestlers, Hulk Hogan, and Andre the Giant at a Wrestlemania event in Trump Plaza held during March of 1988.
Looks like Donald is not bothered by the tension between the two wrestlers at his back.
Cool Dad
Despite young Donald Trump Jr.’s reluctance to have a photo, his dad wasn’t bothered at all. Donald Sr. clearly understood the mood swings kids go through and was fine with young Donny not craving the limelight.
Now that he’s mature enough, Donald Jr. has become as used to the constant snaps from the press as his camera-loving dad. If you have a father as president, you pretty much have to resign yourself to a life lived in the public eye.
Why So Serious?
Donald Trump has many faces, from cool to serious. The one rarest to capture? Serious Trump in a light mood. With so many controversies chasing him since his run as a Republican candidate (even more now that he’s a president), his current face of choice is far from this relaxed demeanor of old.
Trump’s new style is tough and strict, often mid-yell with a pointed finger slicing the air above him.
Trump Partying With Celebs
Seen in this photo are real estate developer, Donald Trump and his wife, Ivana. The couple is flanked by Michael Douglas and then wife, Diandra Luker.
Michael and Diandra supported Donald in celebration of his book, The Art of the Deal, at Trump Tower. We didn’t know Donald was also a successful author.
Donald And Ivana
Donald’s first wife, Ivana, is seen enjoying the party in this photo. Accompanied by her then-husband, the former model must be proud of her ex-partner’s accomplishments especially now that he’s trying to make America great again.
In fact, Donald hosted Ivana’s wedding to Rossano Rubicondi in April 2008 at his Mar-a-Lago estate. Proof that ex-lovers can be great friends, too.
Luxury Cars
With billions of dollars in his bank account, it’s no surprise that Donald Trump has a collection of vintage and luxury cars. In this photo, he is sitting comfortably in this 1988 Cadillac Limousine.
We can just imagine his huge and extravagant car collection, equipped with the most advanced security and safety features.
Happy Days
When Donald and Ivana were still a couple, their photos were a revelation of their happy memories. One of the many parties they attended together was the yearly dinner dance of the Costume Institute at the Metropolitan Museum of Art in New York City.
Looking fab and happy, the couple was picture ready for the night.
Donald And Muhammad Ali
Meaningful moments in sports are not missed by Trump, as evidenced by this photo with the biggest legend of boxing, Muhammad Ali.
Young Donald was shaking hands with Muhammad, joined by Governor Thomas Kean, in Atlantic City. Trump knew well how to win over powerful affiliates.
With The Round Girls
If you think Donald is only fond of having pictures with boxing and wrestling legends, you’re absolutely wrong! In a Tyson vs Spinks fight in Atlantic City, the avid fan of boxing and its stars took time to pose for a photo with the round girls.
It’s hard to say who requested the snap (The Don is, after all, a self-confessed fan of beautiful women), but if we base it on the picture, these ladies were certainly bearing the biggest smiles.
Donald and Oprah
One of Trump’s most famous pals is the “Queen of All Media,” Oprah Winfrey. The successful businessman had a meaningful friendship with Oprah, as evidenced by the cozy way she’s cuddling up to him in this picture. The pair considered themselves buds... until Trump ran for office, that is.
Oprah was not impressed and Trump called her out via his Twitter account for being “insecure.” This was seven years after he tweeted that he was excited to be a guest on her show. If we’ve learned anything from this walk down Trump’s memory lane it’s this: friendships and politics don’t mix.
Trump And The King Of Pop
It’s clear that the prince of real estate can’t get enough of the King of Pop. This photo was taken in April 1990, during the grand opening of Taj Mahal casino, originally known as the Trump Taj Mahal.
As the owner, Donald made sure he allowed in only the finest guests to promote his business. The guy sure knows how to market his businesses, we’ll give him that.
Trump, Marla, and Evander Holyfield
Donald may love snagging snaps with his favorite celebrities, but he has a fair share of his own fans as well. In this photo, he is seen signing his book, The Art of Deal, for the professional boxer, Evander Holyfield. Holyfield looks happy receiving his personal copy of Trump’s signed book.
Also, actress Marla Maples is spotted here, waiting in the background to watch the Tyson vs. Williams fight with Trump in Atlantic City. During this time, Trump and Maples were rumored to be having an affair. This was before Trump had finalized his divorce with Ivana.
Trump Doing Blue Steel Before It Was Cool
You’ve witnessed several photos of Donald Trump in his youth that revealed his softer side, from his cute baby photos to his doting parent role with his children. But we cannot ignore the fact that Trump was rocking the blue steel look well before Zoolander made it a thing.
Think of the countless times he’s made false statements. Now imagine him doing it with this look on his face. Suddenly believable, right?
Best Friends Forever
As a public figure, even prior to his position in the White House, Trump was already famous thanks to his successful business ventures and TV appearances. His notoriety was only bolstered by his frequent appearances at major sports events, like his all-time favorite: the WWE.
Here he is seen taking yet another photo op with an impressively huge champion wrestler, Hulk Hogan. The two are known to have been pals for a long time and Hogan was one friend who remained a staunch supporter of Trump after he was elected president.
Donald’s Support Of Boxing Legend
Aside from Hulk Hogan, Mike Tyson also received a huge amount of support from businessman, Donald Trump. Seen in this photo (L-R) is promoter Don King, Trump, Tyson, boxer Michael Spinks, and his manager, Butch Lewis.
The snap was taken during Tyson and Spinks’ publicity event at Taj Mahal Hotel, which Trump owned at the time.
Donald And Jack Johnson
Trump’s softer side is also shown in his compassion to others who were unfairly treated. Prior to issuing a pardon to the late boxer, Jack Johnson, the two used to be pals and would attend special occasions together.
Johnson was the first African-American world heavyweight boxing champion who was jailed for his relationship with a white woman.
Mr. And Mrs. Trump
Trump’s 15 years of marriage with former wife, Ivana, had a lot of blissful memories, including the births of their three children, Donald Jr., Ivanka, and Eric.
The Czech model was supportive of her husband, always accompanying him to events and dazzling the camera with her genuine smile. This photo was taken at Trump Plaza Casino Hotel in New Jersey.
Trump And Pacheco
Muhammad Ali’s trusted “fight doctor” Ferdie Pacheco was photographed in the thick of things with Donald Trump. Pacheco served as Ali’s ringside physician for a long time. When the heavyweight champ refused to follow Pacheco’s advice to retire from boxing to protect his health, Pacheco retired instead.
While the two weren’t in agreement, Pacheco made it clear he was proud of Ali for the unprecedented accomplishments he made in his boxing career.
Trump With His Actor Pals
Trump’s Castle Casino Hotel in Atlantic City is New Jersey’s home of special occasions and the brightest of stars.
This 1989 photo of Trump shows him seated on the same table as actor, Don Johnson, and actress, Melanie Griffith, who were a couple at the time. Johnson and Griffith are the parents of Dakota Johnson.
Young, Rich Trump
Following in his father’s footsteps as a real estate developer, Trump put hard work and dedication into their family business. With billions of dollars in sales, Trump became a business tycoon and was able to afford a luxurious lifestyle.
This photo of a young Trump was taken sometime in 1973 when he was still 27 years old. He was being featured for an interview and the accompanying photo was taken in his lavish 3-bedroom penthouse.
Trump And The Football Legend
Herschel Walker is one celebrity who, after Trump announced his candidacy, continued to support the man who had once supported him. Now, as America’s president, Trump still enjoys the backing of this football legend.
During Trump’s campaign period, Herschel was quoted as calling Donald his “front runner” for president. Walker used to work for Trump as a running back on his USFL team, the New Jersey Generals.
Trump The Sports Fan
Aside from owning numerous golf courses in America and other countries, Donald Trump is also a big fan of baseball and football. He was active in playing these sports in the New York Military Academy and was even scouted by the Red Sox and Phillies.
Who knew that the 45th President of the US was skilled in these athletic activities? To be hailed as the best-golfing president by Golf Digest, he must be really a pro.
Trump’s Second Wife
After his divorce with Ivana, Donald Trump married actress, Marla Maples. Their union lasted for six years and Maples ended up raising their daughter, Tiffany, in California.
This photo shows a young Tiffany carried by her mom during the launch party for Trump International Tower in London.
Third Time's A Charm
Six years following his divorce with Marla Maples, Trump married Slovenian model, Melania Knauss. Melania became the first lady when Trump was inducted as president in January 2017.
In this photo, Trump and a stunning Melania are sporting matching, enigmatic smiles at the Cipriani Dinner Concert Series. Donald and Melania have a son named Barron.
Fatherhood
First-time father, Donald Trump, was photographed with first-born son Donald Jr. in this sweet-as-a-pie picture. You can clearly see the bliss and pride in big Don’s face.
It is the epitome of a man smitten in the presence of his little angel. Donald Jr. now serves as an executive director of his father’s real estate empire.
Daddy Donald
There’s that robe again! But this time it’s wrapped around its owner in a whole different pose. Arguably, Trump’s best role was being a loving father to his children.
We won’t get tired of being flooded with photos of Daddy Donald with his kids, as it’s refreshing to see the side the media neglects. Despite his tough personality, his gentle side shines through when he’s with his beautiful children.
Tiny Ivanka And Daddy Trump
Considered a definite daddy’s girl, and the favorite child among her siblings, a young Ivanka is seen here wearing her birthday hat, carried by Donald during her birthday party.
Now officially known as the First Daughter of the United States, Ivanka is actively supporting her father’s political activities as his senior adviser.
Life Of The (Birthday) Party
Photographed at a tennis match, Donald Trump shows his sweet side as he sits next to little Eric while the cute kid was busy eating a hot dog. Hats off, Mr. President!
You’re doing a great job as an attentive and caring father to your children.
The Lovely Ivana
This photo was taken during the former couple’s happy days. It’s clear why Donald was smitten with Ivana. The former Czech model is a picture of elegance and beauty. Unfortunately, her marriage to Trump wasn’t meant to last forever.
The good thing is that they have three beautiful and successful children, Donald Jr., Ivanka, and Eric.
Donald’s Second Marriage
Donald Trump clearly believed that marriage is lovelier the second time around (and even sweeter on the third go?), hence his second wedding.
This photo illustrates love, pride, and happiness between the newlyweds, Donald and Marla. The former couple’s wedding took place at New York City’s Plaza Hotel on December 20, 1993.
Trump and Obama
After his controversial win as America’s 45th president, Donald Trump was invited by President Barack Obama to the White House for a meeting. The two leaders shook hands in front of the press in the Oval Office.
This was the first meeting of Trump and Obama and Donald’s very first visit to the White House. Did you notice Obama’s not-so-interested face while shaking hands with Trump? We cannot blame him.
Donald, Marla, and Tiffany
This portrait of Donald Trump with his second wife, Marla Maples, and their daughter, Tiffany, was taken in 1996 at the Mar-a-Lago estate, Palm Beach, Florida. Did you know that Tiffany was named after luxury jewelers, Tiffany & Co?
Here’s another Tiffany fact for you: Trump had to purchase the air rights of the Tiffany & Co store in New York City in order to be able to build the Trump Tower the way he wanted it.