Donald Trump in His Youth

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Donald John Trump was born on June 14, 1946, to parents Fred Trump and Mary Anne MacLeod. The pair had married 10 years earlier. Donald Trump was the fourth of five children. He was born at the Jamaica Hospital Medical Center in Queens, New York. Trump’s family originated from Germany on his father’s side and Scotland on his mother’s side. Trump’s grandfather Frederick (originally Friedrich) first immigrated to the United States in 1885. He was just 16. He did not gain citizenship until 1892. It was shortly after this that grandpa Trump began to build the Trump family fortune. He was a savvy businessman and amassed the Trump family fortune by operating “boomtown” restaurants and boarding houses in the West.

Donald Trump shared the above “Throwback Thursday” photo of himself as a child on Facebook. However, the caption for the photo states, “Who knew this innocent kid would grow into a monster?” We’re assuming he was making a joke.

 

The Trump family gained a fortune thanks to Donald Trump’s grandfather, who operated “boomtown” restaurants and boarding houses in the Seattle area and Canada’s Klondike region during the gold rush. In 1902, Mr. Trump married Elisabeth Christ. In 1905, they resettled in New York, where they would stay the rest of their lives. That year, 1905, was also the year Donald Trump’s father, Fred, was born. Fred Trump went to work in the family real estate business when he was 15. In 1923, Fred Trump and his mother founded E. Trump & Son, which operated mostly in the Queens and Brooklyn boroughs of New York City. Fred Trump married Mary Anne MacLeod in 1936. They had five children together. From an early age, young Donald would prove to be one who followed his own rules.

Donald Trump shared the above picture of himself and his siblings to his Facebook page. Trump (far left) stands beside (from left) his older brother Fred Jr., his older sister Elizabeth Trump, his eldest sister Maryanne Trump, and his younger brother Robert Trump.

From kindergarten through seventh grade, Donald Trump attended the Kew-Forest School, a college preparatory school in Queens. At age 13, however, Trump was sent to the New York Military Academy, a private boarding school in Cornwall, New York. Trump was sent to the school as punishment because his parents had discovered he was making frequent trips into Manhattan without their permission. Trump would prove to be a popular student at the boarding school.

In this picture Donald Trump shared to his Facebook page, he says, “#TBT My confirmation picture at First Presbyterian Church in Jamaica, N.Y.”

 

While attending the New York Military Academy, Trump participated in numerous school functions, teams, and events. In this photo from the NYMA yearbook, Trump is brandished, the “Ladies’ Man,” next to an unidentified woman. It would take 50 years before the identity of the woman was discovered to be Fran Dunn, a secretary of the school, who was asked to appear in the photo to “crown” Trump with his new designation. Trump’s reputation as a “ladies’ man” would continue with him throughout the years through numerous scandals.

 

During his years of schooling at the New York Military Academy, Trump participated in numerous sports. He was, in actuality, a sturdy 6 foot, 2 inches tall. According to reports, he played football, tennis, squash, and took up golf. Photographs from the school also show him on the varsity baseball team (pictured). While most of these sports would fade away into watching hobbies for Trump, it was golf that would become a staple of his life decades later.

 

During his time at NYMA, Trump played on the football team (though he’s shown above with his soccer team); his love for the sport culminated in Trump owning his own football team in the future in his attempt to run a separate American football league to compete with the National Football League. We’ll discuss this failed venture in more detail later on.

 

 

Despite boasting of being “very military,” Trump received five draft deferments from serving in the military during Vietnam. Four of the deferments were for his time during college. The fifth was for a medical diagnosis of bone spurs in his heels, which has come under renewed scrutiny in recent years. According to the daughter of the podiatrist who diagnosed Donald, the bone spurs excuse was “favor” to Fred Trump in order for the podiatrist to maintain a close relationship with Fred, who was the podiatrist’s landlord.

 

If you have even a glancing understanding of Donald Trump, you know he does things his way. Trump shared this “Throwback Thursday” picture of himself in uniform at the NYMA. Trump had previously made the claim that being in the uniform made him “very military,” though he never served in the military. Decades later, Trump would find himself roiled in controversy after he criticized U.S. Senator John McCain for being captured and held as a prisoner of war during the Vietnam War. Trump dismissed McCain as a war hero, saying, “I like people that weren’t captured.”

 

Donald Trump graduated from the New York Military Academy in May 1964. That fall, he enrolled at Fordham University, but stayed just two years before heading to the Wharton School at the University of Pennsylvania. He graduated from Wharton in 1968 with a bachelor of science degree in economics.

Pictured here is Trump’s senior yearbook photo from 1964. Shortly after Trump declared his intent to run for the presidency, the New York Daily News ran the picture on its front page after Trump’s criticism of Sen. McCain. The paper mockingly called out the medals on Trump’s uniform, saying they were awarded for Trump “being neat” while at school.

 

Here’s Wharton College graduate Donald Trump standing beside his father, Fred Trump. Trump shared the endearing photo on his Instagram account. Fred Trump had continued the success of his own father’s company, building and selling “thousands of houses, barracks, and apartments” in New York City, according to Wikipedia. Three years after graduating from Wharton, Donald Trump would be named president of his father’s company, E. Trump & Son. They would eventually rename it the Trump Organization. Donald Trump would set out to build upon his father’s success.

 

“#TBT With my father, Fred Trump, in Brooklyn,1975. A great Father’s Day gift—a stay at my 5 star hotel,” Trump wrote in this photo caption he shared to his Facebook page. It was a happy moment for the father and son business team. But trouble lurked in the background. The Trumps that year settled a lawsuit from the Justice Department that their company systematically discriminated against prospective renters who were African-American. The Justice Department alleged the Trump Organization had screened out people based on race and not economic status. This wasn’t the first time the Trumps settled a case of racial discrimination. The pair was sued in 1969 by the management of a property they owned in Cincinnati, Ohio. Fred Trump directed that lawsuit be “quietly settled,” according to news reports. Despite the setbacks, the business kept chugging along, and Donald Trump soon would find love…

 

In 1982, on Forbes initial richest Americans list, Donald Trump and his father were included with a combined estimated $200 million fortune. In 1976, Fred Trump had set up trust funds of $1 million for each of his children and grandchildren. Donald Trump has stated that he started his career with a “small loan of $1 million” from his father, though he would have had access to the fortune his father and grandfather had built. But if you thought Donald Trump would be happy with a measly $200 million fortune, you’d be wrong.

 

Donald Trump continued to accumulate a vast fortune throughout the 1980s, eventually securing a spot on Forbes’ billionaires list in 1989. Forbes reporter Jonathan Greenberg later revealed that he thought Trump was deceiving him about his family’s wealth in order to appear on the list. Trump’s ascent to the billionaire list was short-lived, unfortunately. Business losses kept him off the list from 1990 to 1995.

In the photo above, Trump shared a memory of his failed bid to build the New York City convention center. “#TBT As a young man when I proposed the Convention Center in New York City.”

 

As Donald Trump’s fortune grew, he aimed to etch his place in New York City history by helping to alter the skyline. For years, Trump pushed for the development of Trump Tower, which was eventually approved and built, with construction completed in 1983. This photo from Getty Images shows Trump holding a model of the Fifth Avenue complex where “one of the apartments will sell for $11 million and [Trump] claims four bidders – none of them Americans – are bidding for it.”

 

By 1978, Donald Trump had launched the Manhattan real estate business that would begin to make him a billionaire. Trump purchased a 50 percent stake in the rundown Commodore Hotel located next to Grand Central Terminal. The hotel was reopened in 1980 as the Grand Hyatt Hotel, in partnership with the Hyatt hotel chain. Trump wasn’t all business at the time, though. In 1977, Trump married Czech model Ivana Zelníčková. The couple would go on to have three children together but would divorce in 1992 following Trump’s affair with actress Marla Maples.

 

Here’s Donald Trump proudly holding his first-born son, Donald Jr., in 1977. Trump and his wife Ivana had two more children together, Ivanka, born in 1981, and Eric, born in 1984. While Donald Trump was happily married and growing his family, tragedy struck elsewhere. Fred Trump Jr., Donald’s older brother, died in 1981 due to his constant battle with alcoholism. The death of Fred would have an indelible impact on Donald, who would give up alcohol and cigarettes altogether.

 

In 1983, Donald Trump purchased the New Jersey Generals, a United States Football League team. That year, Trump managed to lure Heisman Trophy winner Herschel Walker to the USFL. Then in 1985, Trump landed Boston College quarterback Doug Flutie. However, the USFL would fold before the 1986 season after losing an anti-trust case against the more established National Football League, as well as Trump’s strategy of moving the league from its spring/summer schedule to compete directly with the NFL in fall/winter.

 

In 1988, Donald Trump established the Donald J. Trump Foundation, which initially was meant as a way to give away proceeds from Trump’s most famous book, The Art of the Deal. The foundation’s tax returns show it donated money to various healthcare and sports-related charities, as well as many conservative political groups.

In the above photo, Trump shared, “Here with my father Fred, back in 1980. My hero, role model, and best friend. #TBT”

 

After much bureaucracy, missing deadlines, and over-budgeting, the city of New York awarded Donald Trump a contract to renovate Wollman Rink in Central Park in June 1986. By December of that year, the renovations were complete, and Trump left his mark on the popular tourist attraction with his logo emblazoned on the railing encircling the rink, the Zamboni, and on the rental skates. Trump donated some profits to charity and other public works projects, according to Wikipedia.

 

Donald Trump’s father Fred passed away in 1999. At the time of his death, Fred Trump’s will divided $20 million among his surviving children. Above are Trump and his father standing outside the renovated skating rink in Central Park. Trump’s marketing team wrote in this Instagram post:

“#PresidentTrump with his father Fred #Trump at the Wollman Rink in #CentralPark, #NYC – in 1987. #POTUS45 #ThrowbackThursday #TBT”

 

Donald Trump’s second wife was Marla Maples. Trump first met her in 1989 and began a much-publicized affair with her while still married to Ivana Trump. Maples and Trump would have one daughter together, Tiffany – named after the famous Tiffany & Co. brand – in October 1993. Trump and Maples married two months later at New York City’s Plaza Hotel, which Trump had acquired back in 1988. He eventually sold the hotel in 1995, but not before transforming it from a three-star to a four-star accommodation.

 

Donald Trump shared this throwback picture of him and the kids in 2013, stating it was 20 years ago. Trump stands over Ivanka, Donald Jr., and Eric. Like their father, the three would grow up to inherit wealth and work in their father’s organization. It seemed the Trump family business was in good hands moving forward, but was it?

 

Here’s Donald Trump next to a model of “Television City,” a proposed vast commercial and residential complex in Manhattan’s Upper West Side neighborhood along the Hudson River. Trump hoped the project would headquarter NBC News and other television studios. The tall building model in Trump’s hand was a proposed 150-story tower as the area’s centerpiece. It would have been the tallest building in the world if approved. However, things didn’t go as planned.

First and foremost came criticism of the development of the area, with numerous architecture critics saying the entire idea was “woefully simplistic” and had “little connection to the varied pattern of streets” of New York. Additionally, people in the community disapproved of the plan after Trump nearly doubled the area of the original idea when it was first presented. It further spiraled out of control when Mayor Ed Koch agreed to provide tax breaks to NBC if it moved its studios there, but not to Trump himself. In characteristic Trump fashion, this boiled over into tabloid fodder name-calling.

 

If there’s an image of Trump finally branching out from the umbrella that his grandfather and father had put up, it might be this one. Trump is seen here just after the New York Board of Estimate approved a plan for Trump to purchase and refurbish the abandoned Commodore Hotel in Manhattan. This was the purchase that allowed Trump to launch his real estate business, according to Wikipedia. Of course, it would be unfair to say Trump truly ventured out on his own.

The $70 million construction loan was guaranteed jointly by Fred Trump and the Hyatt Hotel chain (which would get its name on the building after the reconstruction). Though Trump continues to this day to claim he built the company himself, it’s more accurate to say he simply continued the success his grandfather and father had before him.

 

The same year Trump’s Commodore Hotel takeover was finalized, the city approved the rights for Trump to develop Trump Tower in Midtown Manhattan. In order to complete the tower, Trump reportedly hired undocumented Polish workers to demolish the old Bonwit Teller retailer flagship store. That building was well known for its art deco features and had originally been marked for preservation by the city.

Trump Tower took four years to complete (pictured here is Trump at the building’s “topping off” ceremony), with the final spaces opening by November 1983. The building holds numerous residential and commercial spaces, most notably Trump’s own penthouse condominium and headquarters for the Trump Organization.

 

Here is Trump and his friend and lawyer, Roy Cohn, at the opening of Trump Tower in 1983. Cohn and Trump have a long and interesting history together. First, Cohn represented Trump in a federal lawsuit against the Justice Department where Trump was accused of violating the Fair Housing Act at 39 of his properties by quoting different rental terms, conditions, and making false “no vacancy” statements to African American tenants in efforts to keep them from renting at his properties. Cohn’s countersuit against the DoJ was unsuccessful and Trump settled the charges out of court in 1975. Trump would be back in court again in 1978 for violating terms of the 1975 settlement.

But it was wasn’t only legal aid that Trump sought from Cohn. It’s been said that Trump emulates Cohn’s brash public “counterattacks.” That might explain why Trump loves to provide comments to the press, both positive and negative, of his perceived opponents.

 

In this 1984 photo, Trump is posing inside Trump Tower. In true Trumpian fashion, he told reporters, “What I have done is build the most beautiful buildings in the best locations.” Throughout the 80s, Trump would put his stamp on Wollman skating rink in Central Park and the Plaza Hotel in Manhattan. In the early 1990s, Trump would help refurbish the Gulf and Western Building on Columbus Circle in New York and the Bank of Manhattan Trust Building at 40 Wall Street, which was renamed Trump Building after an extensive renovation.

Additionally, Trump attempted to rename the Empire State Building when he began acquiring shares in the structure from 1994 to 2002. If he had been able to acquire a majority share, Trump intended to rename it “Trump Empire State Building Tower Apartments.”

 

This 1986 photo shows Donald Trump leaving a federal court. If Trump looks unhappy, that’s because he had just agreed to pay a $750,000 penalty to settle an antitrust lawsuit filed by the Federal Trade Commission. Trump had not notified the government before purchasing more than $15 million worth of voting stock in both Holiday Corp. and Bally Manufacturing Corp.

Even though it was a hefty sum, Trump at that time was riding the gravy train and things were going well for him. For Trump, these little setbacks in New York were easy to escape since he had come into possession of a sprawling estate down in Palm Beach, Florida. Many know it as the Mar-a-Lago estate these days.

 

Evidently unfulfilled with his New York City acquisitions, Donald Trump also began to put his signature thumb print on NYC’s neighbor, New Jersey. After the Garden State legalized casino gambling in 1977, Trump looked to move in for some business opportunities. In 1984, Trump opened Harrah’s at Trump Plaza hotel and casino. Through the mid to late 1980s, Trump would purchase several more casino properties in Atlantic City, acquisitions that would ultimately prove to be financially disastrous. (In the above file photo, Trump gives an interview at Trump Tower on April 4, 1985.)

 

This photo shows Donald and Fred Trump with then-New York city Mayor Ed Koch in July 1982. The trio looked delighted, but in just a few years, Trump would be seeing red thanks to his attempts to get into the casino business in New Jersey. After acquiring several properties, it soon became clear the ventures weren’t going to turn a profit.

As Trump was acquiring properties in Atlantic City, poor financial performances began to mount and Trump was forced to restructure debt and sell off his money-losing airline, Trump Shuttle, as well as his mega-yacht, Trump Princess. By 1995, Trump consolidated all of his casino properties in N.J. (as well as one in Indiana) under Trump Hotels & Casino Resorts. THCR underwent bankruptcy restructuring in 2004 and 2009.

 

Trump’s gamble on Atlantic City casinos wasn’t the only failed enterprise he attempted in the state of New Jersey. Here is Trump shaking hands with Walt Michaels, who Trump had just hired as Head Coach for Trump’s United States Football League team, the New Jersey Generals. That’s right. Trump purchased the Generals in 1983. He hoped to help turn the league into a major contender with the more established National Football League. But Trump made one fatal mistake in trying to run the league.

Many of the teams were losing money, but it was at the behest of Trump that the league move from its regular spring/summer schedule to the fall/winter to directly compete with the NFL. The USFL filed an antitrust suit against the NFL, which it won, but was only awarded $1. It was essentially a “victory in name only.” By then, most teams could not maintain the costs of running their organizations, nor compete with the NFL’s fall schedule, and the league disbanded.

 

For those familiar with Donald Trump and his aesthetic preferences, they might recognize this as the interior to one of Trump’s many properties. Trump does love gold! However, this image of Trump and his first wife Ivana Trump was taken in St. Petersburg, Russia in 1987. Unless you’ve been living beneath a rock the last few years, you probably know that Trump has a long history with the Soviet nation.

The visit in 1987 was an exploration to develop a hotel in Russia. Trump had been invited by Ambassador Yuri Dubinin. Almost a decade later in 1996, Trump attempted more real estate development deals by submitting trademark applications. For years, Trump infamously asserted he had no business connections with Russia, but that was found to be false when it was revealed Trump had been pursuing a deal to build a Trump building in Moscow into June 2016. It’s also been found that Trump received considerable financial support following his bankruptcies in the 1990s from sources in Russia. This was corroborated by Donald Trump Jr., who said Russia made up a “pretty disproportionate cross-section of a lot of our assets. … We see a lot of money pouring in from Russia.”

 

Though Donald Trump has seemed to fall out of favor with Hollywood elites in recent years, he was once a prominent sight at red carpet events all across the country. And can you blame him? He has been a staple of New York’s wealthy elite class since his birth. Trump has appeared in numerous films dating back to 1989, almost always as himself. Of course, his flirtations with TV and movie stardom hit its peak in 2003 when NBC brought on “The Donald” to host The Apprentice.

The reality TV show became a huge hit and helped Trump coin his catchphrase, “You’re fired.” The original show spawned the spin-off The Celebrity Apprentice. It seemed that Trump was once again rubbing elbows with Hollywood elite, but some of those connections have lingered, much to Trump’s dislike.

 

While Donald Trump these days often rails against celebrities who are critical of his governing style, it wasn’t always this way. While Trump has distanced himself from some famous people over the years (the Clinton family is a notable one), Trump’s connections to a former friend has come back into the spotlight.

Pictured here in 1997 are Trump and Jeffrey Epstein at Trump’s Mar-a-Lago resort in Florida. Trump and Epstein were friends for at least more than a decade, with Trump once telling New York magazine, “I’ve known Jeff for 15 years. Terrific guy. He’s a lot of fun to be with. It is even said that he likes beautiful women as much as I do, and many of them are on the younger side. No doubt about it — Jeffrey enjoys his social life.” Now though, Trump may wish he never made that comment…

 

Trump’s claim about Jeffrey Epstein liking women “on the younger side” has been heavily scrutinized in 2019 after Epstein was arrested in July 2019 for sex trafficking of minors in both Florida and New York. Rumors of Epstein’s pedophilia had swirled for decades. Trump and Epstein often partied together at Trump’s Mar-a-Lago estate, as seen here in 2000 sandwiched between Trump’s then-girlfriend Melania Knauss and British socialite Ghislaine Maxwell.

Trump and Epstein would have a falling out, however. The two wealthy financiers entered into a bidding war in 2004 for the Maison de l’Amitie, or House of Friendship. The oceanfront Palm Beach property was highly coveted and it was Trump who outbid the competition, which seemed to upset Epstein enough that they no longer spoke. Just four years after purchasing the property, Trump would sell the estate to Russian businessman Dmitry Rybolovlev.

 

This official portrait for Donald Trump from 1983 takes us back to the years before he was in the headlines every day. This was the year after Trump landed on the inaugural Forbes list of wealthy individuals, since he had a share of the Trump company’s $200 million estimated fortune. His 1980s losses would cause him to fall off the list, but as we’ve seen, he made a comeback.

Forbes‘ most recent ranking in 2019 estimated Trump’s net worth at $3.1 billion (259th in the United States). He was the first billionaire president. However, Forbes does claim that Trump’s wealth fell 31 percent since the time he announced his presidential run. Whether that trend continues or reverses will be determined in the years to come.

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