When former reality television host Donald Trump won The White House in 2016, the world was shocked. A man with no prior political experience, Trump was undoubtedly the underdog candidate — after all, in the Republican primary, he ran against storied politicians, including household names like Jeb Bush, Marco Rubio, and Ted Cruz. What was the former host of “The Apprentice” and the man behind the Miss USA competition doing on the debate stage? It was a question that many people did not take seriously until it was too late, and, in the blink of an eye, there he was, following Democratic nominee Hillary Clinton around a town hall debate like a shark luring for the kill.
In a shocking upset, Trump took over the presidency — by doing so, he sent one half of the country into uproar, while exciting the seeming minority of voters over his win (Trump lost the popular vote to Clinton by about 2.9 million votes, as noted by ABC News). But how did the real estate tycoon make it so far in politics? Here is the transformation of Donald Trump, from his time as a child and young adult, all the way to his post-presidency life.
Donald Trump was born to a patriarchal family with a demanding father, according to this insider
To know Donald Trump is to know his background. Before he was a player in the political game, he was a kid from a wealthy family with a rough childhood. Mary Trump, Donald’s niece and outspoken critic of the former president, told ABC News that Donald was born to a “sociopath” of a father, Fred Trump, who looked at his children as “expendable.” He told his children, reportedly, that they had to succeed and that they must “do anything to get attention, financial rewards, and to ‘win.'”
According to Mary, her father, Fred Trump Jr., did not subscribe to this understanding and was “punished for being kind.” But her uncle, Donald, embraced the toxic behavior and ran with it. “[Donald] clearly learned the lesson from watching his [older] brother,” Mary shared, before saying that the lessons he learned from his father during childhood stuck with him for life. “[Fred Trump] was incredibly driven in a way that turned other people, including his children [and] wife, into pawns to be used to his own ends,” Mary said.
As a young teen, Donald Trump was sent to military school, an environment where he thrived
We’ve all heard about problem kids being sent to military school, but, for Donald Trump, his time there lent itself to his demeanor. Donald’s father, Fred Trump, had decided to send Donald to military school at 13, and some former colleagues of the politician suspect that his relationship with his father greatly impacted his experience. “I strongly suspect that he had a relationship with his father that accounts for a lot of what he became,” Tony Schwartz, who co-wrote “The Art of the Deal” with Donald, said, as noted by PBS. “And his father was a very brutal guy … very, very little emotional intelligence, to use today’s terms.”
In line with his father’s wishes of unabashed success, military school was the ideal place for Donald to unleash his sense of dominance and brash behavior. “He talks about it as almost this, you know, rite of passage,” Timothy O’Brien, a Donald Trump biographer, said. “He said to me that when he arrived at the military academy, for the first time in his life, someone slapped him in the face when he got out of line.”
Donald Trump rode his father's coattails and made it big in real estate
We all heard the trope that Donald Trump got into the real estate market thanks to a “small” loan of $1 million from his father, Fred Trump, but we now know that the claim is far from the truth. As noted by The Washington Post, Fred was “one of the richest people in America in the 1970s,” and, as such, Donald received a number of benefits. After Donald graduated from the University of Pennsylvania in 1968, he joined his father’s real estate efforts in New York. He took over in 1971, and, just three years later, he was afforded a $40 million inheritance.
Michael D’Antonio, who wrote a biography on Donald Trump, told The Washington Post that Donald’s claim about his small loan is simply untrue, and it was thanks to his father’s money and connections, instead, that Donald built a name for himself. “When he wanted to go into business on his own, his father’s credit was available to him, and that was worth tens of millions of dollars,” D’Antonio said. A number of risky real estate deals paid off, and Donald started to create the reputation of a businessman and power player.
In 1977, Donald Trump got married for the first time
For a man beloved by conservative folks, Donald Trump has lived a pretty scandalous life, especially when it comes to his marriages. But let’s go all the way back to 1977, when Donald became a husband for the first time. After a “whirlwind courtship,” Donald married Ivana Trump, a former model and member of New York’s most elite social circles.
The union solidified Ivana’s place as a woman of substance and influence, and, as noted by Biography, she played an integral role in Donald’s business life. She worked as an interior decorator on a number of real estate ventures and even served in different executive roles at properties that included the Plaza Hotel in New York and the Castle Hotel and Casino. That’s not to say, however, that the marriage was healthy.
After having three children together, Donald and Ivana called it quits in 1990 — after rumors began circulating about Donald’s affair with actress Marla Maples. By the time the two split, according to Biography, Ivana walked away with a $20 million settlement and a name that could get her in just about any door she pleased.
Donald Trump emerged as a popular figure in the 1980s despite major business setbacks
As Donald Trump’s reputation within the real estate market began to grow, he ventured into other projects. Trump attempted to expand his career in the 1980s by getting involved with sports management. He did not, however, transform into the likes of Mark Cuban — who owns the Mavericks NBA team — but, instead, fell flat within the realm of sports investments.
As reported by The Washington Post, Trump purchased the New Jersey Generals, a football team that existed within the short-lived United States Football League (USFL), in 1984. Why would Trump opt to buy a team in a league that wasn’t the NFL? Apparently, he was hopeful that the USFL would be purchased by the NFL, just as the American Football League was in the mid-1960s. But, despite his hopes that the leagues would join forces, the USFL simply didn’t get off the ground, and the loss served as a pretty decent blow to the real estate figure. Biographer Michael D’Antonio said of the business setback, “I think he’s very good at real estate, I don’t think he’s very good at other things.”
Donald Trump flirted with a possible presidential run during an interview in 1988
A number of people were surprised when Donald Trump announced his presidential campaign in 2015, but he’d actually been teasing a presidential run for years. In, perhaps, another attempt to transform from a businessman to a politician, Trump spoke about the possibility of holding public office all the way back in 1988.
During an appearance with Oprah Winfrey, Trump said that while he “probably wouldn’t” run for president, he was getting “tired” of witnessing what was happening to the United States. “I would never want to rule it out totally, because I really am tired of seeing what’s happening with this country, how we’re really making other people live like kings, and we’re not,” he said, as noted by NPR. When asked if he thought he would win, Trump was emphatic: “I wouldn’t go in to lose. I’ve never gone in to lose in my life.”
He went on to tell Oprah that he would have a good chance of winning because “people are tired of seeing the United States ripped off” and that he would be the president to bring money back to people’s pockets. “It wouldn’t be the way it’s been, believe me,” he said.
Donald Trump turned into a failed airline mogul in the late 1980s
While Donald Trump was building a reputation as a mega-successful real estate mogul living the high life in New York City, he was also experiencing a number of business failures, including the Trump airline. As noted by Rolling Stone, Trump committed to a $245 million loan in 1988 in order to acquire the planes and routes of Eastern Air Shuttle. In classic Trump form, he plastered his name across the planes, installed gold fixtures in the restrooms (okay, we know he, himself, didn’t do it personally), and expected the planes to transport workers between city hubs, including Boston, Washington, and New York.
However, Trump’s outlandish branding and monetary investment did not pay off, and, in the end, he was forced to abandon the efforts. As Rolling Stone pointed out, within two years of taking up the venture, he didn’t even have enough money to pay the $1 million monthly interest payment associated with the loan. He eventually gave the ownership to his creditors and moved on to his next venture.
Donald Trump was suspected of tax evasion in the 1990s
A lot of skeletons come out of the closet when people run for the presidency. It’s classic dirt uncovering that so many political operatives do — think of it as a war chest approach. But Donald Trump would absolutely not budge in releasing in tax returns, as many of his predecessors did, so dedicated journalists worked to uncover the hidden truth. As noted by an investigation by The New York Times, Trump “participated in dubious tax schemes during the 1990s” which included “outright fraud” that benefitted both him and his parents.
Based on confidential tax returns and uncovered financial records, The New York Times discovered that Trump assisted his parents in avoiding paying taxes, and, additionally, worked with his sibling to “set up a sham corporation to disguise millions of dollars in gifts from their parents.” As such, he developed a system that “undervalue[d]” the real estate projects belonging to his parents in order to “reduc[e] the tax bill when those properties were transferred to him and his siblings.” With all this hidden in his tax returns, it makes sense why Trump was coy in handing them over to the public.
Donald Trump turned to the Miss USA competition in the 1990s to evolve his branding
When you think of Donald Trump, you might think Twitter, real estate, or “The Apprentice,” but you also likely think of models. His third and current wife, Melania Trump, is a former model, herself, so his affinity for the type is clear. In another transformative step in his career, Donald went into the business of modeling and pageantry, and from 1996 to 2015, he served as owner of the Miss Universe, Miss USA, and Miss Teen USA beauty competitions (via BBC News). The models and the cameras and the glitz and glamour definitely seemed on brand for the 1990s-era Donald, who had made his taste for all things gold and glitzy incredibly clear.
But, of course, his time as a pageant owner was not free from controversy, and, in the time following his departure from the competition circuit, former pageant queens have come forward with allegations of predatory behavior on his part. Miss Teen Vermont 1997, Mariah Billado, recalled when she quickly slipped on her dress after realizing that Donald had walked into the women’s dressing room. Three more then-teen pageant participants backed up the story, as noted by Rolling Stone.
By the early 2000s, Donald Trump ventured into entertainment, this time in front of the camera
Donald Trump really seemed to live life in the fast lane — from real estate projects to casinos to golf resorts to everything gold-plated, it seemed that, at least on the surface, he had it all. Trump’s public persona was then projected even more onto the main stage when he signed on to “The Apprentice,” a show designed to critique the business chops of contestants hoping to make it big. “The Apprentice,” was soon followed by “Celebrity Apprentice,” with both shows running on NBC.
The programming made Trump even more of a household name than he already was, but, like Trump’s other ventures, things soon went downhill. As noted by The Hollywood Reporter, NBC was doing poorly, despite the show’s excellent ratings. To keep the businessman on camera, network executives reportedly paid $500,000 to the Trump Foundation as a gesture of goodwill. As reported by BBC News, Trump ultimately made $213 million as the host of 14 seasons of the show.
Donald Trump's failing business ventures brought him to bankruptcy court in 2004
When Donald Trump was running for president, many supporters credited his business chops as the factor that made him a suitable man for the job. But Trump’s business career really wasn’t all that fantastic, and, as noted by Rolling Stone, the early 2000s saw him fall on some significantly tough times. Trump’s poorly-performing Atlantic City, New Jersey, properties led him to file for bankruptcy three times, dating back as early as 1991. But, in 2004, he found himself in bankruptcy court for the Trump Plaza casinos, the Trump Marina, and the Trump Taj Mahal properties, where he faced a debt of about $1.8 billion — yes, billion, with a B — and if you thought that was bad, it gets worse.
After the 2004 bankruptcy, the Trump Hotel and Casino brand got a facelift and new branding as Trump Entertainment Resorts Inc. But, just four years later, the newly-minted corporation didn’t pay up on the interest of a $53.1 million bond, and, as such, the company declared bankruptcy again. In the aftermath, Trump resigned his position as chairman. We’re not financial experts, but this does not sound good.
In 2005, Donald Trump married model Melania Knauss, his third wife
Donald Trump has been married three times, with one of his unions the result of an affair. After Donald and his second wife, actress Marla Maples, separated, a new Mrs. Trump soon entered his life. In 2005, Donald married model Melania Knauss, and, as noted by The New York Times, the wedding was outlandish and accompanied by a lot of Cristal champagne. The couple got married in the $42 million ballroom of the Mar-a-Lago beach club in Palm Beach, Florida, which boasts moldings made of 24-karat gold and a marble floor stretching 11,000 square feet. The seven-tiered wedding cake was truly the icing on the evening, and, from the outside, it seemed that the marriage was what the “Real Housewives” truly dream of.
The couple went on to have their son, Barron Trump, but once their relationship was projected into the political spotlight, truths about its status began to emerge. As People reported in 2021, the third Mrs. Trump has the relationship “down to a science” and uses her time to focus mostly on her son and her own professional projects. The former first lady is also very private, and it seems that she’ll stay that way.
One of Donald Trump's worst business failures came in 2006
For those of us in our mid-to-late 20s, we can distinctly remember the stress and worry that our parents experienced during the 2007 economic crash. Known as the Great Recession, the economic instability made unemployment skyrocket, resulting in numerous foreclosures and evictions, not to mention the crippling automotive industry. It seemed like everything came to a halt, but, just a year prior, Donald Trump thought it would be a great idea to establish his own mortgage company.
As noted by Time, the year 2006 saw one of Trump’s worst business dealings, despite his goals of establishing the country’s premiere home-loan lender company. After holding a press conference to announce the business, Trump spoke to CNBC about the decision. “Who knows more about financing than me?” he asked. Just a year and a half later, on the tails of the economic collapse, the mortgage company that he had created with his son, Donald Trump Jr. — who isn’t shy to share his opinion regarding vaccine mandates in New York — came to a crashing halt. And, as it turns out, the man whom Trump had chosen to operate the loan company was just a low-level broker who had only been in the mortgage business for six days. Oy.
Donald Trump emerged as a Democratic supporter in the mid-2000s
By the mid-2000s, Donald Trump had emerged onto the real estate scene, had evolved into a media personality, and had transformed into a public figure with a reputation for everything expensive. But what might surprise you to learn is that Trump was, at one time, also a fan of the Democratic party, and, in an interview with The Wall Street Journal in 2008, even claimed that his future nemesis, Hillary Clinton, would “make a great president.”
Yes, this is from the man who would make the former Secretary of State his public enemy No. 1, and, yes, we’re just as surprised as you are. Not only did Trump say that Clinton would make a good leader, but he praised her as a “very talented” public figure and even estimated that she’d be her party’s 2008 nominee for the presidency (the gig ultimately went to Barack Obama). “I know her very well,” Trump said during an appearance on CNN back in the day. “She’s very talented. And she has a husband that I also like very much. I think she’s going to get the nomination rather easily.” Things sure changed within a few years, that’s for sure!
Donald Trump transformed into a political figure and presidential candidate in 2015
While he had long flirted with the idea of a presidential run, Donald Trump shocked people when he actually decided to do it, announcing his intentions to run for office in 2015. Prior to his memorable ride down the escalator to formally kick off his campaign, Trump, at this point, had moved away from Democratic politics and had picked up the torch surrounding the Birther conspiracy. As noted by The Guardian, CNN’s Wolf Blitzer called the businessman out for his comments about then-President Barack Obama in 2012, but he doubled down on the idea that Obama was not born in the United States.
Trump’s campaign announcement continued to fall right in line with his chaotic brand. As reported by The Guardian at the time, Trump’s kickoff event included a slew of bizarre campaign promises (or, at least, they sounded so at the time), including building “a great wall” along the U.S./Mexico border. “Sadly the American dream is dead, but if I get elected president I will bring it back,” he said at the time. “Bigger, better and stronger than ever before.” Okay, Donald.
Donald Trump faced backlash for his comments and alleged actions toward women
As previously discussed, Donald Trump showed some allegedly troubling behavior during his Miss USA tenure, including roaming the dressing room of the pageant, but the allegations did not stop there. The New York Times detailed the stories of two women who accused Trump of assaulting them, one assault taking place over three decades ago, the other occurring in 2005.
Jessica Leeds — whose assault took place over 30 years ago — told The Times that while she was traveling on a flight to New York, Trump sat next to her and began touching her without her consent. Rachel Crooks, who was just 22 in 2005, alleged that she was forcefully kissed “directly on the mouth” by Trump while the two waited for an elevator. These are just two stories of the over 25 women who have accused Trump of sexual assault, and when the former president was questioned on the matter by a reporter from The Times, he lashed out with insults. “None of this ever took place,” Trump told the reporter. “You are a disgusting human being,” he reportedly said when questioned about the claims made against him.
In a surprising twist, former reality TV star Donald Trump won the presidency in 2016
We thought that Donald Trump’s campaign for president would be over after his debate performance that just about cut every other candidate off. We thought it’d be over after the “Access Hollywood” tape was leaked. We thought it would be done when his campaign was allegedly provided polling data by Russia. But it survived, and Trump transformed yet again from a political newbie to president — in quite the upset.
As noted by NBC News at the time, Trump won the necessary electoral college votes to clinch the presidency following the two-term service of Barack Obama. Calling his road to The White House “one of the most bitter and wildly unpredictable campaigns in the nation’s history,” NBC reported that Trump’s supporters were insatiably happy with the results. On the other side of the aisle, Hillary Clinton — who won the popular vote by about 2.9 million ballots (via ABC News) — conceded to the former reality star in front of a room of devastated supporters. “This is painful and it will be for a long time,” Clinton — who was a shoo-in for the presidency in just about every poll taken — said of the upset.
Donald Trump became the first U.S. president to be impeached twice
Donald Trump’s time in The White House was … eventful to say the least, from his midnight tweeting and un-presidential rhetoric to the misleading information from his administration — which was plagued with leaks to the press and questionable typos (long live “covfefe”). However, after a whistleblower report discovered that Trump had withheld military aid from Ukraine with the desire to get dirt on then-presidential candidate Joe Biden, things got ugly (via BBC News). Trump emphatically denied doing anything illegal during the phone call, but the report was enough for the House of Representatives to draw up articles of impeachment.
For the third time in U.S. history, a president — this time, Donald Trump — was impeached in the House. He was later acquitted by the Senate. Then came January 6, 2021, a day that truly lives in infamy. A “deadly mob” of Trump loyalists stormed the U.S. Capitol following a Trump rally, where the then-president told them, “You’ll never take back our country with weakness,” (via U.S. News & World Report). As a result of the “clear and present danger” posed from Trump’s presidency, he was impeached for a second time (via PBS). According to NBC News, four officers of the Capitol Police, as of publication, have died by suicide following the events of January 6.
If you or anyone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline at 1-800-273-TALK (8255).
Former President Donald Trump contracted the COVID-19 virus while in office
One of the defining events of Donald Trump’s time in office was the development and spread of the coronavirus. The COVID-19 pandemic halted just about everything — from indoor dining to social events to working in the office — leading the country (and the world) to shut down. But Trump downplayed the virus, as he had done from the start, spreading misinformation, and sending very mixed messages regarding mask wearing. As a result, this led to “tens of thousands of unnecessary deaths,” according to a study from The Lancet, and even Trump, himself, contracted the deadly illness while in office.
When it was announced that the then-president had come down with the coronavirus, it’s safe to say that a number of people weren’t surprised. A “superspreader event” had taken place at The White House just days before his positive test, according to BBC News. Due to the severity of the virus’ impact on his health, Trump was transported to Walter Reed National Military Medical Center, where his condition was, apparently, far worse than White House officials let on, according to The New York Times.
In 2021, Donald Trump found himself with no social media at his fingertips
From his early days as a real estate mogul to his outlandish time as the host of “Celebrity Apprentice” to his days in The White House, Donald Trump has been skilled in making a name for himself. After losing the 2020 presidential election to Joe Biden and being banned from social media platforms, including Twitter and Facebook, after supporting violent Capitol protestors, Trump has seemingly disappeared from the public eye and the headlines. As noted by People, Trump traveled to Mar-a-Lago in Palm Beach, Florida, following his one term in office. These days, apart from occasional email statements from his office — like this recent request to his supporters — along with mentions on Sean Hannity’s Fox News show, talks about his possible website launch, and a speech Trump gave at the North Carolina Republican Convention on June 5, 2021, he’s adjusting to a “dimmer sort of spotlight.”
So, what does the former real estate mogul’s life look like now? According to CNN (via People), Trump typically plays a round of golf every morning starting at 9 a.m., takes a break for a “leisurely lunch,” and spends the rest of the day catching up on the news and watching television, apart from occasional meetings with Republican leaders — a far cry from his 3 a.m. tweets railing against his political enemies and the press.
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