Candid old photos of Donald Trump and his family through the years
Take a glimpse inside the powerful and glitzy clan
Say what you will about Donald Trump – the meteoric rise of his kin from humble immigrant stock to outrageously rich real estate moguls, world-famous reality TV stars and America's First Family has been nothing short of jaw-dropping. Explore these archive pictures of the Trump family history, from an army-dodging German grandfather to his life with Ivana, Melania and the next generation of the Trump clan coming up through the ranks...
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The early years: Donald Trump's grandfather Frederick
Frederick Trump was born in the Bavarian village of Kallstadt to a hard-up family on 14 March 1869. After training as a barber, the youngster immigrated to New York City at the age of 16, to dodge military service and find work. This pic was taken when he was around 18. In 1891, he moved out West and went on to make a tidy sum dabbling in real estate and operating hotels, restaurants and brothels during the Klondike Gold Rush.
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The early years: patriarch Frederick Trump's brood
Frederick returned to Germany in 1901 where he married Elisabeth Christ, but ended up being stripped of his citizenship for evading the draft. The couple made their way back to the US in June 1905, settling in New York City. Frederick started a property business and the couple had three children: Elizabeth, Donald's father Fred, born on 11 October 1905 (left in this pic from 1915), and John, who would go on to become a distinguished MIT physicist and engineer.
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The early years: Donald Trump's father Fred
Donald once said he'd never heard of anyone dying from the flu, yet his grandfather Frederick was one of the millions of victims of the 1918 Spanish flu epidemic. Following the Trump patriarch's death, Elisabeth took over the running of the burgeoning family real estate business and was later joined by her son Fred. Blessed with a talent for property developing, he'd built 20 homes in Queens by the age of 21.
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The early years: Donald Trump's mother Mary
The company that would morph into the Trump Organization was incorporated in 1927, and went from strength to strength with Fred at the helm. Here's a photo from 1935 of Fred's wife Mary, who met her husband at a dance not long after she'd immigrated to the US from the Isle of Lewis in Scotland. The couple tied the knot in 1936 and set up home in a Tudor-style house in the leafy Jamaica Estates neighbourhood in Queens.
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The early years: Donald Trump's arrival in the world
Fred became ever more successful and eventually owned and operated 27,000 apartments in New York City, though his career was marred with accusations of racism, profiteering, tax evasion and other unethical practices. In the meantime, he and Mary had five children: Maryanne, Fred Jr, Elizabeth, Donald (born on 14 June 1946) and Robert. To quote the caption Donald wrote when he posted this pic of himself at four-years-old on Facebook: “Who knew this innocent kid would grow into a monster?”
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The early years: Donald Trump's siblings
Around the time that photo was taken, the family upgraded to a mansion in the same swish Queens neighbourhood. This shot shows the Trump siblings likely sometime in the early 1950s. Donald is standing on the far left, beside older brother Fred Jr, Elizabeth, Maryanne and Robert.
The early years: Donald Trump's schooldays
Trump attended a posh private school in Queens from kindergarten through to eighth grade, but was packed off by his father to a tough military academy at the age of 13, to deal with his atrocious behaviour. Donald himself alleges his wayward actions included punching a teacher in the face; he is pictured here, second from the left at a friend's Bar Mitzvah.
The early years: Donald Trump's high school yearbook
More sporty than cerebral, Donald joined every team going, from baseball to football and wrestling, captaining several of them, and actually thrived under the regime of strict discipline. The boarding school's harsh rules didn't stop him from meeting girls though, with his room “a revolving door” on Sundays, when young women from “the upper levels of New York society” would come to visit. No wonder Trump was voted "Ladies' Man" in his 1964 high school yearbook.
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The early years: Donald Trump's high school graduation
Donald is pictured here together with his proud parents Fred and Mary in the spring of 1964, in the grounds of the New York Military Academy. His niece Mary has claimed he got a brainier kid to take the SAT for him, which may explain his suspiciously high score. After graduating from the academy, Donald toyed with the idea of going to film school and becoming an actor, but decided he'd make more money in property.
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The early years: Donald Trump's college days
Armed with that high SAT score plus an ambition to dominate the New York property market, Donald enrolled at Fordham University to pursue a BSc degree in economics with a concentration in real estate. Here he is, second from the right with members of the college squash team. The institution wasn't for him, however, and he dropped out after two years to study the same degree at the University of Pennsylvania's prestigious Wharton School.
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The early years: Donald Trump's grown-up siblings
Donald graduated in 1968, though without honours; he certainly didn't come top of the class, as he has claimed. This photo appears to have been taken around the time of the graduation. Donald is seated second to the right next to his sister Maryanne, who went on to become a federal judge. On the far left is future investor Robert, next along is banker Elizabeth, with Fred Jr standing in the middle. He tragically descended into alcoholism and died at just 42 years old.
The real estate mogul years: Donald Trump's career begins
Fred Jr's daughter Mary has since claimed Donald, Maryanne and Robert duped her out of the millions she should have inherited. Post-graduation, Donald was diagnosed with bone spurs, which led to his medical exemption from the military during the Vietnam War. He started working for his father and in 1974 became president of the companies that would become the Trump Organization. With decent money flowing in, Donald moved into a three-bedroom Manhattan penthouse at 160 East 65th Street, shown here in 1976.
The real estate mogul years: Donald Trump meets Ivana
Still, Donald's salary in 1976 reportedly amounted to a relatively modest $70,000 (£57k) – the big money would come later. That same year, the up and coming realtor met Czechoslovakian model Ivana Zelníčková at an exclusive Manhattan restaurant, where she was standing at the bar with a group of fellow models waiting in vain to be seated. Donald pulled some strings, got the group a table and hit it off with Ivana. The pair started dating soon after. This candid photo is included in Ivanka's book, Raising Trump.
The real estate mogul years: Donald Trump marries Ivana
Around this time, Donald was moving the focus of the family business away from downmarket rental homes to luxury hotels and residential properties. Assisted by gifts and loans from his father and generous tax breaks, he bought the rundown Commodore Hotel in Manhattan in 1976 and reopened it as the lavish Grand Hyatt. The following April, Donald and Ivana walked down the aisle.
The real estate mogul years: Donald and Ivana Trump's honeymoon
The happy couple are shown here on their honeymoon, looking as loved-up and carefree as could be on that sunny beach. Donald was soon back at work expanding his real estate empire, however, while Ivana was hired as an interior design consultant. She would work on various projects over the years, before taking on executive roles at the Plaza Hotel in Manhattan and Trump's Castle Hotel and Casino.
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The real estate mogul years: birth of Donald and Ivana Trump's first child
The power couple's first child, Donald Jr, was born on 31 December 1977. Here he is in his father's arms sometime in early 1978. Donald's career continued to blossom, and in 1979 the family went up even further in the world, moving into a plush apartment in the ultra-high-end 800 Fifth Avenue building.
The real estate mogul years: Donald Trump Jr and his parents
The young family-of-three are seen enjoying some quality time together in this pic, which appears to have been taken around 1980. Meanwhile, Donald had announced his most ambitious project yet, the magnificent Trump Tower on Fifth Avenue, and construction work was getting underway on the 58-storey skyscraper.
The real estate mogul years: birth of Ivanka Trump
Donald and Ivana's second child was born on 30 October 1981, christened Ivana, after her mother, but nicknamed Ivanka from an early age, a moniker which stuck. A year after their daughter arrived in the world, Donald and Ivana dropped $4 million (£3.2m) on a stunning mansion in Greenwich, Connecticut.
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The real estate mogul years: Trump Tower completion
Trump Tower was completed in 1983 and the family moved into the jaw-dropping triplex penthouse atop the building. Donald and Ivana are pictured here with former New York City mayor Ed Koch at the skyscraper's opening party. Dripping in marble with flashy gold accents throughout, the glitzy tower wowed New Yorkers with its opulent apartments and five levels of restaurants, galleries and high-end stores like Cartier and Loewe.
The real estate mogul years: young Ivanka Trump
Donald is shown here possibly around 1985 with his young daughter at a birthday party. A year before, the real estate mogul and his wife welcomed their third child, Eric, who was born on 6 January 1984. It was around this time that Donald began investing heavily in the casino business in Atlantic City.
The real estate mogul years: Donald Trump buys Mar-a-Lago
Donald pulled off the real estate coup of the decade in 1985 when he acquired the spectacular Spanish-Moorish Mar-a-Lago estate in Palm Beach for a bargain $8 million (6.5m), a fraction of what it was worth at the time. Ivanka was spoilt rotten with the property's Sleeping Beauty-inspired bedroom, a fairytale-like suite designed for the original owner's daughter.
The real estate mogul years: Donald Jr, Ivanka, Eric Trump and their parents
This snap of the family of five posing on a spiral staircase was taken in 1986, when Donald and Ivana were becoming increasingly famous, hanging out with A-list celebrities and featuring regularly in the tabloids. The publicity-hungry property magnate was also getting very rich indeed, with several large-scale developments from Trump Tower to Trump Parc under his belt, along with two Atlantic City casinos.
The real estate mogul years: Donald Jr, Ivanka and Eric Trump
Donald and Ivana's three kids are shown fooling around in this photo, which looks like it was taken around the same time as the previous snap of the family posing on the staircase. As you might have expected, all three attended top private schools all the way through, from elementary to high school.
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The real estate mogul years: the Trumps' Connecticut mansion
In 1987, Donald and Ivana invited the press for a tour around their eight-bedroom Greenwich mansion, offering an eye-popping insight into their extravagant lifestyle. The manse was decorated in Donald's favourite Louis XIV style: think copious gold leaf, enormous crystal chandeliers, extravagant frescoes and statues galore.
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The real estate mogul years: the Trumps' Connecticut mansion living room
While not as out-and-out flashy as the entrance hall, the living room is nonetheless very fancy, with the crystal candelabras and other pricey knick-knacks adding a glam touch. That said, the room – like the other spaces in the mansion – has a strong 1980s vibe, despite being packed with antiques and reproduction furniture.
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The real estate mogul years: the Trumps' Connecticut mansion kitchen
The couple had become wealthy enough by this point to afford a coterie of staff. They are pictured here with their personal chef, tasting what looks like a yummy tomato sauce in the mansion's homely yet luxe kitchen. While antique in style by and large, the kitchen has that unmistakable 1980s feel.
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The real estate mogul years: the Trumps' Connecticut mansion verandah
The verandah looks even more indicative of the time, with the fussy rug, bizarre parrot sculpture and those wicker sunbeds decked out with chintzy cushions. Despite the now-dated decorn, the space is kind of idyllic and has the loveliest view of the mansion's garden and Long Island Sound.
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The real estate mogul years: the Trumps' Connecticut mansion pool
Donald and Ivana ended the tour of their Connecticut manse at the fabulous resort-style pool, which is dotted with OTT statues to add to the ostentation. Ivana gazes lovingly at her husband in this shot, but it wouldn't be long before she'd be looking at him with a less-fond emotion.
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The real estate mogul years: Donald Trump's New York City office
Donald invited the press for a sneaky glimpse into his day-to-day work life, back in 1987. The high-powered businessman is pictured sitting at his desk talking away on the phone, no doubt cutting a money-spinning deal. Note the wall emblazoned with copies of Donald's magazine covers and that showy mirrored ceiling.
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The real estate mogul years: Donald Trump's New York City boardroom
Years before The Apprentice, Donald chairs a high-level meeting in the Trump Tower boardroom in this shot from 1987, looking stone-cold serious as he talks business with his top execs. In keeping with the head-honcho's penchant for all things blingy, the room is decorated with shimmery gold curtains that wouldn't look out of place in a nightclub.
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The real estate mogul years: Donald Trump's limo
A tireless workaholic, Donald is shown toiling away on the move in this shot as he talks on his limo's car phone. By this time, the real estate magnate had become quite the celebrity. Capitalising on his stardom, Donald released his first book, The Art of the Deal, in 1987. A major hit, it topped the New York Times Best Seller list for 13 weeks.
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The real estate mogul years: Donald Trump's private jet
A reflection of his growing fame and fortune, Donald went all out in 1987 and splashed $11.5 million (£9.3m) on a Boeing 727 jet, the first of several private planes the real estate mogul would own. Over the years, they would get bigger and more luxurious, with features like a regal standalone bedroom and bathroom adorned with 24-karat gold-plated fixtures.
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The real estate mogul years: Ivana Trump's CEO role
As we've mentioned, Ivana took an active role in the Trump family business and acted as CEO of the Castle, one of three hotels and casinos Donald owned in Atlantic City in the late 1980s. She is posing here in 1987 in the resort's snazzy atrium, which was decorated with gaudy gold castles sitting on mirrored columns.
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The real estate mogul years: Ivana Trump's business acumen
Ivana would have taken plenty of trips on her husband's private jets, given her role in the Trump Organization, which of course didn't just extend to the running of the Castle Hotel and Casino. She also oversaw interior design for numerous Trump buildings and managed the Plaza when it was voted America's best luxury hotel.
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The real estate mogul years: Donald Trump's yacht
By 1988 Donald had really arrived, with The New York Times pegging his net worth at an estimated $3 billion (£2.4bn), though Forbes put his fortune at a billion dollars. Absolutely rolling in it, the real estate and casino tycoon wasted no time bagging the ultimate billionaire plaything: a superyacht he named Princess. Donald snagged the $100 million (£81m) boat for a steal, paying its owner, Saudi arms dealer Adnan Khashoggi, $30 million (£24m) for the wow-factor status symbol.
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The real estate mogul years: Donald Trump's affair
Donald and Ivana may have looked happy in the previous pic, but their marriage was already on its last legs, since Donald was having a full-blown affair with model Marla Maples, who he'd met at a tennis tournament in 1985. The relationship fast became very public, and in the summer of 1989 Marla moved onto Donald's yacht.
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The real estate mogul years: Donald Trump's marriage and career downfall
This pic of Donald and a not-so-cheerful-looking Ivana was taken in 1990 in the Trump Tower penthouse apartment. Just as his marriage was going downhill, Donald's career began to hit the skids, creating the perfect storm of turmoil in his life. The real estate slump of the early 1990s battered the business, while several Trump casinos went bust. Donald's debts skyrocketed and the yacht and other assets were offloaded.
The real estate mogul years: Eric Trump's sixth birthday party
In spite of Donald's blatant affair with Marla Maples, he and Ivana didn't instantly go their separate ways, choosing instead to keep up a united front, presumably for the sake of their children. Here they are in January 1990 at Eric's sixth birthday party in Mar-a-Lago's ornate ballroom, looking like absolutely nothing was wrong with their marriage.
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The real estate mogul years: Donald Trump's total marriage breakdown
The end, however, was nigh. Donald filed for divorce not long after, and the process swiftly turned bitter and acrimonious. This photo from January 1991 captures what looks like a tense exchange between the couple, whose relationship – not helped at all by the lurid stories in the tabloids documenting every detail of Donald's affair – would have been at rock bottom.
The real estate mogul years: Ivana Trump's 1993 Thanksgiving with her kids
After Donald and Ivana's separation in 1990, the kids split their time between their parents, though Ivana fought hard for full custody in the courts, which she eventually won. According to The New York Times, she walked away with $14 million (£11m) and the couple's Connecticut trophy mansion. Ivana is basting the Thanksgiving turkey, with daughter Ivanka helping with the gravy, in this shot from 1993.
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The real estate mogul years: Marla Maples' pregnancy
The previous spring, Donald and Marla announced that she was expecting the couple's baby. Donald is proudly touching his partner's bump in this photo taken on 7 April 1993. At the time, Marla, who had been trying her hand at acting, was performing in the Broadway musical The Will Rogers Follies. She give birth to daughter Tiffany on 13 October 1993.
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The real estate mogul years: Donald Trump marries Marla Maples
A couple of months after the birth of their daughter, Donald and Marla got hitched at the Plaza hotel in front of a reported 1,000 guests. Despite this awkward pic, the wedding was hands-down spectacular. The bride wore a silk dress by Carolina Herrera, paired with a tiara worth an estimated $2 million (£1.6m), while the pampered guests dined on a gourmet spread of caviar, beef, smoked salmon and more.
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The real estate mogul years: Donald Trump's mother, wife and daughters
Donald's new wife was accepted with open arms by the Trump family, at least going by this pic taken in 1995, which captures Marla with Donald's mother Mary and the real estate tycoon's two daughters. At the time of the photo, Mary was aged 83, Ivanka would have been 14, Tiffany getting on for two and Marla 32.
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The real estate mogul years: Donald Trump's Mar-a-Lago Club
In order to drum up some much-needed capital, Donald had converted part of Mar-a-Lago into a private club in 1994, a move that turned the building into a highly lucrative sideline as moneyed members flocked to join. The flagging real estate magnate also bolstered the coffers by licensing out his name and brand, and it wasn't long before he was back to building major developments, investing in profitable ventures and raking in megabucks.
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The real estate mogul years: Tiffany Trump's childhood
This photo of Marla and Tiffany was taken on Manhattan's Fifth Avenue in 1995. In the early years of her life, Tiffany lived with both her parents, who divided much of their time between the Trump Tower penthouse in New York City and Florida's Mar-a-Lago, where the family could escape to their gorgeous private wing.
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The real estate mogul years: Tiffany and Ivanka Trump's cute relationship
Tiffany and her half-sister Ivanka appear to have a close, supportive relationship if their tweets and other social media messages to one another are anything to go by. And judging by this pic taken in the Trump Tower penthouse in 1996 and that other shot with Mary and Marla, the girls seem to have got on brilliantly from an early age.
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The real estate mogul years: Ivanka Trump's modelling career
Ivanka embarked on a part-time modelling career in 1996 aged just 14 after scoring a Tommy Hilfiger campaign. The Trump scion's modelling heyday was from 1997 to 1999, when she walked for big names including Vivienne Westwood and Thierry Mugler. This striking shot was captured at the designer's spring/summer 1999 show in October 1998.
The real estate mogul years: Donald Trump meets Melania Knauss
By this time, Donald and Marla's relationship had broken down completely and the real estate magnate was dating Slovenian model Melania Knauss, who he met at a party in September 1998. She is shown here at Mar-a-Lago with Donald, his sister Elizabeth and mother Mary. The pic was taken in 1999, the year Donald and Marla divorced.
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The real estate mogul years: Donald and Marla Trump divorce
Marla did pretty badly, since a bulletproof prenup restricted what she could get from Donald. She eventually received a million dollars, an additional million for a house and $100,000 (£81k) for Tiffany. Soon after, she moved with her daughter to California. Tiffany did, however, spend Thanksgiving 2000 at Mar-a-Lago, where she is pictured with Ivanka, Eric, Ivana's mother Maria and a cousin called David.
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The Apprentice years: Donald Trump's reality TV show
During the early 2000s, Donald worked on raising his media profile and hit the jackpot in 2004 when he was given his own reality TV show The Apprentice, which first aired in the spring of that year. The show proved a massive success, and according to Donald, earned him almost $200 million (£161m) over a 16-year period.
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The Apprentice years: Donald Trump marries Melania Knauss
Donald and Melania exchanged rings on 22 January 2005 at Mar-a-Lago, with Melania wearing a $100,000 (£81k) Christian Dior dress for the glittering ceremony. A total of 350 guests were invited to the $3 million (£2.4m) wedding, including Bill and Hillary Clinton, Anna Wintour, P Diddy, Billy Joel and Barbara Walters. They were treated to copious Cristal champagne, a $50,000 (£40k) Grand Marnier wedding cake, caviar, lobster and other delicacies.
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The Apprentice years: Donald and Melania Trump's son Barron is born
The couple's son Barron was born on 20 March 2006. He is pictured here with his parents at the men's final of the US Open on 10 September 2006, which would make him not much over five-and-a-half months in the pic. Like his siblings, Barron has attended the best schools and grown up amid immense privilege.
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The Apprentice years: Trump sibling colleagues
The three eldest Trump children all joined their father's real estate business after college, serving in senior positions in the Trump Organization. The trio also assisted their father in the judging process for The Apprentice show, sitting alongside their pa to offer their advice about who should be fired and who should stay.
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The Apprentice years: Donald Trump Jr's daughter is born
Donald Trump Jr married model Vanessa Haydon in 2005 and the couple welcomed daughter Kai in 2007. The couple would go on to have five children together. Following Kai, Donald III was born in 2009, Tristan arrived in 2011, Spencer in 2012 and finally Chloe in 2014.
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The Apprentice years: Ivanka Trump marries Jared Kushner
After dating and and off for four years, Ivanka Trump tied the knot with real estate developer Jared Kushner in October 2009, having cemented her commitment to the marriage by converting to his Jewish faith. The classy ceremony was held at the Trump National Golf Club in New Jersey. Ivanka wore a custom Vera Wang dress and the guestlist included Natalie Portman, Anna Wintour and Rupert Murdoch.
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The Apprentice years: the reality show's celebrity version
In addition to her Trump Organization position and the fashion line she'd created, Ivanka continued in her judging role on The Apprentice, which by this time had its format tweaked to become The Celebrity Apprentice, which debuted in the seventh season in 2008. In this pic from 2010, Donald Jr, Donald and Ivanka are congratulating season nine winner Bret Michaels as he hugs runner-up Holly Robinson Peete.
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The Apprentice years: Donald Trump's presidential bid
Donald announced his bid to become the leader of the free world on 16 June 2015 with a controversial speech and snappy Make America Great Again slogan that electrified the Republican Party base. The real estate mogul-turned-reality star-turned-presidential candidate roped in his wife, children and their spouses, along with the grandkids, for the launch event.
The Apprentice years: the Trump family's united front
Apart from Fred Jr's daughter Mary, the Trump family were solidly behind Donald's presidential bid and often joined the outspoken candidate on the campaign trail. In this photo from February 2016, Donald is enjoying a family dinner with Melania, his kids and their spouses, celebrating in all likelihood the success of his campaign and maybe even his personal wealth, which peaked at $4.5 billion (£3.6bn) in 2016, according to Forbes.
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The presidential years: Donald Trump in power
Donald defied the odds to win the November 2016 election, and his polarising presidency began the following January. Melania tended to keep a low profile but did join her husband to undertake traditional first lady duties when the need arose, like when Canadian president Justin Trudeau visited in October 2017.
The presidential years: Melania Trump's first lady role
While a reluctant first lady, Melania did get stuck in to her Be Best anti-cyberbullying campaign and oversaw the redesign of Jackie Kennedy's rose garden, as well as the White House Christmas decorations, for which she received her share of criticism. Melania is shown here in summer 2019 planning that year's holiday decorations.
The presidential years: Ivanka Trump's government role
Amid accusations of nepotism, Ivanka was appointed senior advisor to the president. She promptly resigned from her role in the Trump Organization and wound up her fashion line. Together with her husband Jared, who also landed a senior advisor position, Ivanka had her fingers in many White House pots and often sat in on high-level meetings, including this one with the Japanese Prime Minister Kenzo Abe in the Trump Tower penthouse in November 2016.
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The presidential years: Donald Trump Jr's divorce and new partner
Since Donald was running America, Donald Jr and his brother Eric were tasked with looking after the Trump Organization. On top of the stress of coordating an enormous network of companies, Donald Jr had to navigate a marriage breakup after his wife filed for divorce in March 2018. Donald Jr started dating Fox News host Kimberley Guilfoyle not long after the split and the couple are now engaged.
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The presidential years: Tiffany Trump's university days
Tiffany spent much of her father's presidency at college. Donald's youngest daughter enrolled in Washington DC's Georgetown Law School in 2017 and graduated in 2020, but would have enjoyed sojourns at her apartment in Manhattan, where this pic was taken in 2018. Tiffany has since relocated to Florida and is currently planning her wedding to fiancé Michael Boulos.
The presidential years: Eric Trump's wife and kids
Like Tiffany, Eric has been less visible than his siblings Donald Jr and Ivanka over the years, but has played an important role helping to run the Trump Organization and campaign for his father. Eric married Lara Yunaska in 2014 and the couple have two children, Eric Jr and Carolina.
The presidential years: the Kushners celebrating Hanukkah 2020
Nearing the end of their White House dream, Ivanka and Jared celebrate Hanukkah 2020 with their children Arabella, Theo and Joseph. Like several other members of the extended Trump family, Javanka and their kids moved to Florida after Donald left the White House, and have largely kept out of the public eye.
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The post-presidential years: the former first lady Melania Trump and her son Barron
Post-presidency pics of Donald, Melania and Barron are few and far between as the trio, like Javanka and their kids, lead a quiet life these days, mostly in Mar-a-Lago. Dodging the cameras, the former first lady and her son are exiting Trump Tower in this photo from last July. If Donald does decide to run in 2024, the entire family will doubtless thrust themselves back into the limelight, so they may want to relish their relative obscurity while it lasts.
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