From successful real estate deals to lending his name to all sorts of flop products to plans for a new social network, read on as we look at some of Donald Trump and his organisation's best and worst past, present and future business moves over the years. All dollar amounts in US dollars.

Aged just 24, Trump attempted to break into the Manhattan entertainment elite by investing $70,000 (£29k) to bag a co-producer’s position on the Broadway comedy Paris Is Out! It was an unlikely move at the start of a career in property. Despite good reviews, the play closed after just 96 performances.

Four years later, Trump made one of the best investments of his life. He bought the rundown Commodore Hotel for $10 million (£4.4m), and in six years turned it into the Grand Hyatt Hotel right in the centre of New York City. The 34-storey hotel remains a huge success and Trump cashed in his share of the property in 1996 for a whopping $142 million (£93m).

Trump was on a roll in 1974, enjoying a breakthrough after years of negotiating for an enormous residential complex on the Hudson River. The huge development included 25 acres of outdoor space and 5,700 apartments. He named the complex Trump Place, though after he was elected President residents at three of the complex’s 18 buildings successfully campaigned to remove his name from their facades.

In the early 1980s, Trump expanded his property empire with perhaps his most famous building, the 58-storey Trump Tower in Manhattan. He opened the lavish high-rise in 1983, complete with fine dining restaurants, shops and luxury apartments. It was, and remains to this day, highly-desirable real estate. By 1987, Trump claimed to have made $240 million (£155m) from apartment sales alone and millions more from restaurant and retail rent.

Trump’s business acumen took a huge hit when he bought the New Jersey Generals of the United States Football League (USFL) for $9 million (£6m) in 1983, losing $30 million (£20m) by the fall. Some even accuse Trump of folding the entire USFL. Trump’s lawyers filed a $1.69 billion (£1.1bn) lawsuit against the NFL over its monopoly of the TV networks. It backfired spectacularly, with the jury ruling that the NFL did have a monopoly but the USFL had caused its own downfall by overspending.

Two years later, Trump was back on track, buying the famous Mar-a-Lago resort in Palm Beach, Florida for just $5 million (£3.5m) after the market unexpectedly slumped. He turned it into a private club, built a $7 million (£5m) gold leaf ballroom and charged new members a $100,000 (£71k) initiation fee. In 2014 alone, Trump profited to the tune of $15.6 million (£9.6m) from the club. And the resort is one of only a few of Trump's business interests not negatively impacted by his presidency: Mar-a-Lago brought in $22.9 million (£16.5m) in 2020, up from $22.3 million (£16m) in 2015.

 

Back in the 1980s, Trump had quite the empire in Atlantic City, with the jewel in the crown being the Trump Plaza Casino and Hotel. Built for an estimated $210 million (£141m), the 32-storey Plaza opened in 1984 and was initially a bustling celebrity hotspot along the city's iconic boardwalk. In fact, the casino, which was visited by the likes of Madonna, Hulk Hogan, Mick Jagger and Oprah, was the most successful in the city at the time. But after closing its doors to the public in 2014, its final act was an explosive demolition in February this year. So how did a seemingly good business decision turn bad?

 

Trump had started building his Atlantic City casino empire by borrowing money at high interest rates, and when he opened another casino and started pouring money into the new Trump Taj Mahal rather than existing casinos such as Trump Plaza, the debt began to balloon. Just one year later Trump had $3 billion (£1.6bn) in debt, and ended up in the bankruptcy court for his Taj Mahal, Trump Marina, and Trump Plaza casinos. Four years later, having reorganised the casino holding company, Trump Entertainment Resorts missed another interest payment on a $53.1 million (£33.5m) bond, and had to declare bankruptcy again. But that wasn't the end of it...

In 2009, Trump Entertainment Resorts filed for Chapter 11 bankruptcy following the Great Recession. Then in 2014 the Resorts holding company was forced to file for bankruptcy again, which saw the closure of Trump Plaza, as well as the departure of Trump and his daughter Ivanka from the company's board. The company finally emerged from bankruptcy in 2016, and billionaire Carl Icahn's Icahn International company took over Trump's old Atlantic City properties, including the Taj Mahal, and the closed Trump Plaza. But even though he tried to have his name removed from the casinos, Trump doesn't see all of his work in Atlantic City as a failure. In fact, in a 2016 interview with The New York Times he boasted about the "growth" the city gave him, and how "the money [he] took out of there was incredible". Perhaps success is a question of perspective...

With over five million annual visitors, the famous Wollman Rink in Central Park stills pulls a healthy profit. Trump renovated the ice rink in 1986 after convincing then-mayor Ed Koch he could do it for $3 million (£2m). He actually finished the project $750,000 (£518k) under budget and by 2015 had made over $8.6 million (£5.7m) from the site. However, as mentioned earlier, Trump's contract with the rink is now ending. 

Trump has a lengthy list of 20 titles he has co-written including Surviving at the Top, his best-selling How to Get Rich and his presidential campaign book Crippled America: How to Make America Great Again. However, his writing career started in 1987 with The Art of the Deal. The book sold a million copies and remained on the New York Times best-seller list for 51 weeks. That said, since Trump's role as president his income from his books has fallen by a whopping 87% (between 2015 and 2020), according to Bloomberg.

Although his books proved entertaining, Trump’s board game Trump: The Game was, by all accounts, a failure. It launched in 1989 with the tagline, "It's not whether you win or lose, it's whether you win!" Trump starred in a TV commercial, anticipating it would sell over two million copies. It sold only 800,000 – which Trump put down to it being “too complicated” – and was pulled.

It seems that 1989 was not Trump’s year, with another fortune lost on a failed business venture: the Trump Shuttle. In an attempt to have his own slice of luxury air travel, Trump secured a $245 million (£150m) loan to buy air carrier Eastern Air Shuttle for $365 million (£224m). Within two years, and after a very expensive rebrand and upgrade, he was unable to make his $1.1 million (£630k) loan interest payments and the company lost $128 million (£73m).  

In his book Never Give Up, Trump described 40 Wall Street as one of his “favourite deals” – and it’s not hard to see why. Trump purchased the leasehold to this landmark address in 1995 for just $1 million (£632k). By 2015, Bloomberg valued that same leasehold at about $550 million (£363m). Trump was also receiving up to $30 million (£21.6m) a year in rent from tenants of the 72-storey building. However, the coronavirus pandemic has had a huge impact on the revenue the building generates, and the building has now fallen in value to $277.7 million (£200m). After some tenants have left or said they were considering leaving, loan documents show that Trump has offered rent concessions for people to stay in the Art Deco building.

In another unsuccessful departure from real estate, Trump trademarked two beers, a lager and an American pale ale, both of which failed to materialise into anything profitable. Despite this, he tried his luck in the beverage market again a few years later, with soft drinks called Trump Fire and Trump Power, neither of which got past the planning stages.

Before its closure in 2017, Trump Models had more than 100 women on its books, including Paris Hilton and Jodie Kidd, calling itself "the brainstorm and vision of owner, Donald Trump". With a $2 million (£1.5m) annual income from the agency and use of his models in episodes of his reality show The Apprentice, this was a successful business decision. However, the agency also became involved in multiple lawsuits, which were likely to have been costly. Former employees have made allegations that models worked without US visas, and lived in very poor conditions.  

Trump University is perhaps the most well-known and controversial of Trump’s business failures. In 2010, four former students sued Trump University for “offering classes that amounted to extended ‘infomercials’” and employing convicted felons as educators. The New York Attorney General sued Trump $40 million (£25.3m) for allegedly defrauding students. Trump tried to leave the incident behind, renaming the business The Trump Entrepreneur Initiative, but operations soon ended.

Premiering on NBC in 2004, The Apprentice enjoyed huge ratings across the US. Putting contestants through their paces as the business mogul host and executive producer of the show, Trump took home a huge $1 million (£556k) per episode. The show also did wonders for Trump's fame and brand worldwide.

Although he wasn’t directly involved with the business, Trump’s brand and wallet took a hit when he leant his name to a condo tower that went bankrupt. This was just one of many lost investments during the housing market crash. The Tampa developers declared bankruptcy with only $3,500 (£1.9k) in assets.

Built for $73 million (£41m), and now a combination of 5-star hotel and private residence, this 98-storey structure was supposed to be the tallest building in the world, but this was substantially revised after the September 11 attacks. Still, it was Travel+Leisure’s best large city hotel in North America in 2010, and in 2012 the 89th-floor penthouse alone sold for $17 million (£10.5m) – in cash. However, in recent years trouble has been brewing and the hotel's revenue fell from $26.2 million (£18.9m) in 2019 to $14.3 million (£10.3m) in 2020, likely due to the impact on travel caused by the coronavirus pandemic. Trump had tried to sell the hotel business before the pandemic, putting it on the market for more than $500 million (£360m) in 2019. But a sale seems far off, as after Trump's company apparently rejected bids "north of $350 million", its brokers actually walked away this January. And it’s not the only piece of real estate the former president has been trying to shift. During his stint in office, Donald Trump sold off more than $117.4 million-worth (£84.3m) of hotels and properties, according to Forbes.

Clearly Trump could renovate and run a highly successful hotel, but a travel website was a different matter. With the industry worth $80 billion (£57bn) a year, Trump sought his own slice of the cake by launching his GoTrump travel website. The experiment flopped, and the address now redirects to his current website.

When launching his mortgage business at the height of the housing market boom, Trump boasted to CNBC: “Who knows more about financing than me?” Yet the man Trump selected to run the business had worked on Wall Street as a registered broker for only six days. Trump’s anticipated first-year profits of $3 billion (£1.6bn) was quickly revised to $1 billion (£535m). With outstanding debts of $298,274 (£146,150) to a former employee and $3,555 (£1,745) owed in unpaid taxes, the entire enterprise was out of business by September 2007 as the housing market headed south. 

Unfortunately for Trump, 2006 was about to become one of his worst years in business. The complete failure of his first attempt at running a publication, Trump World, should have served as a warning of things to come. But ever the optimist, Trump re-launched the magazine as Trump in 2006, attempting to advertise luxury living even as the global financial crisis took hold. With $7.3 million (£4.6m) in debt, the magazine had folded entirely by 2009.

Trump’s brand took yet another hit in this shaky business move. Despite being teetotal and having no previous success in the alcohol business, Trump fancied his luck as the face of a vodka brand. As the slogan suggested, this was supposed to be “Success Distilled”. However, after poor sales the business folded five years later.

Next up he decided to launch a line of steaks. Strange move? Not when you consider that his beef was sourced from Buckhead Beef, to whom he owed $715,240 (£350k) after his Atlantic City properties filed for bankruptcy. Sales were abysmal and the company was discontinued, as was the Trump Steakhouse in Las Vegas due to 51 health code violations. 

Just before being sworn in to office, Trump made one of his biggest and riskiest purchases yet. He bought Turnberry Golf Course in Scotland for more than $60 million (£37m), spending a further $200 million (£123m) remaking the site. Turnberry lost $23 million (£18m) in 2016, with some questioning its ability to pay back the $300 million (£231m) owed in investment, let alone make a profit. In 2016 the New York Times reported that Trump tried to get a loan from Deutsche Bank to fund the works at Turnberry, using his Doral resort in Miami as collateral, but he was refused. And the issue with funding the project rumbles on. In February this year the Scottish parliament voted on whether there should be an investigation into Trump's financing of the project, but the politicians decided against it. Bad business move? Only time will tell. 

In 2015, the Trump Organization won the contract to run the Trump Golf Links at Ferry Point golf course in the Bronx. However, the 20-year agreement was terminated early this year because it had not attracted a major tournament to the course, according to the city. However, a spokesperson for New York City Mayor Bill de Blasio cited the riots at the Capitol in January as behind the decision too, saying: “Donald Trump directly incited a deadly insurrection at the U.S. Capitol. You do that, and you lose the privilege of doing business with the City of New York.”

The Trump Organization says it was never obliged to attract a tournament and in its suit said: “Mayor de Blasio had a pre-existing, politically-based predisposition to terminate Trump-related contracts, and the city used the events of January 6, 2021 as a pretext to do so.” Overall, the New York City contracts, which also include the carousel and two ice skating rinks in Central Park, are said to be worth $17 million (£12.25m) a year to the Trump Organization. Whether the suit turns out to be a good business decision remains to be seen...

Golf clubs and courses have proven incredibly lucrative for Donald Trump, and they generated around $943 million (£677m) over the course of his presidency. This accounts for the largest portion of his revenue during his tenure.

Trump's ultimate business success arguably came in January 2017 when he defied the odds to win the keys to the White House. Promising to run it like a business, he proved to be one of the most controversial presidents in history during his term and was impeached not once, but twice, the second time for inciting the violent siege at the US Capitol in January this year. Trump's poor performance in dealing with the COVID-19 pandemic, and failure of many of his proposals, including the completion of a US-Mexico border wall that had $15 billion (£10.8bn) of taxpayer money spent on it, means that he has left the role with a fairly negative legacy. And his personal finances have been impacted too, falling from $3 billion (£2.2bn) pre-White House to $2.3 billion (£1.7bn) today, according to a recent report by Bloomberg. And as he was acquitted both times he was impeached, currently nothing stands in his way of running for office again in 2024.

A new "communications" website Trump launched this year permanently shut down after less than a month. Following his permanent ban from Twitter and suspension from other platforms such as Facebook in early January after he was accused of inciting violence at the Capitol, Trump revealed his newsfeed-style blog – called From the Desk of Donald J. Trump – on donaldjtrump.com in early May as a "space to speak freely and safely". The website's closure came at the same time Facebook extended Trump's suspension from its platform for two years. There were reports that the blog had low traffic, which Trump called "wrong". He told his Desk followers to "stay tuned" for his new "platform". More on that later...

Trump has also launched a separate website for the offices of himself and the former First Lady, his wife Melania. Called 45office.com, the website has a long biography of the former president, heralding his success "dethroning political dynasties, defeating the Washington Establishment, and becoming the first true outsider elected as President of the United States...who put America first". It doesn't mention Trump's two impeachments. The website also allows you to ask the Trumps to attend an event, request a greeting, or just share your thoughts with the couple. While it's not clear how much the Trumps' attendance at an event might cost, it's likely it won't be cheap.  

At the beginning of July, the Trump Organization, Trump Payroll Corporation and the Organization's chief financial officer Allen Weisselberg (pictured centre) were indicted for a tax avoidance scheme alleged to have spanned more than 15 years.

The indictment alleged that, since 2005, the Trump Organization paid rent and other expenses for an apartment on Riverside Boulevard, New York, where Weisselberg and his wife were living, but Weisselberg didn't declare it on his tax returns so that he avoided paying New York City income tax. He is also alleged to have received tax refunds that he should not have been eligible for, and received $360,000 (£260k) for school fees. It's also alleged that Weisselberg orchestrated similar benefits for other executives at the company.

This means that Weisselberg has received $1.76 million (£1.3m) in indirect compensation from the Trump Organization according to the indictment. The three parties have all pleaded not guilty to the charges. Weisselberg has since been removed as officer of several subsidiaries of the Trump Organization, although reports suggest he will continue to be employed by the company, while Donald Trump Jr. (pictured right) has described the charges as a "political witch hunt". If found to be true, this could be a business decision that haunts Donald Trump. 

Trump has just announced plans to launch a new social media network called TRUTH Social. The network, which is expected to start its beta launch in November, is the first project of the Trump Media and Technology Group (TMTG). Trump has said that he "created TRUTH Social and TMTG to stand up to the tyranny of Big Tech", after his Twitter, Facebook, and YouTube accounts were suspended in the wake of the Capitol riots on 6 January. The former president – who had 88 million followers on his Twitter account alone – was known for his erratic tweeting schedule and use of Caps Lock, with his social media activity a key way of communicating with his supporters. His new network could be a very good investment as it will give him back an online mouthpiece and enable him to re-establish direct contact with his followers without fear of censorship. 

Now take a look at the products and brands Donald Trump loves