Former US president Donald Trump may be eyeing up another run for the White House in 2024, but before his political career took centre stage, the billionaire businessman accumulated a vast property portfolio, both for personal and business use. However, the Trump Organization, the real estate business that runs Trump Tower, various golfing resorts and his Mar-a-Lago estate, has just been found guilty of fraud on a massive scale. And it's just one in a series of legal challenges and accusations facing Trump's property empire...

On Tuesday, 6th December 2022, the Trump Organization was convicted of a 15-year criminal scheme to defraud tax authorities, providing ‘off-the-book’ benefits to top executives to evade heftier taxation. The case hinged on reams of spreadsheets and tax documents which were presented to presiding Judge Juan M. Merchan, who the New York Times reports had worked for several years as an internal auditor at a small real estate development company as a young man. 

After roughly 12 hours of jury deliberation over the course of two days, the Trump Organization was found guilty on all 17 charges, which included paying personal expenses, such as rent and car leases, for top executives, and handing out bonuses to independent contractors, all without reporting the income. These bonuses included luxury apartments and cars, exorbitant Christmas cheques, and even free cable television to compensate for lower salaries, enabling the Trump Organization to reduce its tax liabilities. Though Trump himself was not charged, prosecutors alleged that he was well aware of the criminal activities taking place within his organisation. According to a report in The Guardian, prosecutor Joshua Steinglass showed jurors a lease for a company-paid apartment with Donald Trump's signature and another memo Trump had initialled to authorise a pay cut for another executive.

Much of the case hinged on the testimony of Allen H. Weisselberg, the Trump Organization’s longtime chief financial officer, who was individually indicted. He pleaded guilty to the charge of devising the tax fraud scheme in return for a plea deal and will serve five months in prison. Prosecutors demonstrated that between 2005 and 2021, Weisselberg received just shy of approximately $1.8 million (£1.5m) in indirect compensation from the company. The Trump Organization has since released statements trying to pin the blame for the fraud solely on Weisselberg, who is currently on paid leave with the company. They said in a statement reported by The Guardian: "The notion that a company could be held responsible for an employee’s actions, to benefit themselves, on their own personal tax returns is simply preposterous."

Though Trump himself has not been charged, the verdict has obvious implications for the former president and self-professed master of ‘The Art of the Deal’. Trump built much of his previous political campaigns and public image on his financial success and supposed prowess as a businessman, an identity which has effectively been shattered by Tuesday’s verdict. Not only may the ruling damage Trump’s future political aspirations as he gears up for the 2024 election, but it will likely precipitate serious sanctions on his future business dealings as well.

Trump Organization financial executives must now await their sentencing date on 13th January 2023, and the organisation itself could face up to $1.6 million (£1.3m) in fines, the District Attorney’s office said on Tuesday. While a fine of that size would be effectively immaterial to a company of the Trump Organization’s magnitude, the conviction will likely heavily complicate the company’s ability to do business. However, Trump Organization lawyer, Alan Futerfas has said that the company plans to appeal the ruling on the grounds that "the criminal law governing corporate liability was vague".

To add to Trump's woes, New York Attorney General Letitia James filed a separate civil lawsuit on 21 September 2022 against the former president for a case of "staggering" fraud. She has alleged that Trump, along with his children and senior executives at the Trump Organization, "falsely inflated his net worth by billions of dollars" to secure bank loans on more favourable terms and gain tax benefits. Trump rebutted the accusations on Fox News, claiming: "This is just a continuation of a witch hunt that began when I came down the escalator at Trump Tower."

In a move that could see the end of Trump's real estate monopoly in the Big Apple, the lawsuit is seeking $250 million (£204m) in penalties, along with a permanent ban that would prevent Trump from running businesses in New York. One of the city's landmark buildings, Trump Tower, is among the 20 properties implicated in the allegations. The lawsuit states that Trump's personal triplex penthouse in the building was valued at an eye-watering $327 million (£268m) in 2015. However, not only was its size allegedly inflated, but the record sale in the building prior to its valuation was a mere $16.5 million (£13.5m), casting doubt on the "absurd" figure. 

 Also included in the civil indictment is Trump's Florida estate, Mar-a-Lago, which was valued at a staggering $739 million (£606m). According to Letitia James, this figure was based on the "false premise" that the land could be developed and sold for residential use, despite Trump signing away his right to do so. The club reportedly generated annual revenues of less than $25 million (£20.5m) and should have been valued at $75 million (£61.5m), James says. In August 2022, the estate was also the site of FBI raids, related to a separate criminal investigation into the mishandling of classified government documents.

Letitia James has also ruled that a watchdog should be appointed to oversee Donald Trump's real estate empire. Judge Arthur Engoron of the New York County State Supreme Court granted the preliminary injunction on 3 November 2022, which will see a court-appointed monitor chosen from a list of recommendations made by James and the Trump Organization. In the 11-page opinion, the judge said that the move was to "ensure there is no further fraud" before the lawsuit goes to trial.

As well as installing a watchdog, the injunction also prevents Donald Trump and the Trump Organization from transferring or selling assets without notifying the court and the New York Attorney General's office. The court-appointed monitor must also be given 30 days' notice before any restructuring of the Trump Organization takes place. Judge Engoron said the decision, which puts something of a chokehold on Trump's property empire, was necessary so that "defendants do not dissipate their assets or transfer them out of this jurisdiction". 

This comes a day after Donald Trump announced via his Truth Social platform that he was suing New York Attorney General Letitia James. A seeming retaliation to the $250 million (£221m) lawsuit James brought against Trump and his businesses, the former president accused her of carrying out a "war of intimidation and harassment" against him. The lawsuit itself, which was filed in Florida, alleges that James has a "stated goal of destroying him personally, financially, and politically." Let's look back at where the battle of the lawsuits started...

Other properties mentioned in the Attorney General's bombshell lawsuit include Trump Park Avenue, 40 Wall Street and Seven Springs in New York, Trump International Hotel and Tower properties in Las Vegas and Chicago, the former Trump International Hotel in Washington, DC, and a number of Trump National Golf Clubs across the US, including Jupiter, Doral and Westchester, plus Trump's Aberdeen and Turnberry clubs in Scotland. 

Let's take a look inside some of the properties implicated in the lawsuit...

From his childhood home to his New York estate, Donald Trump's real estate empire is vast and worth hundreds of millions of dollars. After setting his sights on Manhattan, Trump began the construction of Trump Tower in 1979. The 58-story skyscraper, which was previously a department store, houses luxury residential complexes as well as retail spaces, including Donald Trump's personal residence in the penthouse triplex.

Also the home of the Trump Organization's offices, the tower is famous for its all-out luxury décor. The reception area boasts 240 tonnes of pink white-veined marble with four gold elevators serving visitors only, and a private elevator reserved for members of the Trump family.

Until 2019, Trump Tower was the official main residence for the family. When Donald was elected president, he made the move to the White House in Washington, DC, while Melania and Barron stayed on until the teenager could finish school. After his presidential term came to an end, the Trumps' official residence became Mar-a-Lago, however, the former leader still stays at his penthouse apartment whenever he returns to New York. 

Often hidden behind closed doors, this rare photo shows a glimpse inside the penthouse suite. From the sparkling crystal chandeliers and 24-carat gold embellishments to the plush cream carpets, it shows Trump's penchant for luxury furnishings. Barron is said to have had his own floor of the building when they lived there full-time.

In 1985, after many years of trying to purchase it, Trump bought Mar-a-Lago for $8 million (£6.5m) including the estate and all its contents. A bargain price, it was much less than what Mar-a-Lago cost to build, with the estate said to be worth $160 million (£131m) in 2018 according to Forbes.

In the early 1990s, Mar-a-Lago was transformed into a members' club by Trump. As his empire ran into financial difficulties, Trump restored the mansion with a view to creating a cash cow by opening it up to fee-paying members. At the wish of Palm Beach Council, and to gain permission for his new project, Trump promised a sensitive restoration. Some of the estate's contents were sold off at auction to make money but were replaced with reproductions, including a jewel-encrusted marble dining table and Louis XIV chests. 

In typical Trump style, the restoration cost millions of dollars with a number of lavish additions including two swimming pools, a beauty salon, spa and a 20,000-square-foot ballroom. The Louis XIV-style space has $7 million (£5.7m) in gilding and each of the gold basins in the bathroom cost $100,000 (£82k) a pop. 

This fairytale room was the childhood bedroom of Dina Merrill, the previous owner of Mar-a-Lago and was also Ivanka Trump's bedroom. Named the 'Baby House', the décor was said to be inspired by Sleeping Beauty and boasts a silver-plated four-poster bed and an opulent fireplace surrounded by grand rose motifs.

Aside from Trump's private apartments, Mar-a-Lago offers members access to two dining rooms, a beach club, pool and spa and guest suites. In 2017 an Associated Press investigation found that Mar-a-Lago had 78 counts of health code violations in the last three years, which included a range of issues from mould in the ice machine to dirty cutting boards and even chefs serving unsafe seafood to guests.

During his presidency, Trump visited Mar-a-Lago 32 times, spending a total of 142 days there. However, these jaunts didn't come cheap, costing on average $3.4 million (£2.8m) each. His trips back and forth are said to have cost $13.6 million (£11.1m) in taxpayers' money in 2017. 

On 20 January 2021, the Trumps arrived at Palm Beach International Airport in Florida to head to their new official home at Mar-a-Lago. However, his permanent move didn't go down too well with his affluent neighbours according to CBS Miami. In December 2020, they sent a letter to the town council highlighting an agreement from 1993 that stops any club member from staying at the club for more than three weeks in a year. 

Since Trump's rocky exit as POTUS, he has also lost all his presidency perks. A helipad, which was installed at Mar-a-Lago with a temporary permit while he was president, has now been removed. It was the only one of its kind on Palm Beach, which has a strict 'no helicopter' rule.

After snapping up Mar-a-Lago, Trump bought his Seven Springs estate in 1996 for a reported $7.5 million (£6.1m). As always, a firm focus was on golf and Trump's aim was to build a Trump-branded golf course on the estate. However, plans were dashed by protests but despite the setback, Trump kept the property as a retreat for his family. 

Reached via a sweeping driveway and surrounded by manicured lawns, the 5,000-square-foot mansion boasts three swimming pools, a carriage house and 15 bedrooms. Surrounded by 230 acres of land, it would have made the perfect setting for Trump's proposed golf course. 

The grand interior, of course, follows the lavish style that the Trumps favour with marble floors, stone staircases and high moulded ceilings. Built in 1919 by Eugene Meyer, the chairman of the Federal Reserve, today the home is full of modern amenities including a bowling alley and two staff wings. 

The property reportedly took almost five years to build, with the help of 500 Italian masons and craftsmen, and it's been meticulously preserved over the years. One of the largest privately owned properties in Westchester, it's clear that Seven Springs holds a special place in the hearts of the Trump family. 

In October 2021, a bombshell rocked the Trump Organization when ABC News revealed that according to its sources, the golf course was the subject of an 'ongoing criminal investigation' by the District Attorney's office in Westchester, New York. According to USA Today, the probe centred around the organization's valuation of the Trump National Golf Course Westchester, following a successful six-month appeal to lower the club's taxes.

Donald Trump is shown here in the club's restaurant back in 2014, with his ex-wife Ivana, son Eric and his wife Lara. The Trump Organization's request to lower its tax liability on the Westchester estate was granted by a Supreme Court judge in August 2021, in a move that saved the club $155,000 (£127k) a year in tax going forward, as well as a substantial rebate of $860,965 (£706.7k). No charges or accusations of wrongdoing have been made at this time.

Pictured here is the 13th hole of the Trump National Golf Club Westchester. A representative of the Trump Organization told ABC News that a review of the club's tax assessments in 2021 was signed off by the town board, therefore "the suggestion that anything was inappropriate is completely false and incredibly irresponsible. The witch hunt continues." This is a separate case from the larger investigation into the Trump Organization being carried by the Manhattan District Attorney's office.  

That's not the only reason Westchester's been under scrutiny in past years. The golf club hosted the Eric Trump Foundation's charity golf tournament every year from 2011 to 2015, with the proceeds going to St Jude's Children's Research Hospital. However, the event caused controversy when it was revealed $200,000 (£164k) of donations went to other organizations with strong ties to Trump family interests, according to Forbes. A spokesperson for the Foundation said that relevant donors were made aware of where their money was going.

Ideally located by leafy Central Park in New York City, Trump Park Avenue is one of the jewels of Donald's portfolio. Dating back to the 1920s, the property was formally known as the Delmonico Hotel. Donald Trump purchased the prime piece of real estate in 2001 for a staggering $115 million (£94m) and set about renovating the building into one of the city's most luxurious apartment complexes.

The 32-story structure offers its residents elegant, upscale living, with a 24-hour doorman and concierge, a valet parking service, laundry service, daily cleaning service and a fitness centre. The building's entryway is typical of Trump's signature style, with rich wood panelling, dazzling chandeliers, a checkerboard floor and gold-effect elevator doors. Trump's eldest daughter Ivanka even purchased her first home in Trump Park Avenue, and it's seen many high-profile residents over the years. One tenant though would go on to cause the Trump Organization something of a headache. 

Pictured here is one of the building's duplex penthouse apartments, which originally hit the market for $45 million (£37m), before having its price slashed to $29.5 million (£24.2m)  in 2017. However, it was a resident in another of the complex's penthouses that got into hot water with Trump. In 2018, Trump Park Avenue sued a Saudi prince for $1.8 million (£1.5m) in unpaid rent. While he'd moved into the 7,132-square-foot unit in 2014, he'd reportedly stopped paying rent in 2017. In 2018, a Manhattan court ruled that the prince must repay the sum he owes.

In 2002, Trump National Golf Club snapped up this estate in Bedminster for a reported $35 million (£29m). Located 40 miles west of New York City in New Jersey, Trump immediately began transforming the club into a luxury club and golf course—it opened in 2004, just in time for that year's Fourth of July celebrations.

Spread over 600 rolling acres of New Jersey countryside, Bedminster offers no end of world-class amenities. It boasts a 36-hole golf course designed by renowned architects Tom Fazio and Tom Fazio II, a 16-acre practice facility, an indoor golf learning centre and even equestrian facilities.

Initial membership fees for Trump National Golf Club Bedminster are reported to cost around $350,000 (£287k)—and joining comes with lots of perks. As well as world-class golf, members also have access to a heated swimming pool, eight tennis courts, a basketball court, a state-of-the-art fitness centre and even a helipad for flying visits.

Members can also rent one of five luxury cottages or 11 suites during their stay. In 2020, plans were put forward for the construction of five new cottages and the expansion of an existing cottage to the township's land use board, though it's not clear if permission was granted or when work might begin. Ivanka Trump and her husband, Jared Kushner, reportedly have a home at Bedminster. The estate holds a special place in the couple's hearts after they wed within the grounds in 2009. 

Not just a corporate venture for Donald Trump, he also used Bedminster for presidential business too. Just two weeks after his election win in November 2016, he reportedly invited the club's wealthiest members to help him interview candidates for positions in his administration.

Bedminster was the location for his presidential coordination team, and Donald Trump has said it was an ideal location for coordinating business because it cost less to operate out of than New York. “I have a place there that costs almost nothing because it’s hundreds of acres and security, and they don’t have to close up streets," Trump said during a 2017 Fox News interview about his reasoning for staying at Bedminster. However, Trump's use of private, non-secure locations for official business often caused concerns regarding security on sensitive intelligence and influence on the administration.

While Donald Trump pushed hardline immigration policies throughout his presidency, the New York Times reported that the club employed people who were in the country illegally. Though there is no evidence that Trump or the Trump Organization executives knew of the two employees' immigration status, Amanda Miller, a spokeswoman for the Trump Organization, said in a statement provided to CNN. "If any employee submitted false documentation in an attempt to circumvent the law, they will be terminated immediately."

Since leaving the White House, Mar-a-Lago has been his permanent home, but when the Palm Beach resort closes from May through the summer, when hurricane season and stiflingly hot temperatures rock the region, Trump heads to New Jersey for the warmer months. In 2022, he reportedly moved all of his business dealings to Bedminister during this period, before returning to Mar-a-Lago for its fall reopening. 

Unsurprisingly, Donald Trump’s stays at his luxurious golf retreat have not been without controversy. On 7 July 2021, Trump held a press conference with executives from the America First Policy Institute to announce a class-action lawsuit against Facebook, Twitter, Google, and their CEOs, claiming that he was wrongfully censored. The former president was suspended from his social media accounts in January 2021 over public safety concerns in the wake of the Capitol riots, led by his supporters. However, judges dismissed his respective lawsuits against Twitter in May 2022, and Facebook in November 2021.

And there's been further controversy at the estate, as records released in July 2021 indicated that Donald Trump charged the Secret Service nearly $10,200 (£8.3k) for its use of guest rooms at his New Jersey golf club in May. The charges were for an 18-day stay—that’s about $566 (£464) per night at the resort. The Secret Service also released documents including a “hotel request” form that covered the period from 28 May to 1 July, as well as bills indicating $3,400 (£2.8k) worth of resort charges for January, February and early May.

The agency didn't disclose the reason behind those charges, which were placed before Trump’s arrival. The release of these bills came as New York state prosecutors announced criminal charges against the Trump Organization over its business dealings. The company and its chief financial officer Allen Weisselberg have now been charged with tax-related crimes. The criminal trial is scheduled for October 2022. Trump's Bedminster estate continued to make headlines throughout 2021... 

In January 2021, the PGA stripped Bedminster of its role as host of the 2022 championship tournament after the violent attack on the US Capitol carried out by the then president’s supporters. The organization tweeted: “Our feeling was given the tragic events of Wednesday that we could no longer hold it at Bedminster,” PGA CEO Seth Waugh told the Associated Press. “The damage could have been irreparable. The only real course of action was to leave.” Trump has held multiple campaign events at the Bedminster course over the years, including his appearance at a largely mask-free fundraiser in October 2020 held just hours before he announced his coronavirus diagnosis. 

In 2006, Trump purchased Balmedie, a 1,400-acre plot just north of Aberdeen, Scotland, with plans to turn it into yet another luxury golf course. However, turning the unspoiled stretch of coastline into a high-end golf course didn't run smoothly...

Just one of many hurdles for Trump to overcome, Scottish fisherman Michael Forbes, who had lived on his 25-acre farm his entire life, refused to sell his home to the billionaire. Located right in the middle of the planned second hole and hotel site, the real estate rebel was offered $408,000 (£335k) and a job on the golf course but still declined and refused to give up his home. 

The proposal faced more uncertainty when Aberdeenshire Council's Infrastructure Services Committee ruled against the plans in 2007. After an intervention by the Scottish government in 2008, Trump was finally given the go-ahead to start turning the ecologically sensitive site into a golf course.

Finally in October 2009 work on the site started and in 2012 it opened to the public. The billion-pound project includes two golf courses and a luxury 16-room hotel known as Macleod House. The estate reportedly cost Trump $60 million (£49m) to buy and a further $200 million (£164m) was spent on the new golf course. 

Formally known as the Doral Golf Resort & Spa, Donald Trump snapped up this 700-acre Miami property back in 2012 for $150 million (£123m) after it fell into bankruptcy. Swiftly renamed the Trump National Doral Golf Club, it was initially one of the Trump Organization's biggest money-makers, but in the past few years, the estate's fortunes have taken a turn for the worse. 

Prior to the pandemic when the 45th president was still the leader of the free world, the luxurious resort was reportedly bringing in over $70 million (£57m) a year, according to official financial disclosures he made while in office. However, over the next two years, following a divisive presidency and the introduction of global travel restrictions in the midst of the pandemic, that figure fell by more than $33 million (£27m), a colossal drop of over 40% in revenue. 

But signs of decline at the club have been clear for some time. In 2016, the PGA announced it was moving the World Golf Championship from the Doral resort. Meanwhile, back in 2019, the Washington Post reported that overall revenue had been falling since 2015. As of 2021, the Trump Organization had borrowed around $125 million (£102m) on the property, according to The Independent—loans which Donald Trump himself is said to have guaranteed. 

What's more, when the pandemic struck, the resort reportedly laid off 560 workers. Change may be on the cards though, as new expansion plans could offer the resort a lifeline. In January 2022, Donald Trump announced that there would be 2,300 new luxury homes built at the Doral estate, as well as retail and commercial spaces, branding the move "perhaps the most exciting development in the country". 

In 2016, a $250 million (£205m) renovation of the Trump National Doral Golf Club was unveiled by Ivanka Trump. The luxurious Miami resort is now home to 643 guest rooms and over 100,000 square feet of space for business meetings and events. There's also a state-of-the-art clubhouse, numerous restaurants and lounges, plus a 50,000-square-foot spa, tennis courts and golf facilities.  

Clearly a busy man in 2012, Donald Trump also snapped up this 350-acre estate in Jupiter, Florida for a reported $5 million (£4.1m). Formally known as the Ritz-Carlton Golf Club & Spa, it was rebranded the Trump National Golf Club Jupiter, with the complex featuring a stunning golf course by award-winning designer Jack Nicklaus. A favourite among the Trump clan, Eric Trump, Donald's son, even owns a house on the property with his wife Lara.

The 65,000-square-foot clubhouse is ornately decorated, with coffered ceilings, dark wood beams, and gilded finishes throughout. There are six dining venues at the property, as well as a host of luxurious amenities, including a spa, a fitness centre, a resort-style pool, two hot tubs and cabanas. For overnight stays, there are four 800-square-foot guest villas and a 1,777-square-foot guest suite on offer. 

There's no shortage of plush entertaining spaces too. While it's regularly used for weddings, the Crystal Ballroom is pictured here back in March 2016, when Donald Trump hosted a press conference in the space during his run for the presidency. The space measures 10,000 square feet and features glittering crystal chandeliers, as well as striking views over the state-of-the-art golf course.

Yet another real estate investment in 2012, the Trump Organization was awarded the lease to Washington, DC's Old Post Office building by the General Services Administration, a branch of the US government. In 2014, an ambitious $200 million (£164m) redevelopment project began to transform the structure into the 263-room Trump International Hotel Washington, DC. Trump reportedly received millions of dollars from foreign governments to fund the construction. 

The hotel opened in October 2016, when Donald Trump was the Republican nominee for president, and a month before he was elected the 45th President of the United States. While Trump relinquished control of his companies when he assumed office, his assets were moved to a trust overseen by his sons, allowing him to still benefit from the federally-owned building. Unsurprisingly, there were calls for him to sell the property, which was labelled a magnet for "foreign businesses seeking favor" by critics. 

The Trump Organization eventually offloaded the hotel in 2022 for an eye-watering $375 million (£307m) and it's since been rebranded as a Waldorf Astoria. However, the quirks of Trump's premier hotel won't be forgotten quickly. Establishing itself as a high-society hub, the hotel's Benjamin Bar served rare wines in crystalline spoons for the hefty sum of $140 (£115). It's also said to have the largest ballroom in Washington, DC, which you can see here in this photo from the grand opening ceremony of the hotel. 

However, the hotel's pièce de résistance was the Trump Townhouse, which was dubbed the “largest Presidential Suite in Washington, DC,” on the hotel's website at the time. The executive space spanned 6,300 square feet and included two plush bedrooms, a 20-person dining room, a private gym and a self-contained entrance. On 9 November 2016, the night Trump was elected president, the suite was reportedly available to rent out for a staggering $33,434 (£27.5k) including tax. 

Loved this? Take an in-depth look at more of Donald Trump's homes