Donald Trump's 15 largest legal payouts, ranked

The former president's payouts to dodge prison

Donald Trump has been embroiled in thousands of court battles over the years, both as plaintiff and defendant. Not only is the 45th POTUS notoriously litigious, willing to sue any person or organisation that crosses him – he's a walking, talking lawsuit magnet who's faced accusations of sexual assault, fraud, and other serious crimes. 

Perhaps unsurprisingly, financial penalties and payouts to avoid court have seen Trump part with millions of dollars. Read on for our round-up of his biggest disclosed legal payouts. 

All dollar amounts in US dollars, and all monetary values adjusted for inflation. 

Contempt of court payout, 2022: $114,000 (£91k)

Exasperated by Trump's failure to comply with a court-issued subpoena for missing documents, New York judge Arthur Engoron showed how expensive it can be when you refuse to cooperate with the law by fining the former president a hefty $10,000 (£8k) a day for contempt of court. The clock began ticking on 25 April 2022.

Contempt of court payout, 2022: $114,000 (£91k)

Judge Engoron finally stopped the fine from accruing on 6 May 2022 and agreed to lift the contempt order on 11 May, as long as Trump complied with various stipulations concerning the handing over of the missing documents requested by New York Attorney General Letitia James (pictured) and paid the fines, which by that point totalled $110,000 (£88k). That's equivalent to $114,000 (£91k) today.

Scotland payout, 2019: $334,000 (£267k)

The majority of Trump's legal settlements are subject to non-disclosure agreements (NDAs) with the terms kept strictly under wraps, so there's no way of knowing exactly how much the former POTUS has paid out over the years.

Among the settlements that have been made public is the £225,000 ($282k) Trump was ordered to pay the government of Scotland in 2019.

Scotland payout, 2019: $334,000 (£267k)

The payout, which translates to about $334,000 (£267k) in 2023, was the final chapter in a long-running legal saga that saw Trump's golf company sue the Scottish government over plans to build a wind farm near the real estate mogul's Balmedie golf course.

The case was actually dismissed in 2015 by the UK's Supreme Court, but it took a lengthy four years for the court to finalise the settlement terms. 

The Paint Spot payout, 2017: $390,000 (£311k)

Staying with Trump's golf empire, his National Doral Miami course was dragged through the courts for three years by tenacious local paint store owner Juan Carlos Enriquez for failing to pay a bill of $32,536 (£26k), the last instalment of a $142,000 (£114k) contract. In 2014, Enriquez filed a lien for the money and attempted to settle.

The Paint Spot payout, 2017: $390,000 (£311k)

Trump's firm didn't budge, so The Paint Spot owner filed a lawsuit. The defence reportedly played hardball, but Enriquez refused to back down.

In 2016, a Miami-Dade Circuit Court judge ordered Trump National Doral Miami course to pay for the paint, and the following year an appeals' court ruled that Trump's company would have to cover Enrique's legal fees too, taking the payout to $315,586 (£252k), which is around $390,000 (£311k) today.

Illegal staff NDAs payout, 2023: $450,000 (£359k)

Legal bills have been coming in thick and fast for Trump in 2023. In February, the former POTUS's 2016 campaign settled a lawsuit filed in 2020 by then-presidential aide Jessica Denson. The ex-staffer argued she was a victim of sexual discrimination but was silenced by the Trump campaign and unable to take action due to the overly restrictive NDA she'd been forced to sign.

Illegal staff NDAs payout, 2023: $450,000 (£359k)

As it turned out, the NDA was illegal under the New York City Human Rights Law. With the case on Denson's side, the Trump campaign reached a settlement, which invalidated all the other NDAs its employees were made to sign in 2016.

The campaign bent over backwards to keep the terms of the settlement secret, but a court file revealed a figure of $450,000 (£359k), including $25,000 (£20k) personal compensation for Denson.

Washington DC payout, 2022: $777,000 (£622k)

In 2020, the government of Washington DC launched a lawsuit against Trump's Presidential Inaugural Committee, alleging it had misused non-profit funds by overpaying for events at the 45th POTUS's flagship hotel in the nation's capital, which had the end result of lining the pockets of Trump and his family.

Washington DC payout, 2022: $777,000 (£622k)

Trump, who as we've mentioned has bragged he'd never settle a lawsuit, did just that last year and agreed to pay out $750,000 (£601k), which is about $777,000 (£622k) in today's dollars. The money was then used to benefit three non-profit organisations.

Trump went on to slam DC Attorney General Karl Racine (pictured), calling the case "a further leg of the greatest Witch-Hunt in political history".

'Frivolous' Hillary Clinton case payout, 2023: $937,989 (£751k)

Trump's lawsuit accusing Hillary Clinton and others of racketeering and conspiring against him in the 2016 presidential campaign backfired big-time. The case came to a dramatic finale earlier this year when the former president and one of his lawyers were ordered to pay almost a million dollars in penalties.

'Frivolous' Hillary Clinton case payout, 2023: $937,989 (£751k)

In a ruling described as "scathing" by The Guardian, Donald Middlebrooks – the judge presiding over the case – reprimanded Trump and his attorney Alina Habba (pictured) for pursuing "the completely frivolous lawsuit", which was "brought in bad faith for an improper purpose".

Trump was also scolded for "repeatedly using the courts to seek revenge on political adversaries".

Omarosa payout, 2022: $1.4 million (£1.1m)

Trump's Apprentice protégée and former aide Omarosa Manigault Newman turned out to be his worst nightmare when she went rogue after her firing from the White House in 2017. The following year, the reality TV villain poured vitriol on Trump with her damning Unhinged exposé. To add insult to injury, the book launch was preceded by the release of the first of 200 secret tapes Newman had recorded while working at the White House.

Omarosa payout, 2022: $1.4 million (£1.1m)

Trump responded by calling Newman "a dog" and suing her for violating an NDA she'd signed. But it was the ex-White House staffer who had the last laugh.

In September 2021, Trump lost what Newman described as a "David and Goliath" case, and last year the court demanded his campaign stump up $1.3 million (£1.1m) – which works out at almost $1.4 million (£1.1m) in 2023 – to cover the defendant's legal fees.

Trump Parc East tenants payout, 1986: $1.5 million (£1.2m)

Trump bought 100 Central Park South in 1981 and planned to raze the 14-storey residential building he named Trump Parc East and build far more profitable upscale condos in its place. There was just one catch, or several to be precise: the tenants paying peanuts for the building's roomy rent-controlled apartments. After they refused to vacate their cherished properties, Trump allegedly turned nasty.

Trump Parc East tenants payout, 1986: $1.5 million (£1.2m)

Trump placed newspaper ads offering to shelter New York's homeless in the building and is said to have cut the heat and hot water, mentally tortured an elderly lady with terminal cancer by having holes drilled in her ceiling, and tried other dirty tricks to get the tenants to leave.

They fought back hard, however, and managed to stay. And in 1986, after spending more than a million dollars battling the residents, Trump agreed to pay their lawyers $550,000 (£440k), which is $1.5 million (£1.2m) today, and monitor the maintenance of the building. 

Tax fraud payout, 2023: $1.6 million (£1.3m)

In January this year, two Trump Organization subsidiaries were slapped with the highest-possible fines under New York law for operating a scheme offering top execs out-of-the-book perks to evade taxes. Shockingly, the offshoots were found guilty of a total of 17 felony crimes, with the Trump Organization's Chief Financial Officer Allen Weisselberg (pictured) convicted of grand larceny, criminal tax fraud, conspiracy, and other crimes.

Tax fraud payout, 2023: $1.6 million (£1.3m)

Weisselberg, who according to prosecutors illegally received $1.7 million (£1.4m) that he allegedly splurged on luxuries, was sentenced to five months at New York's tough Rikers Island jail.

The Trump Organization on the other hand was ordered by the New York court to pay $1.6 million (£1.3m). Predictably, the ex-POTUS denounced the case as a "witch hunt" and is supposedly appealing the verdict.

Antitrust payout, 1988: $1.9 million (£1.5m)

Back in the late 1980s, Trump was entangled in an antitrust case that hinged on whether he broke the law by failing to inform the relevant authorities about two massive stock purchases he'd made in 1986, both of which exceeded the reporting threshold of $15 million (£12m). Trump was attempting to take over slot machine company Bally Manufacturing and the parent of Holiday Inn, with the debacle incidentally resulting in the loss of thousands of jobs.

Antitrust payout, 1988: $1.9 million (£1.5m)

The sloppy takeover bids failed, and when the dust had settled the Federal Trade Commission (FTC) embarked on the antitrust suit against Trump.

In 1988, Trump agreed to settle the case for $750,000 (£601k), which equates to about $1.9 million (£1.5m) today – but he denied any wrongdoing and said he paid up only "to avoid protracted litigation".

Fraudulent foundation payout: $2.4 million (£1.9m)

In 2019, Trump was ordered to forgo $2 million (£1.6m) after New York judge Saliann Scarpulla ruled the then-president and his family misused funds from the tax-exempt Donald J Trump Foundation.

Exposed as a bogus charitable organisation, the foundation was, according to New York Attorney General Letitia James, "little more than a chequebook to serve Mr Trump’s business and political interests".

Fraudulent foundation payout: $2.4 million (£1.9m)

Trump admitted to dipping into the foundation's coffers to pay for a $10,000 (£8k) portrait of himself (pictured) by Miami-based artist Havi Schanz, $11,525 (£9.2k) worth of sports memorabilia and champagne, and other luxuries.

To settle the lawsuit, Judge Scarpulla ordered Trump to donate the penalty of $2 million (£1.6m), which is $2.4 million (£1.9m) today, to a group of non-profit organisations.

Undocumented workers payout, 1998: $2.6 million (£2.1m)

In 1980 Trump, desperate to complete the demolition of Manhattan's Bonwit Teller department store to make way for his flagship Trump Tower, hired a group of undocumented Polish construction workers who it's been alleged "put in 12-hour shifts with inadequate safety equipment at subpar wages that their contractor paid sporadically, if at all".

Undocumented workers payout, 1998: $2.6 million (£2.1m)

The disgruntled labourers got together in 1983 and filed a class-action lawsuit in an effort to get Trump to pay them compensation and contribute to a union benefits fund.

The case dragged on and on, finally coming to an end in 1998 when Trump, who insisted he knew nothing about the poor working conditions on the site, agreed to pay $1.4 million (£1.1m). Around a third of the total, which equates to $2.6 million (£2.1m) today, went towards pensions for the workers.

E Jean Carroll sexual assault payout, 2023: $5 million (£4m)

After a two-week trial that ended on 9 May this year, a jury in a New York civil court found Trump liable for sexually abusing former Elle magazine columnist E Jean Carroll (pictured) in a dressing room in Manhattan's Bergdorf Goodman department store in the mid-1990s. Carroll's claim that Trump raped her was rejected, but the writer's allegation that Trump later defamed her was upheld.

E Jean Carroll sexual assault payout, 2023: $5 million (£4m)

Trump, who is appealing the ruling, had publicly denied the incident ever happened, remarking that the writer wasn't his “type”, which spurred her on to fight him in the courts.

Incredibly, the defamation attracted a higher penalty, with the former POTUS ordered to pay Carroll $3 million (£2.4m) for damaging her reputation and $2 million (£1.6m) for the sexual abuse.

Trump Taj Mahal anti money-laundering violation payouts, 1998 and 2015: $14 million (£11.3m)

Trump's now defunct Taj Mahal Casino in Atlantic City flouted money-laundering regulations numerous times.

In 1998, the venue was fined $477,000 (£383k), the equivalent of $1.2 million today (£965k), after the Treasury's Financial Crimes Enforcement Network (FinCEN) found it broke the rules 106 times during its first year and a half of operation in the early 1990s. 

Trump Taj Mahal anti money-laundering violation payouts, 1998 and 2015: $14 million (£11.3m)

Then in 2015, the Taj Mahal was fined again by FinCEN for "willful and repeated violations of the Bank Secrecy Act", but this time the bureau pulled out all the stops, issuing a monster $10 million (£8m) fine – the biggest ever levied by the US government against a casino.

The struggling venue, which had petitioned for bankruptcy the previous year, ended up closing down for good in 2016. 

Trump University scam payout, 2018: $30.2 million (£24.2m)

Described by former New York Attorney General Eric T. Schneiderman as a "sham university", Trump's ill-fated namesake educational institution, which operated from 2005 to 2010, was a seminar series and real estate training programme masquerading as a university that according to critics enticed students to pay up to $35,000 (£28k) to learn Trump's real estate investing secrets, but failed to deliver on its promises. 

Trump University scam payout, 2018: $30.2 million (£24.2m)

Following its closure, the faux university, which was completely unaccredited and didn't offer any meaningful qualifications, became the subject of a lawsuit filed by the New York Attorney General's office, as well as two class-action lawsuits. Trump vowed to fight tooth and nail to win, but settled all three cases in 2016 for a whopping $25 million (£20m), which translates to $30.2 million (£24.2m) in 2023. 

Now uncover the many lawsuits that Donald Trump is still battling today