‘Shameless venality’: how a flurry of lawsuits has thwarted Trump’s self-enrichment schemes

Courts have issued stinging rebukes to president’s ‘blatant’ financial ploys as pro-democracy groups defend ‘government of laws, not of men’ pillar

Donald Trump’s legal and political ploys to increase his wealth and boost Republican electoral prospects have fueled lawsuits by non-partisan groups, prompting federal judges to issue stinging rejections to some of the president’s schemes.

Several lawsuits were filed in 2026 against Trump’s schemes to benefit his bottom line by reducing potential tax liabilities, boosting his Truth Social platform financially by offering big investors early access to his posts, and helping Republicans by using federal funds to pay for highly partisan ads touting Trump’s record in the run-up to the midterm elections, in which Republicans suffered a heavy defeat.

The major lawsuits against Trump’s financial ploys have been the handiwork of several nonpartisan groups including Democracy Defenders Fund and the Campaign Legal Center.

In response, judges in Florida and New York used strong language to condemn and help nullify some of Trump’s financial stratagems. Florida judge Kathleen Williams castigated a Trump scheme backed by the justice department to settle a $10bn lawsuit he filed against the Internal Revenue Service over an old leak of his tax information to the New York Times.

Williams ruled that the Trump backed deal to set up a $1.8bn slush fund to pay alleged victims of political persecutions under Joe Biden and giving him immunity from IRS audits before May 2026 was “premised on deception” and a “fraud against the court”.

In a separate legal blow to Trump in the closing weeks of the campaign, the president was rebuked by a federal judge in New York, for channeling $20m of public funds to run ads touting his administration’s achievements. The ads were widely attacked as campaign ads and propaganda.

Former judges and ex-DoJ lawyers say that he Trump moves to boost his bottom line and political drives with backing from DoJ lawyers exemplify various kinds of Trump “corruption”.

Stacey Young, a former DoJ lawyer who set up Justice Connection last year as a network to defend the justice department workforce and the rule of law, told the Guardian: “The justice department’s leadership believes it has one chief client: President Trump. They have allowed him to use the department to protect his financial interests, punish his enemies, and reward his friends.

“Thanks to the efforts of some of the country’s best litigators, the people of the United States are pushing back and standing up for the ideal that we remain a government of laws, not of men.”

Further, retired federal appeals court judge J Michael Luttig said: “The courts have recently begun to strike down Trump’s countless schemes of blatant and shameless venality and corruption in the forms of self-enrichment, bribery, and extortion. That is the through-line of these three cases and the numerous other cases to come.”

For Luttig, the court rebuffs are part of a broader trend of federal courts also rejecting as unconstitutional major presidential initiatives including tariffs and birthright citizenship.

Luttig’s analysis was underscored by a July lawsuit filed by Democracy Defenders Fund and a coalition of 35 ex-judges, including Luttig, to kill a key piece of Trump’s proposed settlement of his $10bn lawsuit against the IRS by establishing a $1.8bn fund to pay alleged victims of political persecution that could have helped some January 6 Capitol rioters.

The DoJ dropped the slush-fund idea after Williams ruling and some political blowback by Congress. But despite Williams’s legal objections and sharp criticism from Democratic senators, including Elizabeth Warren of Massachusetts, a provision is still in effect providing immunity to Trump, his family and the Trump Organization from investigations and prosecutions of past tax matters by the IRS as compensation over a leak of his tax returns.

In her ruling, Williams charged that the plaintiffs initiated the lawsuit “for an improper purpose – to gain the imprimatur of judicial legitimacy for a ‘settlement’ that had no viable basis in law or fact”.

Williams’s scathing opinion in mid-July noted that Trump was on both sides of the issue and that the court itself was perhaps “the victim of fraud”. Williams concluded that the plaintiffs had acted in bad faith by “collusively filing a lawsuit with claims subject to multiple dispositive defenses solely to provide cover for a collusive settlement”.

Citing language from an earlier ruling, Williams said “this case is part of Mr Trump’s pattern of misusing the courts to serve political purposes”. In summary, Williams wrote, acidly, that the plaintiffs “pursued this lawsuit in bad faith for the improper purpose of dishonestly advancing a political narrative”.

Trump’s lawyers in late July said they would appeal the Williams order. In late September, a federal appeals court for the 11th circuit rejected a request from Trump and his lawyers to immediately lift sanctions that Williams imposed in response to the settlement Trump and the DoJ backed over the leak of his tax returns.

In its ruling, the appeals court denied a request by two Trump lawyers, Alejandro Brito and Daniel Epstein, to pause sanctions against them over their handling of his $10bn lawsuit against the IRS. The court ruled the lawyers had not demonstrated they would succeed in challenging finding that they acted in bad faith.

In another legal blow for Trump, two restraining orders were issued in October by district judge Jennifer Rochon in New York to stop his use of public funds for financing campaign style ads after Campaign Legal Center Action representing Common Cause, along with Public Integrity Project Action and Democracy Forward sued.

In her second emergency order on 30 October, Judge Rochon ruled that three ads could no longer run using government funds on Instagram and two other sites since they were “purely partisan” .

One of the ads echoed Trump’s dubious claim that if Republicans maintained control of Congress, all Americans would receive $5,000. The three ads Rochon ordered removed were headlined “$5,000 to Americans” the “Cost of Socialism” and “Every Democrat Voted against No Tax on Tips”.

Shortly before Rochon’s first ruling, Trump in a Truth Social post on 5 October defended using government funds for the ads and blithely stated that tapping public funds was “rather standard”.

But with growing criticism, including from some Republicans, Trump announced he would pay for them himself from his political fundraising operation. The justice department also tried to forestall the first restraining order by asserting that “the alleged offending conduct will end tomorrow”.

Renata O’Donnell, a senior legal counsel with Campaign Legal Center who worked on the case, told the Guardian: “The Department of Homeland Security used $20m in taxpayer dollars to pay a private ad agency for airtime for government-created propaganda. This is blatantly illegal.”

O’Donnell added: “In direct violation of the law, White House staff, whose salaries are paid with taxpayer dollars, were creating propaganda, including ads that promised people $5,000 to vote Republican.”

In another pending legal battle that courts have yet to rule on, Democracy Defenders Fund filed a lawsuit with the San Francisco city attorney, the Washington Litigation Group and Platkin LLP to block a Trump financial gambit to offer special early access to his Truth Social posts to users who pay a fee as high as $100,000 per month to the parent company of Truth Social.

The lawsuit was filed in mid-September against Trump Media and Technology Group, which operates and owns Truth Social.

San Francisco city attorney David Chiu asked the San Francisco superior court to bar Trump Media from offering its new service, dubbed “Trump API”, or a similar one, plus provide monetary damages for violating the public trust and the state’s unfair competition law.

“Trump Media created a marketplace that enables insider trading, which Trump directly profits from,” Chiu said in a statement. “This scheme turns the public trust into private profit. It is corruption, plain and simple.”

A Trump Media spokesperson ridiculed the lawsuit when it was filed, charging that “the people of California should outsource their future lawsuits to AI chatbots who, unlike the leftwing activists masquerading as attorneys who filed this lawsuit, will grasp the basic distinction between public and nonpublic information”.

David Ogden, a senior counsel with DDF who has worked on the case, noted that “Congress made clear that the president, like any public servant, shouldn’t be permitted to profiteer off of special access to government information. It’s a violation of the public trust and it’s important that it be stopped.”

In the eyes of Barbara McQuade, former US attorney for eastern Michigan, who now teaches law at the University of Michigan, the different court rulings against Trump’s financial ploys reveal his penchant for “personal enrichment” and political ploys during his presidency.

“It seems that Trump has no shame about using his office for personal enrichment. We can’t count on his own conscience, ethics or advisers to check his worst instincts, but the courts have seen through his various schemes, from his slush fund to his use of taxpayer funds for political ads.”