Massive Insider Trading Can't Be Ruled Out of Trump's Carnival of Grift: An Executive Watch Roundup
Our late-May selection of the president's latest and greatest assaults on the rule of law
The Institute for the Study for Modern Authoritarianism (ISMA), the parent organization of The UnPopulist, launched Executive Watch early in Trump’s second term. It has been meticulously documenting this White House’s illicit actions since then.
Below is our biweekly selection of new entries. Bookmark this page, which contains a chronological scroll of the abuses. And also this post, which sorts and lists them under our 5 “P” categories:
After reading the following entries, tell us: Which of these abuses is the most troubling, and why?
May 22, 2026
Trump’s Election-Security Czar Is Reupping Debunked Conspiracy Theories to Ban Dominion Voting Machines in an Effort to Subvert Elections
Category: Power Consolidation
Kurt Olsen, Trump’s election-security czar, tried to ban voting machines used in more than half of U.S. states—relying on the same debunked conspiracy theories about Dominion Voting Systems that Trump has peddled since 2020.
Reuters explains via U.S. News & World Report:
White House adviser Kurt Olsen, a lawyer Trump has tasked with proving widely debunked election-rigging conspiracy theories, pushed the plan to target Dominion Voting Systems machines. The idea emerged as Olsen and other officials brainstormed about how the federal government could take control over elections from U.S. states. Olsen wanted a national system of hand-counted paper ballots—a demand election-security experts say would be less accurate and potentially riskier than the current system. The plan got far enough that in September, Commerce Department officials began exploring what grounds could be invoked to execute it.
A main focus of Olsen’s efforts: the debunked theory that Dominion machines were infected with code controlled by Venezuelans to steal the 2020 election from Trump. Repeated investigations and lawsuits since 2020 have produced no evidence Dominion machines were hacked. In 2023, Fox News paid Dominion $787 million in a defamation case over false election-rigging claims. Olsen aimed to invalidate the machines before the midterms. …
The episode is part of a far-reaching Trump administration push to encroach on state and local governments’ authority to run elections—which is granted to them in the U.S. Constitution to prevent the executive branch from seizing power.
This fits within a broader pattern of Trump efforts to interfere in elections, including executive orders threatening states, working to push through the SAVE Act, and trying to seize election records.
As Andy Craig has argued for The UnPopulist, America’s election system is robust enough to withstand a fair amount of meddling. But even if it is relatively unlikely that Trump will fully succeed in his efforts to subvert American elections, his dangerous intentions are clear enough.
May 21, 2026
DHS Issues a Nationwide Alert Against a Comedian for Making a Parody ICE Snitch Site
Category: Power Consolidation
The Department of Homeland Security has issued a “Be on the Lookout” (BOLO) alert—normally reserved for major suspects and threats—to law enforcement agencies across the country. The alert target is Ben Palmer, a comedian from Nashville who created a parody website mocking ICE’s tip submission system, which is a glorified snitch line.
The Guardian has the details:
The Bolo was issued by the DHS’s Nashville field office in February, about a week before the Washington Post profiled Palmer. While Palmer’s site uses language such as “official report form,” the comedian doesn’t claim to work for ICE and the privacy policy contains a disclaimer that the site is “for parody.” … In an email, a DHS spokesperson said: “There is no ‘investigation’ into this individual—this document is an internal memo shared for awareness purposes only.” …
Darius Reeves, a retired ICE field office director, said Bolos more commonly include terms such as “‘considered armed and dangerous,’ ‘approach with caution’ or ‘do not approach at all.’” He said a Bolo being issued for a comedian was “unusual.” …
Palmer isn’t the first comedian targeted by the DHS under the Trump administration for satirizing immigration enforcement. Earlier this year, federal officers took down and detained Rob Potylo while he was wearing a giraffe costume and demonstrating against ICE in Minneapolis. In 2018, DHS agents showed up at the Brooklyn home of comedian Jake Flores after he posted satirical tweets about ICE.
The First Amendment provides satirists and prank artists with significant protections, making a nationwide federal law enforcement alert an extraordinary response to what is likely constitutionally allowed political speech. (Our correspondent, Jacob Grier, who protested ICE as an inflatable dachshund has, so far at least, avoided provoking a BOLO of his own!)
The government has a legitimate interest in ensuring the integrity of its reporting systems—and Palmer’s site did fool many callers who genuinely believed they were tipping off ICE. But being fooled while trying to report your neighbor to immigration authorities is a different kind of harm than the disruption of a federal law enforcement process, and DHS’s own alert acknowledged no investigation was underway. That makes the widely circulated bulletin look less like a public safety measure and more like an attempt to track a vocal critic.
May 21, 2026
Trump Threatens New Military Action, This Time Against Cuba
Category: Policy Illegality
Despite his war of choice in Iran going none too well, Trump is shifting his sights to another military conquest, this time closer to home: Cuba. His administration has indicted former Cuban President Raúl Castro and imposed an oil blockade. Now Trump is saying he may have “the honor of taking Cuba.”
CNN provides the details:
The Cuba gambit is the latest test of the administration’s strategy of ratcheting up economic duress by imposing a blockade while raising the prospect of the use of force to get enemies to capitulate. This worked in Venezuela—but Venezuelans are yet to see their hopes for democracy made good. A similar approach has been such a failure in Iran that Trump may have no option but to restart the war. Meanwhile, UN experts warned that the US oil blockade was threatening “fuel indispensable for electricity generation, water and sanitation systems, hospitals, public transportation, and food production.”
We’ve heard this story before: in Venezuela, where the Trump administration merely replaced one corrupt leader with another—Delcy Rodríguez, Maduro’s former vice president—and in Iran, where Trump falsely promised to bring freedom to Iranians protesting their regime. Trump cares nothing for the people of other countries and is not interested in helping them. What he does want is to start illegal wars to reinforce his image and try to bolster his flagging popularity. As Democratic Sen. Ruben Gallego put it: “The American people are not asking for another war. They want us focused on building housing in Arizona—not bombing housing in Havana.”
May 21, 2026
Trump Demands Republicans Fire the Senate Parliamentarian After She Blocked His Ballroom and Also Scrap the Filibuster
Category: Power Consolidation
Elizabeth MacDonough, the Senate Parliamentarian, ruled on May 16 that the Senate reconciliation bill cannot, as currently written, be used to fund Trump’s ballroom. In response, Trump issued a deranged Truth Social post calling on Senate Republicans to fire the Parliamentarian (and eliminate the filibuster) or else find themselves “looking for a job much sooner than you thought possible.”
Time has the story:
“Shockingly, Republicans have kept the very important position of ’Parliamentarian’ in the hands of a woman, Elizabeth MacDonough, who was appointed, long ago, by Barack Hussein Obama and a vicious Lunatic known as Senator Harry Reid, who ran the Senate for the Dumocrats with an iron fist,” Trump wrote on Truth Social. “Over the years, she has been brutal to Republicans, but not so to the Dumocrats—So why has she not been replaced? … Get smart and tough Republicans, or you’ll all be looking for a job much sooner than you thought possible!” …
MacDonough over the weekend ruled security funding for Trump’s new White House ballroom did not meet the strict guidelines governing what Republicans can include in the budget reconciliation package they are trying to pass. The proposal to allocate $1 billion in security additions for the White House and ballroom violated the Byrd Rule, she determined, as it was too broad to be included in the bill, which cannot be filibustered.
As with many of his tantrums, Trump is once again taking aim at the very idea of procedural checks on his authority and the bedrock principle that the other branches of government don’t simply exist to rubberstamp his pet projects but to check his unhinged designs. (This is the same ballroom that MAGA world tried to make happen by exploiting a shooting at the White House Correspondents’ dinner, with a seemingly coordinated campaign of influencers and lawmakers insisting the attack proved the ballroom was a national security necessity.)
May 20, 2026
Trump Settles His Own Lawsuit Against His Own IRS by Creating a $1.776 Billion Slush Fund for Political Allies and Blanket Immunity for Himself and His Family
Category: Personal Grift
Earlier this year, Donald Trump sued the IRS and Treasury Department over the actions of a former IRS contractor, who illegally disclosed Trump’s tax returns that, unlike previous presidents, he refused to release voluntarily. Despite serious weaknesses in the case—including the fact that it was filed after the statute of limitations, and similarly situated plaintiffs received only a formal apology, not money—the Justice Department settled with Trump on behalf of the government by creating a $1.776 billion “Anti-Weaponization Fund” that could be used to compensate Jan. 6 defendants prosecuted under the Biden administration. It purports to grant Trump and his family broad immunity from a wide range of government actions against them.
As if that were not bad enough, the fund will have no independent oversight and no disclosure requirements. Lawfare reports:
The fund—drawn entirely from the federal Judgment Fund, a permanent congressional appropriation used to pay court settlements against the United States—will be used to dispense taxpayer money to people who suffered from purported Democratic “weaponization” and “lawfare.” While Trump is not expected to receive compensation from the fund himself, money will be doled out by a five-member board he effectively controls, operating under procedures that need not be disclosed, with the identities of recipients potentially kept secret. …
By waiving any matter that “could be pending” before any agency or department, the agreement purports to give the Trump family blanket immunity from the government for everything they have done. The parenthetical “(including tax returns filed before the Effective Date)” is at once logically unnecessary, possibly illegal, and clarifying. According to a 2024 New York Times report, an ongoing IRS audit might cost Trump over $100 million. It stands to reason that this is what the language was designed to address.
This self-dealing scheme exploited loopholes in the legal system in such a manner that it’ll be hard to use the law to stop it, although some police officers who were injured on Jan. 6 have sued.
Judge Kathleen Williams, who was handling Trump’s lawsuit, was seeking external advice on whether Trump could sue his own government. She was scheduled to be briefed on May 20, but the Justice Department hastily settled with Trump two days prior. Since the settlement is outside her jurisdiction, she cannot rule on the legality of the slush fund. Even by this administration’s standards, this is brazen. Check out Walter Olson’s piece for The UnPopulist on the new low that this administration has set.
May 20, 2026
A Panel Packed With Trump Loyalists Rubberstamps His Plans to Build ‘Arc de Trump’ Without Congressional Approval
Category: Power Consolidation
The U.S. Commission of Fine Arts—packed with the president’s allies after Trump fired all of the previous members—has approved plans for a 250-foot-tall triumphal arch opposite the Arlington Memorial Bridge, in Washington, D.C. Survey teams are already on the site even though Congress has yet to approve Trump’s latest vanity project. The administration bizarrely claims it does not need this approval.
The Washington Post explains:
[A]dministration officials have cited a 1924 report by a federal commission charged with designing the Arlington Memorial Bridge. That report called for building a pair of 166-foot-tall columns, surmounted by statues, on Columbia Island that would frame the nearby Lincoln Memorial. Congress formally ratified the commission’s report in 1925, and the Memorial Bridge was soon built. However, the columns were not constructed, and Trump officials today argue that in building the arch they would be carrying out past lawmakers’ wishes. …
“The notion Congress a century ago authorized construction of this 250-foot arch in Memorial Circle is absurd,” said Wendy Liu, a lawyer at Public Citizen Litigation Group. “This is their playbook,” said Rep. Jared Huffman (D-California). “The fact that they’re trotting out this tortured argument that a 100-year-old authorization for something totally different satisfies a law today is laughable, but consistent with their pattern of ignoring Congress.”
There is no law too old or obscure that our Dear Leader won’t dig out and torture to satisfy his vanity.
May 18, 2026
Pete Hegseth Campaigns Against Sitting Republican Congressman in Possible Hatch Act Violation
Category: Power Consolidation
Pete Hegseth, Donald Trump’s secretary of defense, personally campaigned against sitting congressman Thomas Massie in the Kentucky Republican primary—an unprecedented deviation from past Pentagon norms. (Massie, who became that rare thing in the Trump era, a Republican who is at least sometimes willing to oppose the president on principle, has since been defeated.)
Hegseth’s appearance raised immediate questions about a potential Hatch Act violation, the law that prohibits executive branch officials from using their official positions to influence elections. The defense secretary’s team preemptively tried to deflect these questions by insisting he would be there “in his personal capacity.”
The Hill gives us the story:
Hegseth will … be in Kentucky on Monday as part of official duties to award Purple Heart medals to 101st Airborne Division soldiers and to administer the oath of enlistment to 190 re-enlistees at Fort Campbell. He will then attend a rally for Gallrein put on by conservative advocacy organization America First Works. … “I can’t remember a secretary of defense coming to a political event like this,” said Tres Watson, a former spokesperson for the Republican Party of Kentucky, adding that he had “significant questions about the legality or appropriateness.” Watson said it was “fairly certain” to be a Hatch Act violation. …
“I’m proud here to stand with Ed Gallrein,” Hegseth said at the event. “President Trump does not need more people in Washington who are trying to make a point, especially from his own party. He needs people trying to help him win, to vote with him when it matters most.”
The Hatch Act exists precisely to prevent the executive branch from using official power and resources to influence elections. The claim that Hegseth was there “in his personal capacity” does not withstand scrutiny: he arrived on official Pentagon travel, in his capacity as a Cabinet secretary, before attending a transparently partisan rally the same day. The message to every Republican member of Congress was unmistakable: if you cross this administration, the full apparatus of the executive branch, including its senior-most military leadership, will be deployed against you, laws and norms banning such abuse of the state machinery be damned.
May 14, 2026
Trump Routinely Buys Stock in Companies Days Before His Administration Approves Lucrative Decisions for Them
Category: Personal Grift
Donald Trump purchased stock in Nvidia and AMD just days before his own administration approved lucrative chip deals that sent both companies’ valuations soaring. The purchases are among 3,642 securities transactions—roughly 58 trades per trading day—that Trump disclosed in a 113-page filing covering January through March 2026, representing between $220 million and $750 million in total activity.
NOTUS reports:
Trump purchased $500,000 to $1 million worth of Nvidia stock on Jan. 6, a week before the Commerce Department officially approved the sale of some Nvidia chips to China. … Trump purchased $1 million to $5 million dollars worth of Nvidia stock on Feb. 10, only a week before Nvidia announced a major computer processing power deal with AI and social media giant Meta. …
AMD, another AI semiconductor company, was also authorized by the Department of Commerce to sell their chips to Chinese customers on Jan. 13. Trump purchased $50,000 to $100,000 worth of AMD stock on Jan. 6. …
Trump purchased at least $260,000 worth of Palantir stock during the first three months of 2026. … In February, Palantir struck a billion-dollar agreement with the Department of Homeland Security to use the company’s software in the president’s deportation surge. …
On Feb. 10, Trump also purchased $1 million to $5 million in shares of Axon, the company that makes Tasers. … Immigration and Customs Enforcement outlined its plan to spend $220 million on Tasers over five years on Feb. 24 … in what would be a major boon for Axon.
The White House says Trump’s assets are held in a trust managed by his children with no input from him, and that “there are no conflicts of interest.” The disclosure forms do not specify who placed the trades. What the forms do establish is that the president of the United States holds between $1 million and $5 million in Nvidia stock while his Commerce Department shapes the regulatory environment that determines Nvidia’s access to the Chinese market.
The disclosure was also filed late—a handwritten notation on the cover confirms Trump paid late-filing fees. A president trading at this volume, in companies his administration regulates, while missing his own disclosure deadlines, shows total contempt for the ethical rules meant to constrain exactly this kind of behavior.
At his own State of the Union, Trump called on Congress to ensure members “cannot corruptly profit from using insider information.” Democratic Rep. Mark Takano shouted back: “How about you first?”
May 14, 2026
DOJ Drops Federal Fraud Charges Against Indian Billionaire After He Hires Trump’s Lawyer and Pledges $10 Billion Investment
Category: Political Corruption
Gautam Adani, one of the world’s wealthiest men, was indicted by federal prosecutors for orchestrating a massive $265 million bribery scheme to secure solar energy contracts, hiding the corruption from U.S. investors to raise capital. Following aggressive backchanneling after Trump’s return to office, the Justice Department moved to permanently dismiss the criminal indictment—with prejudice—just weeks after Adani’s legal team formally offered a $10 billion U.S. investment deal during private negotiations.
The New York Times has the details:
The reversal came after the Indian billionaire, Gautam Adani, hired a new legal team led by Robert J. Giuffra Jr., one of President Trump’s personal lawyers and the co-chairman of the prominent firm Sullivan & Cromwell. ... Mr. Giuffra ticked through about 100 slides outlining why prosecutors lacked basic evidence, as well as the jurisdiction even to bring the case, one of the people said. Another slide also made an unusual offer: If prosecutors dropped the charges, Mr. Adani would be willing to invest $10 billion in the American economy and create 15,000 jobs. ...
The proposal—which Mr. Trump could have held up as a political and economic win—underscores the highly transactional approach to justice in Mr. Trump’s second term. Over the past year, he has awarded pardons to his donors and even a business partner, while prosecutors in his Justice Department have dropped charges and investigations against other political allies. Those results, a striking break from prosecutorial norms, have fueled the perception that freedom is up for sale in Mr. Trump’s Washington, emboldening defendants to offer economic settlement terms that were once unthinkable.
The transaction is about as naked as pay-to-play corruption gets, but the operational mechanics elevate it to a historic level of audacity. Robert Giuffra simultaneously serves as both Donald Trump’s personal defense lawyer and Adani’s representative. In other words, the president’s own attorney used a slide presentation to pitch an economic quid pro quo to the president’s own Justice Department: a promise of corporate investment in exchange for permanently scrapping criminal fraud charges against a foreign billionaire.
May 13, 2026
Trump Guts the DOJ Unit That Investigates Public Corruption From 40 Attorneys to Just Two
Category: Power Consolidation
The Justice Department’s Public Integrity Section has operated for 50 years under both parties, investigating corruption by public officials at every level of government without regard to political affiliation. Under Trump, it has been reduced from 40 full-time attorneys to two.
NPR reports:
Legal experts say the pardons are but one way the Trump administration has undermined the fight against public corruption. ... Another piece is the dismantling of the Justice Department’s Public Integrity Section, which was created after Watergate to investigate and prosecute public corruption and election crimes.
Under this administration, the section has been decimated. It had around 40 full-time staff when Trump returned to office in January 2025. That number has dropped to just two full-time attorneys today, according to current and former officials. It was handling around 175-200 open matters ... when Trump returned to office. That number has plummeted to around 20 today, those officials say.
The gutting of the Public Integrity Section began with the Eric Adams episode; DOJ’s career attorneys resigned to protest the corrupt quid pro quo in which corruption charges were dropped against the former New York City mayor in exchange for his cooperation on immigration enforcement. The administration then suspended the requirement that corruption cases be reviewed by the Public Integrity Section at all, removing even the procedural check on partisan prosecution.
The result is an administration that has simultaneously eliminated the unit designed to hold it accountable while signaling to every public official in the country that corruption carries no consequence—provided you are on the right side.
© The UnPopulist, 2026
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An excellent roundup! What stands out the most to me is less any single scandal than the way institutional constraints are being systematically removed or neutralised. Insider trading, selective enforcement, and executive overreach all become far more consequential once internal accountability mechanisms are weakened or dismantled.
The Public Integrity Section cuts are especially significant in that respect. Once the capacity to investigate corruption inside the executive is reduced to near-nothing, the distinction between lawful governance and discretionary self-dealing becomes increasingly procedural rather than substantive.
Taken together, these entries read less like discrete abuses and more like stages in a broader shift: the state’s enforcement and oversight architecture being progressively retooled away from constraint and toward alignment with executive interest. Well-written and researched!
Which of these abuses is more cringe worthy?
They are all facets of a consistent plan to dismantle the guardrails that protect democracy in order to achieve and indefinitely keep power and wealth in the hands of a self appointed group.
But one matters more than the others and that is power consolidation, the tactic that allows all the others to become entrenched.
It is why Orban failed to stay in power and Putin still has not.
In America, the one lever that still works, given a captive Congress and a weakened Judicial branch, is the holding of free and fair elections.
And that makes it the main target of power consolidation efforts, which, if successful will allow all the other abuses to continue unchecked.