The Paper Trail: May 26, 2026

Trump Escapes $100M Tax Penalty;
The Front Groups Fueling the 2026 Midterms
The Ubiquity of Gambling in Televised Sports;
And More.

May 26, 2026

Top stories for May 26, 2026

The White House is ordering agencies to place its new app on all employees’ government phones: The White House recently unveiled a new app to give the public “unfiltered” access to “key priorities,” “historic moments,” and “policy breakthroughs.” Now, it’s directing agencies to install the app on the government phones of federal employees. Cybersecurity experts, who warned about vulnerabilities in the app soon after it debuted, say the move is “dangerous.” (Natalie Alms and Eric Katz, Government Executive)

The Trump administration pushed out nearly half of its nuclear waste cleanup team: Hundreds of federal workers in charge of nuclear waste cleanup took the administration’s resignation offers. The most radioactively contaminated parts of the country are now being overseen by a fraction of the staff. (Anna Kramer, NOTUS)

With Trump’s deal, a possible $100 million IRS penalty melts away: Last week’s agreement with the Justice and Treasury departments settling President Trump’s lawsuit against the IRS will wipe away a tax audit that Trump has been fighting since 2010. The agreement frees Trump from a potential adverse ruling that could have cost him more than $100 million. (Russ Buettner, New York Times)

Trump has been investing in companies and then pumping them in his speeches: The president has been a highly active stock trader in 2026, executing thousands of transactions in companies impacted by his administration’s policies and his public statements. (Judd Legum, Mother Jones)

Trump airport branding deal opens new route to profit for family: Last week, a Florida county commission voted to hand over trademark and commercial rights of the former Palm Beach international airport to President Trump. Analysts predict the president is likely to net millions from the unorthodox legal agreement. (Richard Luscombe, The Guardian)

Trump’s unofficial Venezuela viceroy shapes U.S. policy, raising oversight concerns: Mauricio Claver-Carone has no official job in the U.S. government, but he has an outsize role in determining the future of Venezuela. He has been instrumental in picking among aspiring investors in the country’s oil industry. (Samantha Schmid et al., Washington Post)

Who’s spending in your congressional election? We tracked the front groups fueling the 2026 midterms: Big money forces in politics are growing ever more sophisticated about exploiting legal loopholes to obscure their identity. Groups with innocuous-sounding names are setting up pop-up affiliates, gaming disclosure deadlines, and using conduits to hide the origins of their cash. (Matt Sledge, The Intercept)

Trump Anti-Weaponization Fund

Trump’s anti-weaponization fund gets its first applicant: Former Trump administration official Michael Caputo last week filed the first known claim under the DOJ’s new $1.8 billion “Anti-Weaponization Fund.” Caputo requested $2.7 million in restitution and reimbursement stemming from the FBI’s 2016 “Crossfire Hurricane” investigation into ties between the Russian government and Trump’s first presidential campaign. (Jenna Monnin, NOTUS)

Trump’s allies are already lining up to apply to his $1.8 billion fund: January 6 rioters, George Santos, and Rod Blagojevich are among the wide range of people eyeing the anti-weaponization fund. (Meryl Kornfield, Washington Post)

Two Jan. 6 police officers sue to block Trump DOJ’s “slush fund”: Former Capitol Police Officer Harry Dunn and former Metropolitan Police Officer Daniel Hodges, both of whom defended the Capitol on January 6, 2021, filed a lawsuit to block the fund, claiming that it emboldens violence against police and rewards sedition. (Steve Benen, MS NOW)

Iran War

Congressional report tallies 42 U.S. aircraft lost or damaged in Operation Epic Fury: A CRS report tallied 42 U.S. aircraft lost or damaged during Operation Epic Fury. It’s the most complete public accounting of a war the Pentagon has yet to assess on its own terms. (Michael Scanlon, Military Times)

Prediction Markets

House lawmakers launch insider trading probe into Kalshi and Polymarket: The House Oversight Committee is investigating Kalshi and Polymarket over alleged incidents of insider trading tied to the Iran war and to the capture of former Venezuelan leader Nicolás Maduro. (Mary Cunningham, CBS News)

Insurrection

DOJ says it scrubbed news releases about Jan. 6 criminal cases from its website: The DOJ acknowledged it removed press releases about criminal cases related to the insurrection, calling the information “partisan propaganda.” Among the releases removed from the site were those concerning seditious conspiracy cases against members of the Proud Boys and Oath Keepers. On Friday, federal prosecutors filed motions to formally dismiss those cases. (CBS News)

White House Ballroom

Trump reveals new details of bunker-like ballroom with drone base: To bolster his argument that Congress should allocate $1 billion to pay for its construction, President Trump told reporters last week that the White House ballroom would have a drone base on an “impenetrable steel” roof, titanium fencing, and a military hospital and research facilities as part of a six-story subterranean complex. (Steve Holland and Humeyra Pamuk, Military Times)

Defense and Veterans Affairs

Amid rising military suicides, services can’t tell if prevention training is effective: Despite a military suicide rate that has continued to climb since 2011, most military services don’t have accountability measures to ensure troops are taking required prevention training. And, according to the GAO, they don’t know if the training actually makes a difference. (Hope Hodge Seck, Military Times)

Business and Finance

How prediction markets and crypto firms steamrolled a watchdog agency: The Commodity Futures Trading Commission has been mowed down by the powerful business interests it’s supposed to oversee. In the past 16 months, the CFTC has shrunk its work force, purged career officials, sharply curtailed crypto enforcement, and helped out prediction markets at virtually every turn. (Sharon LaFraniere and David Yaffe-Bellany, New York Times)

We had AI analyze 50 hours of sports on TV. It detected gambling ads everywhere: The gambling industry, which was viewed by professional league owners and the NCAA as a grave threat a little over a decade ago, is now so integrated with televised sports that it’s virtually unavoidable. Analysis of 50 hours of televised professional and college football, basketball, and hockey games found that a gambling reference, promotion, or commercial occurred every four minutes on average. (Jeremy B. Merrill, Jonathan O'Connell, and Luke Connors, Washington Post)

Tech

U.S. law enforcement warns of “anti-tech extremism” as AI hatred grows: In the wake of attacks on CEOs, a nationwide protest movement targeting data centers, and increasing concerns about AI job replacement, federal intelligence and domestic law enforcement agencies are circulating reports with a new domestic target in mind: anti-technology extremists. (Daniel Boguslaw, Wired)

USDA is using AI, but doesn’t have the required controls to manage risks, watchdog finds: The Agriculture Department is using AI to identify risks in the supply chain, estimate yearly corn and soybean yields, and make recommendations during the permitting process. But according to an inspector general review, the department doesn’t have all of the required cybersecurity and governance controls to keep that technology in check. (Natalie Alms, Government Executive)

Congress wants to steamroll state robotruck laws: Buried in Congress’s massive transportation bill is a provision pushed by the autonomous trucking industry to override state safety rules for self-driving trucks, buses, and other commercial vehicles. (Luke Goldstein, Katya Schwenk, and Freddy Brewster, The Lever)

Health Care

HHS refuses to say what an anti-vaccine activist is doing at the agency: Controversial anti-vaccine activist David Geier is still working at HHS, and the agency is still refusing to specify exactly what he’s doing. In mid-April, HHS Secretary Robert F. Kennedy Jr. told the Senate Finance Committee that he would give them a copy of Geier’s contract. According to a member of the committee, he still hasn’t. (Anna Merlan, Mother Jones)

Short naps, long hours: how autism clinics squeeze Medicaid dollars out of preschoolers: Across the U.S., where treatment for autistic children was once rare, thousands of clinics have sprung up, turning a once obscure therapy into a multibillion-dollar industry. This rapid expansion has played out with little regulatory oversight and brought allegations of children being harmed by profit-motivated practices. (Sarah Kliff and Margot Sanger-Katz, New York Times)