October 16, 2025

Ed. note: The Media Update will return Tuesday, October 21.

Trump Administration

Wall Street Journal: Trump Team Plans IRS Overhaul to Enable Pursuit of Left-Leaning Groups

By Brian Schwartz, Richard Rubin, and Joel Schectman

.....The Trump administration is preparing sweeping changes at the Internal Revenue Service that would allow the agency to pursue criminal inquiries of left-leaning groups more easily, according to people familiar with the matter.

A senior IRS official involved in the effort has drawn up a list of potential targets that includes major Democratic donors, some of the people said.

The undertaking aims to install allies of President Trump at the IRS criminal-investigative division, or IRS-CI, to exert firmer control over the unit and weaken the involvement of IRS lawyers in criminal investigations, officials said. The proposed changes could open the door to politically motivated probes and are being driven by Gary Shapley, an adviser to Treasury Secretary Scott Bessent.

Shapley has told people that he is going to replace Guy Ficco, the chief of the investigative unit, who has been at the agency for decades, and that Shapley has been putting together a list of donors and groups he believes IRS investigators should look at. Among those on the list are the billionaire Democratic donor George Soros and his affiliated groups, according to a senior IRS official and another person briefed on the list. It couldn’t be determined upon what grounds Shapley would seek to begin such an investigation.

The Free Press: Exclusive: Trump Admin Tells Banks to Report ‘Domestic Terrorist Activity’

By Gabe Kaminsky

.....An office in the Treasury Department that helps thwart terrorist financing is encouraging banks to report “suspected domestic terrorist activity,” according to two people familiar with the matter who were not authorized to speak publicly.

The Financial Crimes Enforcement Network, also known as FinCEN, is upping its resources to support law enforcement investigations related to potential “domestic terrorist” activity, the people said. That comes as President Donald Trump and his administration vow to crack down on antifa and its possible funding sources after the assassination of conservative activist Charlie Kirk in September.

FinCEN, an office with a budget of around $190 million, helps combat overseas and domestic financial crimes, including international terror financing. Any unlawful activity would be referred to the Department of Justice.

The move is the latest escalation of the Trump administration’s efforts to investigate antifa, which is not a formal entity but a decentralized group of far-left activists. A spokesperson for the Treasury Department declined to comment on the FinCEN actions.

“The question is how they are going to define ‘terrorist activity’ and what banks are supposed to be on the lookout for,” Patrick Sternal, formerly an attorney at the IRS’s Office of Chief Counsel, told me.

Sternal said that the Treasury Department would need to prove tangible connections between funding networks and violence to show criminal behavior. “That’s hard to do,” he said.

Truthout: 3,700 Nonprofits Sign Open Letter Condemning Trump for Targeting Free Speech

By Chris Walker 

.....Thousands of nonprofit organizations have penned an open letter condemning President Donald Trump for signing a memorandum indicating his intention to target the free speech of social justice groups under the guise of combating political violence.

The organizations — more than 3,700 in total — noted that the murder of right-wing political commentator Charlie Kirk in September played a key role in the Trump administration’s directives. Trump has claimed, without evidence, that the gunman was motivated by left-wing ideology, and has seized upon the killing as an opportunity to conduct a sweeping crackdown on leftists and his political opponents.

Politico: State Department revokes visas over Kirk criticism

By Finya Swai

.....The State Department revoked at least six visas from foreigners who publicly celebrated the assassination of conservative activist Charlie Kirk on social media, the department announced Tuesday.

The move has drawn criticism from free speech advocates and prompted a legal defense group to offer free assistance to those affected.

In a post on X, the State Department said it took action against individuals from Argentina, South Africa, Mexico, Brazil, Germany and Paraguay, sharing examples of social media posts celebrating Kirk’s killing during a university debate event in Utah last month.

“The United States has no obligation to host foreigners who wish death on Americans,” the department said. “The State Department continues to identify visa holders who celebrated the heinous assassination of Charlie Kirk.”

Jonathan Turley: Antifa Denial: How a Violent Anti-Free Speech Group Became a Non-Entity in American Politics

.....Politicians and pundits are denying that the left-wing anarchist group exists, mocking President Trump’s designation of Antifa as a terrorist organization.

Rep. Dan Goldman (D-N.Y.) seemed to morph into Hoover before our very eyes, including a posting in which he challenged anyone to “name one member of ‘Antifa.’”

Former House Judiciary Chair Jerrold Nadler (D-N.Y.) was widely ridiculed for denying the existence of Antifa.

Others on the left have joined Goldman in this absurd claim. Late-night host Jimmy Kimmel committed part of his monologue to assure viewers that Antifa is no more than a mythical “chupacabra.” “You understand there is no Antifa,” he said. “This is an entirely made-up organization.”

I have testified about Antifa before Congress, run columns on the organization for over a decade, and wrote a book discussing Antifa. I did oppose declaring Antifa a terrorist organization due to free speech concerns, but I also know that it is very real.

By design, Antifa avoids typical leadership hierarchies and organizational structures. Antifa was first created in the 1920s, associated with the Weimar-era German communist group Antifaschistische Aktion.

Supreme Court

Wall Street Journal: What This Supreme Court Term Means for Future Elections

By Lydia Wheeler

.....The Supreme Court under the leadership of Chief Justice John Roberts has struck down federal limits on how much campaigns can repay candidates for personal loans, how much individuals can contribute during a two-year election cycle, and how much corporations and outside groups can donate. In each instance, the court said the restrictions violated First Amendment free-speech protections. 

The national Republican committees that support House and Senate candidates, along with Vice President JD Vance and former Rep. Steve Chabot (R., Ohio), are now asking the justices to follow that same line of reasoning and allow political parties to spend unlimited amounts to influence federal elections with input from the candidate they are supporting.

The Trump administration has embraced that request and isn’t defending the legality of the federal regulations, prompting the court to appoint an outside attorney to do so.

Parties can spend what they want to promote a candidate, but Congress for more than 50 years has limited how much they can spend in direct coordination with those candidates. Lawmakers believed the restrictions limited excessive spending and were a check on corruption by preventing large donors from circumventing limits on what they can give directly to candidates.

Most of the money goes toward campaign advertisements. Republicans argue it is an unconstitutional burden on their speech to limit consultation with candidates on what those ads say, and when and where they run.

SCOTUSblog: A dive into Justice Kennedy’s new memoir

By Zachary Shemtob

.....Throughout his time on the court, Kennedy wrote some of its most important cases. In the book he discusses several of these.

Citizens United:

Perhaps none of Kennedy’s opinions are as controversial (at least on the left) as Citizens United v. Federal Election Commission. There, a 5-4 court barred certain government limits on campaign spending by corporate interests. In his memoir, Kennedy recognizes that “all of us are concerned with money in politics. But our role was to rule on the constitutionality of a specific piece of legislation passed by Congress.” The justice was particularly disturbed by the government’s position that “if there was an upcoming political campaign and a book was being published, or a movie was being produced, and it was critical of a candidate, then it could stop publication if funded by a corporation.” To Kennedy, “[i]n these campaign finance cases, the voters are the ones with the true power. If they see money coming into campaigns from sources they do not like, they can demand disclosure, and they can choose to vote against the candidate.”

City Journal: Chiles v. Salazar: a Defining Test for the First Amendment

By Colin Wright

.....James Campbell, the attorney representing Chiles, described Colorado’s law as an assault on the First Amendment. “Colorado forbids counselors like Kaley Chiles from helping minors pursue state-disfavored goals on issues of gender and sexuality,” he said, and “prophylactically bans voluntary conversations, censoring widely held views on debated moral, religious, and scientific questions.” Campbell argued that the Tenth Circuit’s ruling had “gutted” the protections for professional speech in National Institute of Family and Life Advocates v. Becerra (2018) and allowed states to turn counselors into “mouthpieces for the government.”

Chiles’s therapeutic approach, Campbell noted, involves speech, and nothing more. She offers no prescriptions, no physical interventions, and no coercion—just conversation. That distinction, Campbell argued, is critical, since the First Amendment protects the exchange of ideas even within a professional setting.

Chief Justice John Roberts and Justice Elena Kagan asked how the legal analysis would change if a therapist combined counseling with medical treatment, such as by prescribing medication or hormones. Campbell said that such situations would be different because speech tied directly to conduct can sometimes be regulated. But pure talk therapy, Campbell suggested, is almost always constitutionally protected.

The Courts

The Hill: Court backs school in ‘Let’s Go Brandon’ ban case

By Lexi Lonas Cochran 

.....The 6th U.S. Circuit Court of Appeals has ruled against two students who sued after a school punished them for wearing “Let’s Go Brandon” shirts, a phrase used to mock former President Biden.  

In a 2-1 decision Tuesday, the court ruled in favor of Tri County Middle School in Michigan, which back in 2022 made two brothers who wore “Let’s Go Brandon” shirts take them off. 

The court said it did not violate the First Amendment because the shirts were targeted for obscenity, not political beliefs.  

Free Expression

Reason ("The Reason Interview with Nick Gillespie"): Can the ACLU Serve Progressives and Conservatives?

By Nick Gillespie 

.....Today's guest is Ben Wizner, deputy legal director at the American Civil Liberties Union (ACLU). He says that President Donald Trump's second term has brought an all-out assault on free speech—targeting comedians, immigrants, universities, and even law firms that take the "wrong" cases.

Gillespie and Wizner put Trump's actions in the context of past presidents and discuss whether the ACLU has strayed from the days of defending the free speech rights of American Nazis in Skokie, Illinois, Unite the Right protesters in Charlottesville, Virginia, and the National Rifle Association (NRA) in New York.

They also discuss the legacy of Edward Snowden, with whom Wizner worked, and whether government spying on citizens has gotten better since the whistleblower revealed illegal mass surveillance of Americans during the Obama administration.

Online Speech Platforms

Ars Technica: OpenAI wants to stop ChatGPT from validating users’ political views

By Benj Edwards

....."ChatGPT shouldn't have political bias in any direction."

That's OpenAI's stated goal in a new research paper released Thursday about measuring and reducing political bias in its AI models. The company says that "people use ChatGPT as a tool to learn and explore ideas" and argues "that only works if they trust ChatGPT to be objective."

But a closer reading of OpenAI's paper reveals something different from what the company's framing of objectivity suggests. The company never actually defines what it means by "bias." And its evaluation axes show that it's focused on stopping ChatGPT from several behaviors: acting like it has personal political opinions, amplifying users' emotional political language, and providing one-sided coverage of contested topics.

The States

New York Times: Florida Grand Jury Hears Evidence in Investigation of Charity Tied to Casey DeSantis

By Patricia Mazzei

.....Prosecutors in Florida brought witnesses before a grand jury in Tallahassee on Tuesday as part of an investigation into a charity tied to Casey DeSantis, the state’s first lady. The investigation is focused on the charity’s $10 million contribution last fall to political committees backing a campaign led by Gov. Ron DeSantis.

One of the witnesses, State Representative Alex Andrade, a Pensacola Republican, led a legislative subcommittee that investigated the charity’s finances this year.

10 WBNS: Investigation reveals Ohio commission struggled to recoup $96 million campaign finance fees

By Rochelle Alleyne

.....An analysis by Ohio Investigates found a troubling trend — almost $96 million of the penalties that the commission has handed out since 1987 remains uncollected.

Those numbers show that about $5.8 million of that money owed is connected to central Ohio candidates, organizations and campaigns. That data also shows that Franklin, Lucas and Cuyahoga counties are among the top three in the state for unpaid fines.

It's an issue that led Secretary of State Frank LaRose to describe the commission as a "toothless organization" in a May 2025 press release.

"They have been fining people and entities for years and not collecting the fines, something close to $100 million in uncollected fines," he said. "Elections have consequences and election law needs to be uniformly enforced."