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Trump sets new scores to settle

May 20, 2026

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By Irie Sentner and Makayla Gray

Presented by

BULLETIN: The Department of Justice just brought charges against former Cuban President Raúl Castro in connection to the deaths of four people in 1996 — an escalation of President Donald Trump’s pressure campaign against the island nation as the threat of military action intensifies. The indictment, which includes multiple other people, alleges conspiracy to kill U.S. nationals, destruction of aircraft and four counts of murder. More from POLITICO’s Kimberly Leonard

THE CATCH-UP

President Donald Trump is presented a football helmet by First Class Cadet Savannah Riera, during the commencement ceremony at the U.S. Coast Guard Academy, in New London, Conn., Wednesday, May 20, 2026. (AP Photo/Jacquelyn Martin)

Despite a recent run of setbacks for Trump, a string of wins this week have him taking a victory lap — and they’re emboldening him to expand his politically risky revenge tour.

The president returned from his Beijing trip last week to surging prices and a plunging approval rating, having made few major breakthroughs with Chinese President Xi Jinping and little movement on ending the war with Iran.

Costs remain high and Trump’s approval low, but the president’s political fortunes have taken on some shine this week.

On Saturday, Julia Letlow and John Fleming advanced to a runoff in Louisiana’s GOP Senate primary, trouncing Sen. Bill Cassidy, a two-term incumbent who sealed his fate five years ago when he voted to convict Trump in his second impeachment trial.

On Monday, the Justice Department announced it settled a $10 billion suit Trump brought against the IRS and said it would establish an unprecedented and controversial $1.776 billion fund to pay alleged victims of “lawfare and weaponization” — a pool that potentially includes Jan. 6 rioters.

And last night, voters ousted Trump’s least favorite Republican, Kentucky Rep. Thomas Massie, and advanced a slate of MAGA candidates in Georgia.

“We won all races last night,” the president gloated to reporters this morning outside Air Force One. The string of victories on Trump’s retribution tour appear to be buoying a desire for new scores to settle.

Trump is now demanding that Senate Republicans fire parliamentarian Elizabeth MacDonough after she ruled that funding for the White House ballroom cannot be included in Republicans’ party-line immigration enforcement bill — doubling down after Majority Leader John Thune called his threats against her “concerning.” “Get smart and tough Republicans, or you’ll all be looking for a job much sooner than you thought possible!” he wrote this morning on Truth Social.

Yesterday, Trump endorsed Texas AG Ken Paxton over incumbent Sen. John Cornyn, whom Trump claims has not been sufficiently loyal despite a sterling record of voting in step with him. Backing the scandal-plagued Paxton is causing some Republicans heartburn. There’s plenty of concern Republicans will be forced to up their spending against Democratic nominee James Talarico in what’s been one of the most reliably red states.

The president kept those vibes rolling this morning, re-upping his threats to seek revenge against Rep. Lauren Boebert (R-Colo.), an “America First” firebrand who broke with the president by pushing to release the Jeffrey Epstein files and campaigning with Massie last weekend. He told reporters today even though “it’s a little late in the race,” he would give a look if somebody raises their hand to run against her. (Boebert, for her part, declared last night on X after Massie’s defeat that “Trump is my President!”)

Trump also turned his ire today to Pennsylvania Rep. Brian Fitzpatrick, a moderate Republican who hails from a must-hold district if the GOP hopes to defend the House majority. Fitzpatrick last week blasted Trump’s ballroom funding request — and Trump has taken notice, issuing a fresh threat to Fitzpatrick before a gaggle of reporters that included Fitzpatrick’s fiancee, Fox News’ Jacqui Heinrich.

“He likes voting against Trump. You know what happens with that — doesn’t work out well,” the president said.

Good Wednesday afternoon. Thanks for reading Playbook PM. Drop us a line at isentner@politico.com and mgray@politico.com.

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7 THINGS YOU NEED TO KNOW

1. BRAVE NEW WORLD: “Inside the next phase of OpenAI’s political strategy,” by POLITICO’s Brendan Bordelon: “The artificial intelligence industry’s push for tech-friendly federal legislation is foundering in Washington. So OpenAI’s top lobbyist and political strategist is pursuing a backup strategy — setting national AI policy by waging a state-by-state campaign. Chris Lehane calls the plan ‘reverse federalism’: With Capitol Hill deadlocked, the company behind ChatGPT is increasingly spending its time lobbying for state legislatures to pass laws on AI safety that the industry can live with. OpenAI’s quest to shape policies … has already found success in California and New York, he said — with Illinois as its next target.”

2. THE FUND FUROR: Two law enforcement officers filed a lawsuit against the Trump administration to block the new $1.776 billion “anti-weaponization fund” on the grounds that it allows Proud Boys and Jan. 6 rioters to receive payment after causing concrete and cognizable harm, POLITICO’s Josh Gerstein reports. Harry Dunn and Daniel Hodges, who both were working during the Jan. 6 Capitol attack, said the fund should be deemed illegal and requested a judge reverse any payments made by the Treasury Department to the DOJ to implement it.

The view from the hill: Speaker Mike Johnson declined to rule out whether any convicted attackers from Jan. 6 would be eligible to receive money from the fund, and refused to say if he would oppose a scenario where they would qualify, per POLITICO’s Hailey Fuchs. “I’m not going to comment on that until it comes up,” Johnson said.

3. IRAN LATEST: Trump says he's “in no hurry” to make a deal to end the war in Iran, also claiming that Israeli PM Benjamin Netanyahu will do “whatever I want him to do” regarding the war, per CBS. U.S. Central Command said Marines today “boarded and searched an Iranian-flagged oil tanker that was suspected of trying to violate the U.S. blockade of Iranian ports.” Meanwhile, Iranian Parliament Speaker Mohammad Bagher Ghalibaf warned of escalation, saying in a recorded address that “we are in a war of wills.”

Help on the way?: NATO allies are informally considering a role to help reopen the Strait of Hormuz, NATO Secretary-General Mark Rutte said today, per Bloomberg’s Andrea Palasciano.

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4. CUBA WATCH: For Cuban Independence Day, Secretary of State Marco Rubio shared a five minute video of him speaking entirely in Spanish and proposing a new relationship between the U.S. and Cuba. He said the Trump administration is offering “$100 million in food and medicine for you, the people,” in the video, “but it needs to be distributed by the ‘Catholic Church or other trusted charitable groups. Not stolen by GAESA to sell in one of their stores,’” per Axios’ Marc Caputo. This came hours before the DOJ indicted Castro.

On that note: Trump emphasized how he views his relationship with Hispanics, saying “if we had Jesus Christ come down and count the votes, I would have won California because I do great with Hispanics,” per USA Today’s Joey Garrison, who added “Trump lost California by 20 points in 2024 and 29 points in 2020,” via X.

5. MORE FALLOUT FROM LAST NIGHT: Another lesson from the Massie and Cornyn sagas? The gun lobby’s influence is waning, POLITICO’s Sam Benson reports. Giffords, a gun safety advocacy group cofounded by former Rep. Gabby Giffords (D-Ariz.), is sending a memo to all Republican members of Congress today — first shared with POLITICO — noting that pro-firearm groups sat out both the Massie and Cornyn primaries, even as the two represent opposite wings of the pro-gun spectrum.

6. MORE RFK SHAKEUPS: HHS Secretary Robert F. Kennedy Jr. fired two leaders of the U.S. Preventive Services Task Force to “avoid uncertainty that could jeopardize the validity of future Task Force actions,” in letters sent out last week, NYT’s Maggie Astor reports. The task force, which makes recommendations and decisions on medical services, underwent a “direct review” of appointments “‘to ensure clarity, continuity, and confidence in the Department’s exercise of its appointment and supervisory responsibilities, and to protect the integrity of the Task Force’s work.’” The letters say the terminations are not related to the leaders’ performance and that they are free to reapply for positions on the task force.

7. FOR YOUR RADAR: “Deputy British Ambassador to U.S. Leaves Job Abruptly,” by NYT’s Stephen Castle: “In a statement of just six words, giving no indication of the reason for his abrupt departure, Britain’s Foreign Office said simply: “James Roscoe has left his post.” Mr. Roscoe’s official biography on a British government website was updated on Wednesday morning to say that his role as deputy head of mission in Washington ended this month. Mr. Roscoe’s departure is the latest rupture at the embassy, which was thrust into the spotlight when the former ambassador, Peter Mandelson, was fired last September,”

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TALK OF THE TOWN

IN MEMORIAM — “Barney Frank, who led sweeping financial reforms, dies at 86,” by POLITICO’s David Cohen: “Frank came out to a Boston Globe reporter in May 1987, a first for a sitting member of Congress. … In 2012, he became the first member of Congress to marry someone of the same gender, longtime partner James Ready, in a wedding officiated by Massachusetts Gov. Deval Patrick. …

“During Frank’s four years as chair of the House Financial Services Committee, he helped steer Congress’ reaction to the 2008 subprime mortgage catastrophe, which had sent the economy spiraling into recession. The 2010 Dodd-Frank Act, which was designed to help the financial system avoid a repeat of that disaster, bore his name and brought a lot of heat his way from Wall Street.”

MEDIAWATCH — James Murdoch, the son of conservative media mogul Rupert Murdoch, is buying roughly half of Vox Media for more than $300 million, NYT’s Benjamin Mullin and Jessica Testa report. The acquisition includes the company’s podcast network and New York magazine.

THAT’S SETTLED — “He Was Jailed Over a Charlie Kirk Post. The Sheriff Now Owes Him $835,000,” by NYT’s Rick Rojas: “A Tennessee man who was jailed for 37 days over a Facebook post he shared after the killing of Charlie Kirk agreed on Wednesday to a $835,000 settlement with the sheriff’s office that detained him, his lawyers said. … In the posts, he shared memes that accused Mr. Kirk’s organization, Turning Point USA, of perpetrating hate and another that included past comments from President [Donald] Trump about moving past a school shooting.”

OUT AND ABOUT — U.S. Global Leadership Coalition hosted Republican chiefs of staff and conservative foreign policy leaders at the American Trucking Association last night. SPOTTED: Norm Coleman, Kelley Currie, Alexander Gray, Heather Nauert, Samah Norquist, Jody Olson, Paul Teller, Charity Wallace, Amy Albro, JT Jezierski, Alex Fink, Susan Adams and Liz Schrayer.

— The Science Coalition’s “The Science of Transportation” event was hosted last night and sponsored by CRH at 101 Constitution Ave. NW. SPOTTED: Rep. Rick Larsen (D-Wash.), Seval Oz, Jake Dowd, Ryan Lindsey and Alexandra Skores.

— Democracy Defenders hosted a reception for its Defend The Vote town hall on Capitol Hill. SPOTTED: Reps. Lori Trahan (D-Mass.), Brad Schneider (D-Ill.) and Joe Morelle (D-N.Y.), Marina Jenkins, Stephen Spaulding, Adam Smith, Jon Golinger, Jessica Jones Capparell, Dustin Wahl and David Bond.

— Betsy Williams hosted an event for Sens. Chris Coons (D-Del.) and John Hickenlooper (D-Colo.) at her home in Chevy Chase, Maryland. SPOTTED: Robin Hickenlooper, Tom Moore, Fred Graefe, Dan Hamilton, Angela Lancaster, Chuck Muckenfuss, Dave O’Neil, Carol Pensky, Erin Graefe Dorton and Elizabeth Miller.

BONUS BIRTHDAYS — Lyssa Bell and Calli Cooper of the RSC both turn 30 today.

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