| | | |  | | By Ali Bianco | | Presented by |  | | | With help from Eli Okun, Bethany Irvine and Rachel Umansky-Castro Good Sunday afternoon. I’m Ali Bianco, taking the lead today. As always, inbox is open. INSIDE TRUMP’S WAR ON DRUGS: POLITICO’s Nahal Toosi pens her latest Compass column, digging into President Donald Trump’s war on drugs that has another target in mind: “The first time President Donald Trump tried to push Nicolas Maduro out of power, he wasn’t coy about it. He accused the Venezuelan dictator of stealing an election, stripped U.S. recognition from Maduro’s government, imposed sanctions on Caracas and rallied other countries to pressure Maduro to quit. It didn’t work. “In his second term, Trump is targeting Maduro differently, and his message is, uncharacteristically for Trump, less direct. Even though Trump continues to say Maduro is an illegitimate leader, he has said ‘we’re not talking about’ regime change in Caracas. Instead, he’s emphasizing the long-standing accusations that the strongman is a drug lord and a dangerous criminal. The plan, people familiar with the situation tell me, is to force Maduro out as part of Trump’s ongoing fight against drug cartels.”
|  | DRIVING THE DAY | | | 
Federal agents attempt to keep protesters back outside a downtown U.S. Immigration and Customs Enforcement (ICE) facility on Oct. 5, 2025 in Portland, Oregon. | Spencer Platt/Getty Images | THE CRACKDOWN CONTINUED: A federal appeals court temporarily lifted the block on Trump’s federalization of National Guard troops in Chicago yesterday, but stopped short of green-lighting their deployment in the city, POLITICO’s Gregory Svirnovskiy and Josh Gerstein report. In Portland, where troops are also waiting in the wings, an appeals court appears primed to soon let the deployment move forward. The two cases mark the latest in a series of whiplash-inducing legal battles over Trump’s mass immigration crackdown and efforts to deal with crime in cities led by Democratic mayors — which has at times been brushed back at the lower levels before receiving friendlier rulings from the Supreme Court. But it’s also part of a larger aggressive escalation of interior enforcement that has become the marquee agenda item of Trump’s second term. A raft of favorable Supreme Court emergency decisions this year — stripping protections for hundreds of thousands of immigrants with temporary protections, among them — has given Trump space to increasingly test the reach of his executive authority to enact what he promised to be the largest mass deportation in history. The view from the White House: “The administration is confident that our actions will be upheld as lawful, because at the end of the day, they are lawful,” one White House official granted anonymity to speak candidly told Playbook. “You know, if it has to go to a higher court, it has to go to a higher court.” The military deployments to Los Angeles, Chicago and Portland have been reactive to protests, the official said. Trump has also floated sending troops to other major cities in the future, which the official did not rule out. “Obviously you’ve seen the president wants to and won’t hesitate to protect federal law enforcement officers,” they added. That confidence extends to Trump’s allies outside the White House. “Even these recent court rulings that you might characterize as setbacks, they're going to get overturned,” Ken Cuccinelli, who served as DHS deputy secretary during the first Trump administration, told Playbook. “No other president has done this in our adult lifetimes in terms of how they implement immigration policy.” The National Guard deployment, multiple immigration lawyers and experts told Playbook, is no exception and is poised to be one of the biggest tests of his power. “He’s winning,” Mark Krikorian, director of the conservative Center for Immigration Studies, told Playbook. “He's not going to win every case, I don't think, but he's winning a lot of them, because the immigration law is designed that way.” Aaron Reichlin-Melnick, a senior fellow with the American Immigration Council agreed that the office of the president provides Trump with “an enormous amount of hidden weapons,” which he’s deploying at a scale unseen before. But he also said the resistance to Trump’s immigration agenda isn’t causing the administration to consider pumping the brakes. “It’s causing them to step on the gas pedal,” Reichlin-Melnick said.
| | | | A message from the National Retail Federation: Georgetown University and the National Retail Federation announced the launch of the NRF Business of Retail Initiative at the McDonough School of Business. NRF is endowing the National Retail Federation Chair in Retail Studies, the National Retail Federation Summit, two National Retail Federation MBA Fellows, and research grants. Learn more. | | | | Rise of the resistance: Still, Democratic leaders from Chicago and Portland aren’t backing down from the fight. “I am not afraid. Do I think that he could do it? He might,” Illinois Gov. JB Pritzker said this morning on ABC’s “This Week” when asked whether he worried about Trump potentially coming after him, given the president’s Truth Social post saying he should be jailed. “But as I've said before, come and get me.” Oregon AG Dan Rayfield said Trump’s moves amount to an abuse of power in an interview with Playbook’s own Dasha Burns for “The Conversation” this week. Where this is headed: Any of Trump’s most controversial moves that land on the Supreme Court’s desk will be meeting a different reality than the first few months. Trump began his second administration in the middle of the high court’s last term, and gained significant deference through so-called “shadow docket” decisions. With the new term just kicking off, there’s more time for the court to chew on cases. “Trump’s been fortunate to do a lot of the stuff that he got away with during the shadow docket time. I’m not so sure that will continue happening when the Supreme Court has to sit there every week and hear arguments,” immigration lawyer Charles Kuck told Playbook. But Trump has the time to duke this out in court — and the impact could be far-reaching. “The legal piece will gradually fall away. That may take a little while, like a year and a half, but Trump has started very early in his term,” Cuccinelli said. “There's plenty of time to legally see these through and to permanently eliminate questions on the legal front, all while employing this relatively new tactic.” Democrats are still holding out hope that the rule of law will keep Trump in check. “Look, we've got to rely on the courts to do the right thing. I realize that sometimes that's risky business, especially when some have been appointed by Donald Trump,” Pritzker said on ABC this morning. “But we've seen that even a Trump-appointed judge out in California, on the West Coast, has ruled against the administration.” But Trump has found ways to work around court orders slowing his immigration crackdown in the past. Even while the temporary blocks on troop deployments are in place, Trump’s end goal won’t be stymied, said David Bier, immigration director at the libertarian Cato Institute. “They say you can’t do a National Guard deployment, well, is there some other way to get the military involved?” Bier told Playbook. “There's a million different ways in which you can kind of get to the same outcome under different rubrics. … We haven’t even seen the half of it yet.”
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| | | | SUNDAY BEST … — VP JD Vance on the impending release of the hostages and the war in Gaza, on NBC’s “Meet the Press”: “It really should be any moment now, Kristen. The president of the United States is planning to travel to the Middle East to greet the hostages Monday morning … It's a monumental thing. It's great of course for their families. But I really do think that it shows what happens when you go outside the traditional failed diplomatic route and actually try something new.” More on Vance’s Sunday show appearances from POLITICO’s David Cohen — Speaker Mike Johnson on the extension of the Obamacare subsidies, on “Fox News Sunday”: “The Republicans have already said we were going to have thoughtful conversations, deliberation and debate about continuing the Covid-era Obamacare subsidies. Because they don't expire until Dec. 31. They're trying to pretend like that's a September issue. It never was.” — House Minority Leader Hakeem Jeffries on negotiating with Republicans, on “Fox News Sunday”: “This should be a bipartisan negotiation. … My friends on the other side of the aisle, they seem to believe that health care is an extraneous issue. … It’s a central issue. This is the wealthiest country in the history of the world, and people throughout this country should be able to afford to go see a doctor when they need one for themselves, their family and their children.” — Kamala Harris on Trump’s Justice Department, on MSNBC’s “The Weekend”: “What we see is that the rule of law is very much under attack by this president who thinks that the Department of Justice is his personal lawyer and is basically subverting the will of the people around constitutional safeguards. … I think he has a vengeance campaign, which is, I think, really exposing the petty nature of who he is.” — Supreme Court Justice Amy Coney Barrett on having conversations amid a wave of political violence, on “Fox News Sunday”: “I feel like when I talk to people, people are not happy with the level of polarization in the country and the inability of people to have conversations with those whom they disagree with. And so I guess my hope is that we are at a turning point in a corner where more people want to know how to have those conversations.” TOP-EDS: A roundup of the week’s must-read opinion pieces.
- “Bring Back the Internet Gatekeepers,” by Richard Hanania
- “The Supreme Court Is Giving Liberals an Opportunity,” by Ross Wiener for The Atlantic
- “The Gaza I Knew Is Gone,” by Ghada Abdulfattah for the NYT
- “Six surgeons general: It’s our duty to warn the nation about RFK Jr,” by Jerome Adams, Richard Carmona, Joycelyn Elders, Vivek Murthy, Antonia Novello and David Satcher for WaPo
- “Bari Weiss Still Thinks It’s 2020,” by The Atlantic’s Jonathan Chait
- “How the Supreme Court could aid the GOP's redistricting games,” by Richard Hasen for NBC
- “We Need to Break Up Big AI Before It Breaks Us,” by Asad Ramzanali for TIME
- “Voting for Mamdani Taught Me Why Trump Won,” by Michael Hirschorn for NYT
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President Donald Trump walks on the South Lawn after arriving on Marine One at the White House, on Oct. 10, 2025, in Washington | Alex Brandon/AP | 1. MIDDLE EAST LATEST: Trump will head to Tel Aviv at 3:30 p.m. today, arriving in the Middle East at a tense moment as the ceasefire between Hamas and Israel seems to be holding, but is pending the hostage release and prisoner swap that marks the first phase of the U.S.-brokered peace plan to end the two-year war, AP’s Aamer Madhani and colleagues write. Hamas told Israel that it has 20 living hostages in hand and is ready to release them as early as today, WSJ’s Summer Said and colleagues scooped. They will be exchanged for about 2,000 Palestinians imprisoned by Israel, per NYT’s Isabel Kershner. How it’s playing: Thousands of people have been returning to Gaza City as the fragile ceasefire takes effect, but the area has been ravaged by war and many are returning to find their homes and former lives are gone, NYT’s Liam Stack and Bilal Shbair report. But the families of Palestinian prisoners said they feel “rare happiness” at the imminent exchange, NYT’s Fatima AbdulKarim writes from the West Bank. Preparations are also underway for an influx of critical humanitarian aid into the Gaza Strip, per AP. Order of operations: Trump arrives in Tel Aviv at 2:20 a.m. Eastern time Monday morning, where he will meet with hostage families and deliver remarks to The Knesset around 4 a.m. Eastern. He will then fly to Sharm El Sheikh, Egypt, for a Middle East peace ceremony at 7:30 a.m. Eastern. He will depart Egypt to return to the White House at 10 a.m. Eastern. For your radar: Trump spoke with Ukrainian President Volodymyr Zelenskyy over the phone yesterday, per CBS. “If a war can be stopped in one region, then surely other wars can be stopped as well - including the Russian war,” Zelenskyy said in a post on X recounting the call. 2. SHUTDOWN SHOWDOWN: Trump said yesterday he directed the Pentagon to pay U.S. military troops despite the government shutdown, heading off the prospect of troops missing their paychecks this Wednesday, POLITICO’s Ben Johansen and Jennifer Scholtes report. The Pentagon is redirecting about $8 billion from their research and development accounts to pay the troops. “I will not allow the Democrats to hold our Military, and the entire Security of our Nation, HOSTAGE, with their dangerous Government Shutdown,” Trump wrote on Truth Social. Cutting deep: After reduction-in-workforce orders were sent Friday kicking off mass layoffs across multiple federal agencies, a number of employees at HHS who were initially tabbed to be laid off are now being rehired, POLITICO’s Sophie Gardner reports. Sources said an unspecified number of CDC employees were mistakenly fired through a “coding error.” Where things stand: The Senate remains at an impasse on how to proceed. WSJ’s Lindsay Wise writes “even the ‘Groundhog Day’ jokes are getting old now.” House Democrats will be on the Hill Tuesday for an in-person caucus meeting — but the House remains out and is nearing a month without any votes. The impact: WaPo’s Jacob Bogage and Hannah Natanson break down how the shutdown has already caused flight delays, closed helplines at the IRS, shut off national parks and more — but the effects will only get worse as missed paychecks could cause a consumer spending dip. 3. WEAPONIZATION WATCH: Federal prosecutors met yesterday to square the details of a potential indictment against former Trump national security adviser John Bolton, CNN’s Katelyn Polantz reports. Bolton is under investigation in the U.S. Attorney’s Office in Maryland, and prosecutors there initially pushed back on the investigation against the desires of DOJ leadership, requesting more time to prepare a case by the end of the year. But the office is now discussing potential charges, and whether to subject Bolton to a “perp walk” or otherwise public arrest. Trump vs. James: Lindsey Halligan, Trump’s U.S. attorney in Virginia, faced intense backlash after charging former FBI Director James Comey, but it didn’t deter her from presenting charges against New York AG Letitia James days later, WSJ’s Sadie Gurman and Meridith McGraw write. Halligan “wanted to just get it done,” and will likely bring more charges against James. On the charges: “In the Eye of a Political Storm, a Tiny Yellow House in Norfolk, Va,” by NYT’s Jonah Bromwich and colleagues: “Attorney General Letitia James of New York purchased the $137,000 home for a grandniece who needed tranquillity. Prosecutors say it is an impermissible investment property.” 4. IMMIGRATION FILES: “Trump administration says immigration enforcement threatens higher food prices,” by WaPo’s Lauren Kaori Gurley: “The Labor Department warned in an obscure document filed with the Federal Register last week that ‘the near total cessation of the inflow of illegal aliens’ is threatening ‘the stability of domestic food production and prices for U.S. consumers.’ … The Labor Department’s comments appear to be the first time that the Trump administration has publicly acknowledged that its hallmark immigration policy — sealing the border and deporting undocumented immigrants — threatens labor shortages and higher food prices.”
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| | | | 5. SCOTUS WATCH: The Supreme Court will hear oral arguments Wednesday on a landmark case that could erode what remains of the Voting Rights Act of 1965, NYT’s Abbie VanSickle writes. The case centers around 12 Louisiana voters who challenged the state’s district map, saying that they had been discriminated against as white voters, because state lawmakers took race into account when the map was drawn in 2020. Though figures from such high-profile cases can sometimes become publicly known names, the identities of the 12 voters in this case have largely remained hidden. 6. CALIFORNIA SCREAMIN’: The viral videos depicting California gubernatorial candidate Katie Porter derailing an interview and berating staffers are driving momentum for strategists trying to coax other candidates like Sen. Alex Padilla (D-Calif.) into the race, NYT’s Laurel Rosenhall and Benjamin Oreskes report. “The videos offered fresh evidence of fears expressed behind closed doors by power brokers in Sacramento, San Francisco and Los Angeles: Can a politician who appears so volatile run the state of California?” One political consultant told the NYT that Porter’s record of staff turnover “is the worst kept nonsecret in California politics.” Fun read: “7 times politicians imploded in TV interviews,” by POLITICO’s Aaron Pellish 7. ANATOMY OF AN ENDORSEMENT: Florida AG James Uthmeier was endorsed by Trump to run again next year, a move that initially jolted Florida Republicans but stemmed from Uthmeier’s work on “Alligator Alcatraz” and securing the land for Trump’s presidential library, POLITICO’s Gary Fineout and Kimberly Leonard break down this morning. “The president’s endorsement lowers the possibility of a contentious Republican primary next year and lessens the chance of a full-blown Trump-DeSantis proxy war across the ballot.” 8. DANCE OF THE SUPERPOWERS: China hit back today at Trump’s threat of a potential 100 percent tariff on its products. “We do not want a tariff war but we are not afraid of one,” China’s Commerce Ministry said, per AP’s Ken Moritsugu. Trump threatened to ramp up import costs by Nov. 1 — and a potential meeting between Trump and Chinese leader Xi Jinping is on the rocks after Trump cast doubt on whether it would be productive. “If the U.S. side obstinately insists on its practice, China will be sure to resolutely take corresponding measures to safeguard its legitimate rights and interests,” the Commerce Ministry post said. The bigger picture: POLITICO’s Megan Messerly and Phelim Kine write that the tit-for-tat actions on tariffs this week is “the sharpest escalation in tensions between Washington and Beijing since the two countries slapped triple-digit tariffs on each other this spring and threatens to derail months of quiet efforts to stabilize the relationship” and it “raises fresh doubts about whether Trump, operating with a hollowed-out national security team and a fragmented China strategy, is prepared for Beijing’s latest power play.” 9. THE MAHA AGENDA: The massive backlash to HHS Secretary Robert F. Kennedy Jr.’s calls for pregnant women to avoid taking Tylenol is bringing out a bigger problem — most drugs don’t have enough data on their safety during pregnancy, POLITICO’s Alice Miranda Ollstein reports. State abortion bans are worsening existing barriers to women’s health, including drug trials and other studies, as the legal repercussions loom over scientists. Much of the “gold-standard science” lauded by the administration has become more difficult to test on pregnant women and throwing a wrench in the greater mission to do safety testing.
| | | | Introducing Global Security: POLITICO’s weekly briefing on the policies, regulatory battles and industrial shifts shaping defense and security across continents. We connect what happens in Washington, Brussels and beyond to what gets funded, what gets built and who benefits. Subscribe now to access the free preview edition. | | | | | | | TALK OF THE TOWN | | IN MEMORIAM — “Bart Barnes, a Washington Post journalist for five decades, dies at 87,” by WaPo’s Harrison Smith: “Reflexively self-deprecating, [Bart] Barnes was 87 when he died Oct. 5 at his home in Washington. As a Post reporter, he had covered a little bit of everything: Local news, politics and sports (including an NFL players’ strike), along with cops and courts. … But he found an enduring home on the paper’s obituaries desk, where he wrote thousands of stories about the famous, the infamous and the hardly known.” OUT AND ABOUT — MSNBC hosted its “MSNBCLIVE ‘25: This Is Who We Are” event in New York City yesterday, bringing together dozens of the network’s hosts with members of the MSNBC audience. Hosts Rachel Maddow, Lawrence O’Donnell, Nicolle Wallace, Joe Scarborough, Mika Brzezinski, Martin Sheen and more came together for programming and discussions that focused on the state of the world. NEW PERSONNEL AT PERSONNEL: White House deputy chief of staff Dan Scavino will now also lead the White House Presidential Personnel Office, Trump announced on Truth Social. HAPPY BIRTHDAY: Lara Trump … Chris Wallace … NYT’s Michael Barbaro … Juliegrace Brufke … Tanya Bradsher … CAP’s Stephanie Sutton … Kate Nocera … Megan Cheney … Jamie Hennigan of the National Association of Manufacturers … Collin Berglund … WSJ’s Gary Rosen … Glen Bolger of GP3 … Jorge Guajardo of DGA Group … former U.S. Treasurer Anna Escobedo Cabral … Eric Wilson … Bloomberg’s Anna Edney … POLITICO’s Jack Detsch, Dustin Racioppi and Gaelle Ngadjui … former Reps. Ed Royce (R-Calif.) and Joe Garcia (D-Fla.) … Simon Limage … former Sen. Jake Garn (R-Utah) … Amber Lyons … former Michigan Gov. John Engler … David Oleksak … former acting Labor Secretary Seth Harris … AP’s Alan Suderman … Keifer Wynn of the Office of Personnel Management … Kody Keckler of Rep. Mike Quigley’s (D-Ill.) office … Jack Speer … Rosie Gray … Rabbi Moshe Margaretten Did someone forward this email to you? Sign up here. Send Playbookers tips to playbook@politico.com or text us on Signal here. Playbook couldn’t happen without our deputy editor Garrett Ross and Playbook Podcast producer Callan Tansill-Suddath.
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