Trump's headline headaches

President Donald Trump is convening the first Cabinet meeting since Markwayne Mullin was confirmed as DHS secretary. But it's also the first confab since Trump launched a military operation against Iran — a topic that is sure to dominate much of the conversation. And the headlines swirling around aren't friendly for Trump: gas prices are still surging and polling shows sinking public support. Playbook's Jack Blanchard and White House reporter Megan Messerly discuss the stakes surrounding the Iran operation.

Democrats got more big wins on Tuesday night, flipping two legislative seats in reliably red Florida, including the district containing President Donald Trump’s Mar-a-Lago home. The wins don't dent Florida Republicans' supermajority, but they mark more performances for Democrats that have defied expectations ahead of the pivotal midterm elections. Playbook's Jack Blanchard and White House Bureau Chief Dasha Burns discuss the warning signs for Republicans, and a notable Trump absence.

A Russian oil tanker is steaming toward the Caribbean, most likely destined for Cuba. But that's not really the story behind the ship and its cargo. It’s a message, according to people close to the White House, former ambassadors and Russia observers — a negotiating chit, a provocation designed to force a disproportionate American response while Washington is consumed elsewhere. Playbook's Adam Wren and White House reporter Megan Messerly discuss the geopolitical stakes of Russia's oil play.

Republicans so far have peeled off a handful of Democrats to pass the DHS funding bill in previous votes, but it's still stalled in the Senate. But new demands from President Donald Trump could threaten any progress. Meanwhile, a new push from an influential Democratic think tank wants to help Democrats reclaim political ground on the issue ahead of the midterms. Playbook's Adam Wren and White House reporter Megan Messerly discuss the next turn of the screw on immigrating messaging between both parties.

When Sen. Ruben Gallego (D-Ariz.) won his Senate seat in 2024, he outperformed Kamala Harris in one of the closest battleground states in the country.  Now that he’s in Washington, Gallego’s background is particularly relevant at this moment in politics. With the Iran War intensifying, Gallego offers his perspective as an Iraq War veteran on Trump’s military operation.  And as a Latino Democratic senator of a border state, Gallego has a distinctive outlook on immigration, with criticism for his own party as well as the GOP.  Sen. Gallego sat down with POLITICO’s Dasha Burns on “The Conversation” to talk about voter ID, the 2028 election, and if he thinks Democrats can become the “fun” party again.

Ruben Gallego and Pete Buttigieg are trying to offer Democrats a roadmap back to relevance during the Trump era. Both are veterans, and both have a pitch to voters that goes beyond talking points and cuts through the rhetoric that defines much of the online chatter. Playbook's Adam Wren and White House Bureau Chief Dasha Burns compare notes on their recent conversations with Gallego and Buttigieg and what they reveal about the state of the Democratic Party.

President Donald Trump is still fuming over the lack of support that he has received from allied nations over the course of the war with Iran. That tension will be on full display when Trump welcomes Japanese PM Sanae Takaichi to the White House on Thursday. Japan is one such country that has resisted Trump's calls to get involved in the conflict. Playbook's Jack Blanchard and White House Bureau Chief Dasha Burns discuss Trump's coalition-building challenge. Plus, the administration official who refuses to use email.

VP JD Vance and DNI Tulsi Gabbard — two of the Trump administration's historically biggest war skeptics — are due to deliver remarks on Wednesday. Vance will be at an midterm rally with voters in Michigan as he pitches the administration's affordability agenda. Meanwhile, Gabbard is due before the Senate Intelligence Committee, where her past position on war with Iran and her role in the ongoing operation will be fair game for senators. Playbook's Jack Blanchard and White House Bureau Chief Dasha Burns discuss what Vance and Gabbard might say.

As the Iran war stretches on with no clear end in sight, some on the right are growing concerned that President Donald Trump will be pulled further into the conflict. A further step in the war would risk alienating a key segment of the MAGA base, which helped return Trump to the White House under the promise that Trump wouldn't set off another long-term military engagement. Playbook's Jack Blanchard and White House Bureau Chief Dasha Burns discuss the potential pitfalls for Trump over Iran.

President Donald Trump is calling on about seven countries that rely heavily on oil from the Middle East to band together to open up the Strait of Hormuz. The call to come together to protect the waterway is an escalation of Trump's efforts to expand the scope of the countries involved in the conflict with Iran. But thus far, there has been little to no interest from other countries to join the fight. Playbook's Jack Blanchard and Adam Wren discuss the stakes of Trump's latest gambit.