The Playbook Podcast

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.