Today's five.

Kentucky Rep. Thomas Massie faced the toughest primary challenge of his career Tuesday, squaring off against Trump-backed retired Navy SEAL and fifth-generation farmer Ed Gallrein in what has become the most expensive House primary in U.S. history, with more than $32.6 million in total spending. Massie, who has represented Kentucky's 4th Congressional District since 2012, broke with Trump on key second-term issues and led the push to release Jeffrey Epstein investigative files, drawing sustained presidential opposition. The deeply conservative district has been held almost uninterruptedly by Republicans since the 1960s. The outcome serves as a gauge of Trump's ability to enforce loyalty within the GOP heading into the 2026 midterms.

The Senate voted 50-47 Tuesday to advance a war powers resolution that would direct President Trump to withdraw U.S. forces from Iran unless Congress authorizes the conflict to continue. The breakthrough came as Sen. Bill Cassidy (R-LA), days after losing his Republican primary to a Trump-backed challenger, cast his first-ever "yes" vote on the measure after opposing it seven previous times. Cassidy joined Republicans Rand Paul, Susan Collins, and Lisa Murkowski in crossing party lines. Citing a lack of White House and Pentagon transparency about Operation Epic Fury, Cassidy said constituents — including Trump supporters — have expressed concern about the war. The vote marks the first time the chamber has advanced the resolution since the conflict began in February.

The Congressional Black Caucus and NAACP on Tuesday called for a boycott of public universities in Southern states by athletes and supporters, tying their opposition to GOP-led redistricting efforts they say dilute Black voting power. House Minority Leader Hakeem Jeffries joined fellow CBC members in opposing a bill that would establish a national framework for college sports, using the legislation as leverage to draw attention to gerrymandering in the South. Right-leaning coverage frames the caucus's position primarily as an unusual intersection of sports policy and electoral politics, while left-leaning outlets emphasize the voting rights dimension as the central driver of the action.

The Justice Department has agreed to permanently drop all tax claims against President Donald Trump, his sons, and the Trump Organization as part of a settlement resolving Trump's $10 billion lawsuit against the IRS over the leak of his tax returns. A one-page document posted to the DOJ website states the U.S. is "forever barred and precluded" from examining or prosecuting those current tax issues. Democratic lawmakers and ethics watchdogs have criticized the arrangement, calling it corrupt and warning it could function as a slush fund for the president and his allies. Analysts describe the settlement as an extraordinary use of executive power with broad implications for presidential accountability.

David Jolly, running as a Democratic candidate for Florida governor, has expanded his senior leadership team with three new hires: nationally known Democratic strategist Joe Trippi, public policy adviser Kimberly G. Jackson, and Miami-Dade Democratic strategist Christian Ulvert. Trippi, 69, is best known for managing Howard Dean's pioneering 2004 presidential campaign. The additions signal an escalation in Jolly's gubernatorial bid as the race intensifies. Trippi's involvement in particular lends the campaign a high-profile national profile, given his decades of experience in Democratic politics at the presidential level.