Some political candidates run away from controversial presidents. Representative Derrick Van Orden isn't one of them. In Wisconsin's third congressional district, the two-term Republican incumbent is leaning hard into his alliance with Donald Trump, even as national Democrats target the seat in a high-stakes bid to flip control of Congress.
It's a high-risk strategy. Trump's approval ratings in the Badger State sit around 40 percent in recent polling from the Marquette University Law School, and swing district math usually rewards candidates who moderate their image. But Van Orden, a former Navy SEAL known for his abrasive online style, argues that loyalty matters more than political cowardice. He voted with Trump nearly 100 percent of the time in 2025 and secured explicit backing from the White House, while top administration officials have made campaign stops in western Wisconsin to help shore up his base.
The Battleground in the Driftless Area
To understand why this race matters, look at the map. The third district spans the rolling hills of the Driftless Area along the Mississippi River, a region historically friendly to political moderates. Democrat Ron Kind held the seat for 26 years before retiring in 2022, and Barack Obama won the district twice. Yet Trump carried it three separate times in 2016, 2020, and 2024.
Senator Ron Johnson famously called it a bellwether district in a bellwether state. That means you can't predict it using standard party formulas.
On one side stands Van Orden, who rode his Harley-Davidson motorcycle in the Labor Day parade in Readstown and draws fierce loyalty from working-class rural conservatives. On the other side is Democrat Rebecca Cooke, a former small business owner and restaurant server running a rematch campaign after losing to Van Orden by less than three percentage points two years ago.
Cooke is pitching herself as a pragmatic populist. She argues that hitching your wagon to a polarizing executive is a major error when voters are anxious about inflation, economic uncertainty, and foreign policy friction like the unpopular Iran conflict.
Why the Incumbent Won't Back Down
Van Orden doesn't care about standard advice. He views distance from the party leader as a betrayal. Before flying to Dallas for a high-profile Republican convention appearance, he made his philosophy clear. Loyalty is missing in modern politics. He believes turning out the conservative base beats trying to win over centrist skeptics who might never vote for a Republican anyway.
That calculus is backed by outside money and heavy hitters. Elon Musk’s America PAC has funneled funds into the race, and Cabinet members like Health Secretary Robert F. Kennedy, Jr., FBI Director Kash Patel, and CMS Administrator Mehmet Oz have dropped into the district to campaign alongside him.
Critics call it doubling down on extremism. Van Orden calls it authentic leadership. He claims his aggressive social media presence is just a tool to push back against death threats and hostile opponents rather than back down from a fight.
What This Means for the Midterms
This Wisconsin showdown exposes a broader dilemma for the GOP. Do incumbents in competitive territory tie themselves to a dominant leader with mixed suburban polling, or do they risk alienating the grassroots engine that powers turnout?
Cooke is banking on voter fatigue with political polarization, hoping to pull enough independent and soft Republican voters who want a reset. Van Orden is betting that raw tribal loyalty and economic populism will punch through the noise.
November will settle the bet. Until then, the ground war in western Wisconsin remains a glaring preview of how nationalized politics plays out kitchen-table style in rural America.
