Trump's Top Pick: Tiffany Charges Into Wisconsin Governor's Race

Paul Riverbank, 1/29/2026Trump backs Tiffany in Wisconsin, igniting a fiercely Midwestern, unpredictable governor’s race.

Ask a kid from Minocqua or a diner owner off Highway 51 about Tiffany, and you’ll get a shrug and a story: he’s a farmer, used to early mornings and late nights. The kind who’ll show up at the town fair with his sleeves rolled up, probably more comfortable in scuffed boots than a suit. He’s plainspoken—some say blunt, others say refreshing. Whatever your take, you can’t accuse him of playing coy.

Of course, “plain talk” has a new cast these days, especially when Donald Trump enters the frame. Trump, never one for half-measures, went straight to his Truth Social account and delivered what he called a “Complete and Total Endorsement” of Tiffany. For the Wisconsin GOP, that’s a shiny seal of approval. Trump’s post was one part pep talk, one part sales pitch: hardworking, family-first, America-made. Like something you might see stitched on a trucker’s cap at the county fair. The message wasn’t subtle—“HE WILL NEVER LET YOU DOWN!” Trump wrote, all caps and exclamation, as if the digital ink could shout.

Tiffany was quick to tip his hat back. Online, he echoed Trump’s calls for a stronger economy and a sealed border, evoking campaign trail greatest hits: tax cuts, local jobs, manufacturing pride, energy independence. It all lands somewhere between nostalgia and blueprint—drawing on the kind of talk that plays well, especially when you consider how razor-thin Wisconsin’s margins can be. You get the sense that every radio ad, every handshake at the farmers’ market, might be the difference.

He’s no stranger to the stakes, having stepped into Congress in 2020 when Sean Duffy left office. Folks in his district know his talking points by heart: keep government out of your pockets, protect small businesses, and tend to the family farm. For his core supporters, Tiffany is the sort of candidate you can spot eating Friday night fish fry out in Tomahawk, not just shaking hands in Madison.

Postcards from across the Mississippi tell a different story. There’s Jesse Ventura up in Minnesota—navy vet, wrestling showman, former governor, never afraid to grab the mic. Recently, he took a detour into what sounded like satire on a podcast: “If Trump hates Minnesota so much, maybe we should just join Canada.” Hyperbole? Sure. But under the wisecracks, a trace of real irritation. Ventura pointed to a tragic incident in Minneapolis to make his case—echoing the frustration some Minnesotans feel about federal attention, or lack thereof.

In classic Ventura style, the punchlines kept coming: “Let’s call Ottawa, see if they want us!”—joking, but also feeding off a long Minnesota tradition of political independence and a healthy disregard for outside labels. From the days of Humphrey and Wellstone, nonconformity runs deep up there. Across the region, you still meet voters with campaign buttons from politicians who never quite fit neatly into any party tent.

Sometimes I wonder if the only thing these states have in common is the sound of tractors in the spring. In Wisconsin, Trump’s embrace of Tiffany is a clarion call for the right—steady, familiar, reliable. Next door, Ventura’s wisecracks keep the chattering classes guessing and the social media feeds humming. Different approaches, but underneath, a familiar theme: Midwestern voters don’t much like being told who they are.

It’s shaping up to be an unpredictable season on both sides of the St. Croix. Rallies will spill into fairgrounds, kitchen tables will host political arguments as heated as any barn dance. In the end, the heartland’s biggest question—stick with what you know, or try something off the beaten path—will hang over everything.

Whatever the outcome, one thing’s certain: these stories will keep coming, often in unexpected shapes and colors, as the Midwest does what it always has—think out loud and cast its vote, loudly and often, for whichever future seems to fit best.

They say the political winds in Wisconsin change quickly—one minute you’re watching the corn sprout, the next there’s a campaign sign on every fourth fence post. This year, Tom Tiffany’s got the wind at his back, or so his supporters hope. When Tony Evers, the Democratic governor, decided not to run again, you could almost hear the collective intake of breath across the state: Who’d step forward? From the sandy woods up north, Tiffany’s name drifted south, as familiar to locals as deer season or the first frost.Ask a kid from Minocqua or a diner owner off Highway 51 about Tiffany, and you’ll get a shrug and a story: he’s a farmer, used to early mornings and late nights. The kind who’ll show up at the town fair with his sleeves rolled up, probably more comfortable in scuffed boots than a suit. He’s plainspoken—some say blunt, others say refreshing. Whatever your take, you can’t accuse him of playing coy.Of course, “plain talk” has a new cast these days, especially when Donald Trump enters the frame. Trump, never one for half-measures, went straight to his Truth Social account and delivered what he called a “Complete and Total Endorsement” of Tiffany. For the Wisconsin GOP, that’s a shiny seal of approval. Trump’s post was one part pep talk, one part sales pitch: hardworking, family-first, America-made. Like something you might see stitched on a trucker’s cap at the county fair. The message wasn’t subtle—“HE WILL NEVER LET YOU DOWN!” Trump wrote, all caps and exclamation, as if the digital ink could shout.Tiffany was quick to tip his hat back. Online, he echoed Trump’s calls for a stronger economy and a sealed border, evoking campaign trail greatest hits: tax cuts, local jobs, manufacturing pride, energy independence. It all lands somewhere between nostalgia and blueprint—drawing on the kind of talk that plays well, especially when you consider how razor-thin Wisconsin’s margins can be. You get the sense that every radio ad, every handshake at the farmers’ market, might be the difference.He’s no stranger to the stakes, having stepped into Congress in 2020 when Sean Duffy left office. Folks in his district know his talking points by heart: keep government out of your pockets, protect small businesses, and tend to the family farm. For his core supporters, Tiffany is the sort of candidate you can spot eating Friday night fish fry out in Tomahawk, not just shaking hands in Madison.Postcards from across the Mississippi tell a different story. There’s Jesse Ventura up in Minnesota—navy vet, wrestling showman, former governor, never afraid to grab the mic. Recently, he took a detour into what sounded like satire on a podcast: “If Trump hates Minnesota so much, maybe we should just join Canada.” Hyperbole? Sure. But under the wisecracks, a trace of real irritation. Ventura pointed to a tragic incident in Minneapolis to make his case—echoing the frustration some Minnesotans feel about federal attention, or lack thereof.In classic Ventura style, the punchlines kept coming: “Let’s call Ottawa, see if they want us!”—joking, but also feeding off a long Minnesota tradition of political independence and a healthy disregard for outside labels. From the days of Humphrey and Wellstone, nonconformity runs deep up there. Across the region, you still meet voters with campaign buttons from politicians who never quite fit neatly into any party tent.Sometimes I wonder if the only thing these states have in common is the sound of tractors in the spring. In Wisconsin, Trump’s embrace of Tiffany is a clarion call for the right—steady, familiar, reliable. Next door, Ventura’s wisecracks keep the chattering classes guessing and the social media feeds humming. Different approaches, but underneath, a familiar theme: Midwestern voters don’t much like being told who they are.It’s shaping up to be an unpredictable season on both sides of the St. Croix. Rallies will spill into fairgrounds, kitchen tables will host political arguments as heated as any barn dance. In the end, the heartland’s biggest question—stick with what you know, or try something off the beaten path—will hang over everything.Whatever the outcome, one thing’s certain: these stories will keep coming, often in unexpected shapes and colors, as the Midwest does what it always has—think out loud and cast its vote, loudly and often, for whichever future seems to fit best.