Caffeinated Politics

Tom Tiffany is clearly eyeing measurements for new drapes at the Wisconsin Executive Residence. But he first needs to navigate the many political potholes on the road from Hazelhurst to Madison. For all his name recognition in the Northwoods and his reliable conservative bona fides, a statewide governor’s race in Wisconsin is a different beast, one that this year is dominated by deeply entrenched anger at Donald Trump and his supporting class of Republican members of Congress. The geographic gravity may seem to favor Tiffany in the 7th Congressional District, with its sprawling acreage and culturally conservative voting base. But to actually win, he must pull significant numbers from the Milwaukee–Madison corridor. The area that will decide his fate in November.

Running for governor means convincing suburban Waukesha moms, Milwaukee independents, and Dane County moderates that the congressman who built his brand on northern populism and being a lackey for Donald Trump can now suddenly speak fluent ‘statewide coalition’. That’s not impossible, but it’s a translation job that has humbled others before him.

What Tiffany cannot toss aside or wish away is the Trump factor, which is everywhere this year. Let us be honest. The Trump factor is inescapable and highly radioactive. Tiffany foolishly (yet deliberately) aligned himself closely with Trump, which I admit plays beautifully in the northern counties and in GOP primaries. But the statewide general electorate is not going to be conned into accepting a part in the Republican Party theater production of bombastic absurdity. Tiffany would have to thread a needle so thin as to keep the Trump‑loyal base energized without alienating the suburban swing voters who recoil at anything that cozies up to the autocratic Trump. Betting people are placing money on the ditch capturing the congressman in November.

This week, a former staffer in the state senate told me that Democrats will pour money into the race like they’re trying to refill Lake Monona with dollar bills, and national groups will treat Wisconsin as the political equivalent of a swing‑state Super Bowl. The worst place for any of us to be is in front of a television without a recorder to weed out the commercials.

What truly intrigues me as a politico is how Tiffany will message his campaign themes. We know all too well that his congressional persona is built on opposition. From opposing federal overreach, opposing Democratic policies, and even voting against certifying the 2020 presidential election. But here is the thing. A governor doesn’t get to be the “no” guy. A governor has to articulate a vision for schools, roads, budgets, and the thousand unglamorous details of state governance. Tiffany would need to pivot from being an opponent of government to grasping that mature governance is a prerequisite for the job in Madsion. Meanwhile, Wisconsin voters have a long memory for candidates who try to reinvent themselves falsely.

So, I am having this wonderful political conversation with the staffer about Tiffany, and he says that the statewide electorate is the land of one‑point margins, where elections are decided by people who still haven’t forgiven the Brewers for the 2011 NLCS. Then came my deer-in-the-headlights moment. (He explained what that meant with a smile, and I smiled back as if I understood.) His point was that every misstep in politics is magnified, every thoughtless quote becomes a bludgeon, and Tiffany has a dump truck full of embarrassments that simply will not be forgotten by voters.

In short, I expect a tough, hard-run race by Tiffany. But the race for governor is not a simple extension of his congressional district. And once he leaves that cocoon, he is not prepared for the anti-Trump anger that we hold in our part of the state about what his type did to our nation.