Bruce Murphy
Murphy’s Law

Tom Tiffany’s Terrible Day

His press conference was supposed to be about taxes. How did it go so terribly wrong?

By - Jan 28th, 2026 04:15 pm

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Tom Tiffany had everything prepared. Monday was going to be a big day for his campaign for Wisconsin governor. He had called a press conference for that afternoon to unveil his proposal for property taxes, often called the most hated of taxes.

On “day one” as governor, Tiffany promised, he would repeal the “400-year tax hike” by Gov. Tony Evers and pass a freeze on property taxes. It was a simple, easy-to-understand proposal that should grab the voters attention and he had a press release ready to go to all the media as soon as he finished his speech.

Except. This was no ordinary time in America or Wisconsin. This was just two days after federal ICE agents had killed Alex Pretti in Minneapolis and videos of the killing were being watched by citizens across the land. In Wisconsin, where Pretti attended elementary and high school, and where his family still lives, people who knew him were posting remembrances and telling the media what a wonderful person he was.

Tiffany is a member of Congress, which provides the funding for ICE, and a strong supporter of President Donald Trump’s immigration policies, and should have expected questions about Pretti’s killing, the most talked about issue in America. But he clearly didn’t.

When asked by reporters about this, Tiffany called for a “full investigation” of the shooting, saying “Lets get all the facts on the table and make sure to make a reasoned decision.” He also suggested cellphone videos can often be “grainy” and hard to interpret.

Except. The videos of Pretti’s killing were clear as crystal and showed they took his gun away and had him disabled and down on the ground and then shot him as many as ten times.

Had he watched the video, Tiffany was asked. No, he said. “I have not watched the video.”

Seriously?

“That can’t be true,” one Republican who is not backing Tiffany told Urban Milwaukee. “Every politician reads the Wall Street Journal and it’s been covering the issue with front page stories every day since Saturday, including a detailed break down of the videos. There’s no way he hasn’t seen it.”

Democrats heaped ridicule on Tiffany, with Democratic Party of Wisconsin Chair Devin Remiker, calling him at best, a clueless coward and at worst a liar. Either way, hes unfit to serve as governor of Wisconsin.”

Mike Browne, Deputy Director of the liberal group, A Better Wisconsin Together piled on, declaring that Tom Tiffany continues to prove there are no depths to his ignorance.”

Far worse for Tiffany, his hard-to-believe statement was reported across the state by print and broadcast media. As for his property tax plan, it got little coverage. To put it bluntly, Tiffany blew it.

This is a guy who waited months before announcing his run for governor, which meant he would have to give up his seat as Wisconsin’s 8th District Congressman. He made sure to line up his support, including from the state’s biggest conservative donors, Diane Hendricks and Elizabeth and Richard Uihlein, who all gave the maximum donation to his campaign.

Tiffany sounds like a Wisconsin guy, and has a pleasant, measured style in interviews, seemingly unruffled by tough questions. But it’s a far different thing being a congressman than running for governor. They can go months without any challenging media coverage in Wisconsin and since 2011 have served in gerrymandered districts that almost guarantee their reelection (with the exception of the Third District now held by Derrick Van Orden). The governor’s race, as it heats up, could mean daily questions from the media.

Tiffany had made no secret of his hope that Trump would endorse him and sure enough that endorsement came today, with the president praising Tiffany, with no shortage of capital letters, as a “very successful Businessman, Family Farmer, and State Legislator, prior to becoming a distinguished United States Congressman,” and “a Proven Leader who has dedicated his life to serving his Community.”

So Tiffany had to be careful not to alienate Trump by criticizing him in any way. After Trump’s invasion of Venezuela, the congressman loyally repeated the president’s lie that thousands of Americans lost their lives because of drugs coming into this country from Venezuela. But most voters pay little attention to foreign affairs, much less the specifics of the international drug trade, so Tiffany needn’t have worried about blowback from his comment.

But the ICE invasion of Minneapolis has gotten national attention, with the conservative Wall Street Journal’s editorials condemning it. Tiffany needed a very carefully crafted statement along the lines of what Wisconsin’s Republican Congressman Tony Wied offered, calling Pretti’s death a tragedy and asking people to tone down the rhetoric while awaiting a full investigation.

Most Democrats probably found Wied’s full statement disingenuous: he seems to be blaming Pretti for what happened without specifically saying so. But it sounds Shakespearean compared to Tiffany’s lame comment that he didn’t watch the video, which few voters of either party will believe. It’s hard to believe Tiffany’s media advisor didn’t make sure he had a very judicious statement about the turmoil in Minnesota.

The Trump endorsement probably helped convince Republican Josh Schoemann to withdraw from the race. But Tiffany was likely to win the primary anyway. Far more important is that the endorsement will hurt him in the general election, as it hurt Brad Schimel in last year’s April election for the state Supreme Court that the conservative lost by 10 percentage points. Tiffany’s strategy of working so hard to win Trump’s favor seems unwise. And his lame answer on the Pretti video suggests the candidate is not yet ready for prime time.

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Categories: Murphy's Law, Politics

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