In Wisconsin, a growing number of conservative voters do not support Republican Donald Trump for president. But are they seriously considering voting for Democrat Kamala Harris?
A chance to reflect on the candidates
The decision was playing out for some of them over plates of salmon and brussels sprouts, at a debate watch party at the downtown Milwaukee Club. About 20 people met there by invitation of Craig Peterson, a veteran GOP strategist who doesn’t support Trump.
“This is an event that I've really been doing since 2016. I try to bring together an ambidextrous group of people who are moderates, conservatives, progressives, apolitical people, and we sit around a table, and we have dinner, and we share our observations, and we laugh. There's no meanness, there's no bullying,” he says before it starts.
Peterson said about half of the people at the gathering identify as Republicans, and the other half he’d consider Democrats. But he also says only two are strong Trump supporters.
Tory Lowe is one of them. He’s an activist and radio host in Milwaukee. He says he voted Democratic his whole life, including for Barack Obama, but most recently went third party in 2020. He says that he “started being turned off by the extreme left.”
“I don't like what’s going on with the open borders. I don't like what's going on in Chicago with the sanctuary city idea. In New York, I got advocates that reach out to me and tell me what's going on over there,” he says. “I really honestly want to believe that we can get the best out of everybody that wants to come to America, but you got to come through a process, and it's got to be a legal process.” He says he’s “definitely leaning towards Donald Trump, 100%.”
Peterson, on the other hand, is currently the state’s director of “Haley Voters for Harris.” It’s a group that’s trying to convince the nearly 77,000 voters in Wisconsin who chose former U.N. Ambassador Nikki Haley in the Wisconsin Republican presidential primary in April to vote for Harris. They’re also targeting the nearly 30,000 additional Wisconsinites who voted for other non-Trump Republican presidential candidates. They’re focusing on “suburban, educated voters in the counties surrounding Milwaukee.” These are places that are heavily Republican but where there’s been waning support for Trump in recent years.
Peterson is aiming to convince them of what he already believes: that Trump is not fit to be president again. “Donald Trump has over a nine- year history with us. We all know who he is.. And I think many of us still have PTSD of those four years that he was in office, you know, waking up every morning with that pit in your stomach, never knowing what the hell this crazy man was going to do or say or tweet.”
“We've seen him after he lost an election,” Peterson continues. “We saw him try to steal it using illegal means. First president to ever do that. It's just absolutely unconscionable that people would even consider him giving him the keys to the Oval Office again.” Peterson also disagrees with how Trump handled the COVID-19 pandemic. “It's just incredible, again, that members of the Republican Party would even consider him as their flag bearer. I can't believe it,” Peterson says.
Debate provides a nudge towards Harris for some
At the debate watch party, it’s remarkably quiet until the commercial breaks, when Peterson nudges the onlookers to discuss their takes.
“I find myself disliking her [Harris] less,” says David Irwin, a conservative small company CEO.
“She’ll take it. She’ll take it,” another partygoer responds.
After the debate, Irwin describes himself as a possible Harris voter in November.
While Irwin has trouble with Harris’ economic policies, he says he is more concerned with Trump’s divisiveness, failure to defend allies and his lying about the 2020 election.
“I think it would help for me and a lot of other people, if [Trump] said that, if he lost this election, he would accept it, and he would say that, ‘yes, indeed, the United States of America runs free and fair elections,’ by golly. We're a shining beacon to the world as far as how democracy works. We can't go around criticizing our own elections.”
Irwin says if he does muster up a vote for Harris in November, “I would want her not to be able to get done lots of the things that she would like to do. So, I'll probably vote for Republicans in most of the other races, if not all of them.”
Peterson thinks Harris’ debate performance Tuesday will help woo conservatives like Irwin to actually vote for her. “It's very easy for us to make the argument and the point that she is the better candidate. No question about it,” Peterson says.
Polling shows more Wisconsin conservatives leaning towards Harris
The Marquette Law School poll released on Sept. 11 — with data collected before the debate— showed nearly 12% of conservatives saying they would vote for Harris, up from 6% who said they’d support Biden in June. Eight percent of people who identified as “very conservative” say they’d vote for Harris, up from 1% who said they’d vote for Biden in June.
That’s not surprising to James Wigderson, a Never Trumper from Waukesha who writes mostly about politics, but also about culture and other items.
READ: A Wisconsin ‘Never Trumper’ looks beyond politics with ‘Life Under Construction’
He likes that Harris says she wants a strong military, supports Ukraine being able to defend itself and supports the NATO Alliance. “I may not agree with any of her domestic policies, but I'll certainly agree with her foreign policy, and she's not going to raise a mob to come threaten the US Senate when she doesn't get something to go her way.”
Wigderson also says policy-wise, Trump is not hitting the high notes for conservatives. “We can run down the list of things that Donald Trump is for that are not very conservative. He's for high tariffs. That is not a conservative position. A free market conservative does not support high tariffs. He’s abandoned the pro-life position, well, once you abandon the pro-life position, then there's no difference between Donald Trump and Harris on the issue.”
“So, what are you voting on?” asks Wigderson, “well, you're voting on whether or not you've got a candidate that is a threat to the Constitution, [that] has used political violence to obtain his goals back on January 6, and is that somebody that conservatives want to vote for? And the answer is no.”
A national "permission structure"
Nationally, there has been a parade of Republicans who say Trump is unfit to be president again and who have gone so far as to endorse Harris. That includes former vice president Dick Cheney and his daughter former Congresswoman Liz Cheney and 200 former staffers for Republicans George W. Bush, John McCain and Mitt Romney.
“So, the interesting thing about these endorsements, is that it grants-- it's a permission structure,” says Wigderson. “If you see other people that are like-minded voting the way that you would be inclined to vote but are reluctant to, once you're granted that permission, I wonder how many…will follow?”
Rich Eng is one of those Wisconsin voters following along. He says the endorsements by conservatives such as the Cheneys has granted permission for conservatives like him to vote for Harris. The retired executive says he’s been concerned about the direction of the Republican party under Trump since 2016, but he doesn’t identify as a Never Trumper.
Eng says in order to vote for Trump, he’d need the former president to meet three conditions: “He's got to congratulate Joe Biden on the election. He's got to stop his people and himself from doing all these attacks and bullying and lying. And if he can get the party to pass the immigration bill that Senator James Lankford helped write, then I think I would change my mind. But until then, I'm not supporting him.”
Rich Eng also says that the events of January 6, 2021, and Trump’s felony convictions aren’t total deal breakers. “I believe in rule of law, so he's got to serve his time, but I also believe if somebody can change, and he admits that the election was won fair and square by Joe Biden, he apologizes for January 6, he's got to face the consequence of the law, however that may play out, but. But you know, if he truly demonstrates a change of heart and change in character is denoted by, you know, keeping small promises, then I'm willing to give him a chance.”
He didn't see evidence of any of those things happening in the debate.

A tough decision for some conservatives
Eng says he’ll be voting for Harris in November. But for his wife Lena, who also voted for Haley in the primary, the decision is not so simple. She generally doesn’t agree with Democratic policies, and she’s worried about whether Harris would foster bipartisanship in Congress. “Policy wise, I'm not super comfortable with Kamala, but I think she has better character,” Lena Eng says.
Eng notes, as someone with Taiwanese parents who immigrated to the U.S. in the 1960’s, Trump’s nickname for the coronavirus as the “China virus” or lies about Haitian immigrants eating pets in Ohio are alarming. She describes her own mother-in-law’s story after immigrating to New York from China.
“She grew up and she had to wear a sign that said, ‘I am not Japanese.’ Because of, you know, World War II happening. Words do matter.”
Back in 2020, Eng didn’t vote for Trump or Biden. She wrote in her pick. She says 2024 might be the first time she votes for a Democrat.