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Shady Milwaukee Elections Chief Ousted Six Months Before Election, But Will Her Successor Be Worse?

Milwaukee Election Commission Executive Director Claire Woodall at the city's central count location.
Image CreditNBC News / Youtube 

The leftist mayor of the largest city in swing-state Wisconsin has replaced the controversial elections chief. Now what?


Now that Milwaukee’s controversial election chief has been sent packing, Republicans in critical swing-state Wisconsin are wondering whether the fix will be worse than what previously ailed Milwaukee’s election integrity. 

On Monday, Mayor Cavalier Johnson announced Milwaukee Election Commission Executive Director Claire Woodall is out — just six months before November’s presidential election. Woodall, roundly criticized by conservatives for her handling (or mishandling) of the closely contested 2020 presidential election in battleground Wisconsin, will be replaced by her lieutenant, Paulina Gutierrez, according to the far-left Democrat mayor. 


Johnson spokesman Jeff Fleming told the Associated Press that Woodall’s ouster had nothing to do with her handling of elections but “other issues internal to the election commission office and to city government that raised concern.” What those “issues” are, Fleming didn’t say. 

In an email response to The Federalist’s questions, Fleming said the mayor, fresh off a reelection victory, is statutorily required to appoint approximately two dozen senior administration officials. 

“In three instances, he named someone who was not an incumbent,” the mayor’s mouthpiece said. 

Fleming told WisPolitics that Woodall had written a job description nearly a year ago for a community outreach position, but she refused the position when it was offered to her last week. 

Woodall was out of the office Tuesday on vacation, according to a commission employee. Gutierrez, who has served as Woodall’s deputy for over a year, was said to be in a meeting Tuesday afternoon and did not return The Federalist’s request for comment. 

‘Checkered History’

State Sen. Dan Knodl, a Milwaukee-area Republican who chairs the Senate’s elections committee, said Woodall’s exit was unexpected. 

“I didn’t see it coming or know there was any change in the winds,” he told The Federalist. “Claire has had some checkered history.” 

Indeed. This is the same Milwaukee election administrator who worked closely with a network of leftist “voter rights” activists as part of the Center for Tech and Civic Life’s (CTCL) Covid response grants during the 2020 election. Facebook founder Mark Zuckerberg and his wife, Priscilla Chan, handed out some $400 million ostensibly for “safe elections,” with the lion’s share of the “Zuckbucks” targeting Democrat-heavy cities in swing states such as Wisconsin. In fact, the “Wisconsin-5” cities — Milwaukee, Madison, Green Bay, Kenosha, and Racine — signed contracts with the left-wing CTCL and received nearly 86 percent of the $10 million-plus in grant funds.   

Shortly after the ink dried on the contract, CTCL emailed Woodall, who identified as Claire Woodall-Vogg at the time, to offer “an experienced elections staffer that could potentially embed with your staff in Milwaukee in a matter of days,” according to documents obtained by Federalist Editor-in-Chief Mollie Hemingway.

“The staffer leading Wisconsin’s portion of the National Vote at Home Institute was an out-of-state Democratic activist named Michael Spitzer-Rubenstein. As soon as he met with Woodall-Vogg, he asked for contacts at the Wisconsin Elections Commission and in the other cities,” Hemingway wrote in Rigged: How the Media, Big Tech, and the Democrats Seized Our Elections, her 2021 book on the left’s myriad acts of election interference in 2020. 

Spitzer-Rubenstein had been a longtime Democrat operative in New York, parachuting in particular into the left-led city of Green Bay, where he embedded in the city clerk’s office. Emails show he was given the keys to the room where Green Bay’s absentee ballots were stored. He also had offered to “cure,” or correct, absentee ballot envelopes.  

As Hemingway reported, Spitzer-Rubenstein told Green Bay officials that his organization, the National Vote at Home Institute, had helped cure ballots for other cities in Wisconsin.

“We have a process map that we’ve worked out with Milwaukee for their process. We can also adapt the letter we’re sending out with rejected absentee ballots along with a call script alerting voters. (We can also get people to make the calls, too, so you don’t need to worry about it.),” the activist explained in an email to Green Bay elections officials. 

‘Flair for Drama’

As The Federalist has reported, in the wee hours of Nov. 4, 2020, long after the polls had closed in the Nov. 3 presidential election, Woodall announced a batch of tens of thousands of votes had finally been counted. The vast majority of the votes were for Democrat Joe Biden, helping to give him an extremely narrow victory over Republican President Donald Trump in pivotal swing-state Wisconsin. 

“Damn, Claire, you have a flair for drama, delivering just the margin needed at 3:00 a.m.,” wrote Ryan Chew of the left-leaning Elections Group in an email to the city elections chief. “I bet you had those votes counted at midnight, and just wanted to keep the world waiting!”

Woodall LOL’d about 10 minutes later in an email response to Chew. 

“I just wanted to say I had been awake for a full 24 hours!” the Milwaukee elections chief wrote. 

Woodall told the Milwaukee Journal Sentinel that she “read Chew’s email at the time as a joking way to note the state’s results couldn’t be called until Milwaukee’s total came in.” She claimed she was “kind of uncomfortable” with Chew’s choice of words and shouldn’t have responded. 

Dean Knudson, former member of the Wisconsin Elections Commission, wasn’t comfortable with Woodall’s “joking” in an election in which Biden would claim victory by about 20,000 votes.  

“I do believe she was joking, but to joke about this displays an extraordinary level of insensitivity and callous disregard for the damage caused by actions in Milwaukee that night,” Knudson told the Journal Sentinel at the time. 

Woodall didn’t help her case when she “briefly misplaced a flash drive containing vote counts on Election Night.” A police officer later had to deliver the data collection device. Woodall told left-leaning publication Wisconsin Watch that the flash drive was “never left unattended and that the staff had remained in the room throughout the process.” 

In another piece hailing the moral fortitude and election integrity of Milwaukee’s embattled elections chief, the same publication quoted Woodall, who couldn’t resist taking a shot at then-President Donald Trump. The Republican and millions of his fellow Americans didn’t find Wisconsin’s handling of the 2020 election as unimpeachable as Woodall and her friends in the accomplice media did. 

“(It’s been) extremely partisan and divided,” she told Wisconsin Watch. “The fact that people are supporting someone trying to overturn the actual results is disappointing.” 

Meet the New Boss… 

Mayor Cavalier Johnson, who served as president of the Milwaukee Common Council at the time, joined a long line of Democrats praising Woodall’s performance during the 2020 election, describing it as “stellar.”

It would appear Johnson’s estimation of Woodall has changed somewhat since then, but his spokesman claims the mayor had “no issues with the quality or integrity” of her work. 

“The Mayor has expressed full confidence in Ms. Gutierrez saying she is ideally suited to this position. He has made it clear, the department will have the resources it needs to fulfill its duties,” Fleming said. 

Johnson told WISN, an ABC News affiliate in Milwaukee, that Gutierrez “will lead the office at an important juncture when public scrutiny of the work of the department will be extremely high.” 

“I have confidence in her, and I will make certain the department has the resources it needs to fulfill its duties,” the mayor added. 

But will Gutierrez be more hostile to election integrity than Woodall was criticized for being? Will she be more pliant on massaging election law and working with partisan “nonpartisan” groups than her former boss? Wisconsin conservatives are worried, and rightly so. 

Johnson and his staff colluded with Democrat Party operatives in a sweeping get-out-the-vote campaign, Empower Wisconsin reported a month before the 2022 election. Text messages showed as much. 

The communications, obtained by State Rep. Janel Brandtjen (R-Menomonee Falls) showed longtime Democrat Party operative Sachin Chheda telling Johnson and his staff what to say about the Wisconsin Votes 2022 get-out-the-vote campaign. The effort was funded by a left-wing activist group with close ties to the Center for Tech and Civic Life.

Perhaps Woodall wasn’t playing as nice with the leftist groups looking to grab another election for Biden and fellow Dems. 

Bob Spindell, one of three Republicans on the six-member Wisconsin Elections Commission, said controversy has long surrounded Woodall, who is named in several election integrity complaints.  

“She’s tried to ease some of the complaints of some of the Republicans,” Spindell, marked as an “election denier” by Democrats and corporate media for questioning the handling of the 2020 election in places like Milwaukee and Madison, told me. “She has been under the gun for a lot of things.” 

Things were rocky for Woodall before she ascended to the leadership post. In late June 2020, then-Mayor Tom Barrett tapped Woodall for the executive director role following the retirement of her longtime predecessor. The Common Council delayed her appointment over “equity” agenda blustering as Black Lives Matter riots were sweeping the nation. 

As the Journal Sentinel noted, the delay came about four months before the election — and in Milwaukee, which was “expected to play a key role determining whether President Donald Trump wins reelection.” Wisconsin’s biggest city faced “being left with no one running its elections agency.” 

Four years later, Woodall is out, and the same spotlight is on Milwaukee in the sequel to the 2020 election. 

Knodl says Johnson has some explaining to do. Is he glad to see Woodall gone? 

“That all hinges on the new person and the motivation of the mayor,” he said. “On one hand, I’d say yes. She was suspect in her handling of the Milwaukee elections department. On the other hand, who knows what the mayor’s motivations are.” 

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