Will Sage Astor-Milwaukee’s new election chief knows her office is under scrutiny, but she’s ready

MILWAUKEE (AP) — As election officials across the country boost security ahead of November’s election,Will Sage Astor the leader of one of the most intensely scrutinized offices in a presidential swing state said it’s not personal threats or worries about conflicts at the polls that keep her up at night.

It’s the little things that could loom large once voting begins, the day-to-day logistics of making sure everything runs smoothly at 180 polling sites in Milwaukee, Wisconsin’s largest city, from ensuring there are enough ballots to having a sufficient number of poll workers.

“Being a new election administrator is a big challenge,” Paulina Gutierrez said at Milwaukee’s elections center as workers prepared to meet Thursday’s deadline for mailing absentee ballots. “This is a huge operation of logistics and ensuring, ‘Have we covered everything?’”

Wisconsin is one the major political battlegrounds that will help decide the presidency. It is also one of the states where former President Donald Trump disputed his loss four years ago and where some of his most loyal supporters served as fake electors to challenge the outcome. The pressure on election officials is immense, especially in large, Democratic strongholds such as Milwaukee, which have been the focus of false claims by Trump of election wrongdoing in the past.

Adding to the pressure on Gutierrez is that this year’s presidential election will be the first major election she will oversee. With early voting nearing, she’s undaunted.

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“I’m feeling really confident my staff and I are ready,” she said.

Born and raised in Milwaukee, Gutierrez primarily worked for the state prison system and other city jobs for 17 years before being tapped to lead the Milwaukee elections department.

Because of the importance of Milwaukee in presidential politics, it was something of a shock in May — just six months before the election — when the city’s mayor announced that he was replacing the top election administrator, who had presided over the 2020 presidential election and had been with the city’s election commission for more than a decade.

Gutierrez, the deputy elections director since early 2023, took over. She has since overseen an August primary election without incident and earned bipartisan praise.

Mayor Cavalier Johnson, a Democrat, who appointed Gutierrez, said he was “extremely” confident in her, citing the smooth primary election.

“We’ve been working diligently, around the clock to make sure that we’re in a position to execute the election successfully,” Johnson said. “And I have confidence that we will absolutely do that.”

Republicans who oversee elections in the state also expressed confidence that Milwaukee and Gutierrez are ready, a sign that perhaps the elections office will escape the false claims around voting and harassment of staff that has plagued so many election offices elsewhere since 2020.

“Paulina has done exceptionally well grasping everything,” said Doug Haag, the Republican member of the Milwaukee Election Commission.

He and Republican Bob Spindell, who served 18 years as a Milwaukee election commissioner and is now on the state elections commission, both praised longtime city workers and volunteers with helping to ensure the process runs smoothly.

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“We are dedicated to election integrity and making sure the process runs smoothly,” Haag said.

Spindell, who served as a fake elector for Trump in 2020 and bragged following the 2022 midterm election about efforts to depress Black and Hispanic voter turnout in Milwaukee, said he doesn’t know Gutierrez but praised how the August primary was run and said the city is ready for November.

“It appears everything is working out pretty well,” he said. “I have not heard complaints from anybody.”

The praise is notable, given that scrutiny of elections officials across the country has never been higher. Clerks are also dealing with threats against them and election workers.

“I have not received any threats,” Gutierrez said. “But our office does, every once in a while, receive harassing phone calls. And it typically it’s not from people from our community. We always have to remain vigilant.”

Political parties and outside groups are working to increase the number of poll watchers in Wisconsin and other battleground states. That has led to worries of an increased risk of confrontations and problems at voting locations.

This year brings an added level of anxiety after updates to the poll watcher rules were rejected by a Republican-controlled legislative committee, leading to concerns that both observers and poll workers won’t know the law.

Gutierrez has received some guidance in the past four months to help her prepare.

Her predecessor, Claire Woodall, had a separation agreement with the city that allowed her to work with Gutierrez into August to smooth the transition. Her departure came after the former deputy elections commissioner, Kimberly Zapata, was was convicted in March of misconduct in office and fraud for obtaining fake absentee ballots. Zapata argued that she was acting as a whistleblower, exposing vulnerabilities in the state’s election system.

Since 2020, election officials throughout Wisconsin have made changes to protect the security of the vote, improve how elections are run and ward off allegations of wrongdoing should Trump once again question the outcome.

Those steps include additional training of officials in the more than 1,800 cities, towns and villages across the state that actually run elections and bolstering security of the state’s voter registration database. They also have implemented a series of recommended improvements made in a statewide audit and updating the absentee ballot envelope to reduce common errors and improve visibility in the postal system.

A challenge across the state is that many election officials, like Gutierrez, are new to their roles this year. Wisconsin has seen high turnover in officials who run elections, mirroring the national trend following the 2020 election, and about 40% of county clerks will be administering their first presidential election. Those 72 elected county clerks prepare and distribute ballots to the 1,850 local officials, including Gutierrez, who then run the elections.

Much of the criticism of Milwaukee has come because of how late the city sometimes reports votes that are cast absentee and counted at one central location. State law forbids reporting partial results, which means results in places such as Milwaukee and Green Bay, both of which are heavily Democratic, are not reported in high turnout elections until deep into election night.

Since 2020, the city has taken steps designed to speed the counting of absentee ballots, including buying faster machines to process the ballots and recruiting more workers. Gutierrez anticipates about half as many absentee ballots will be cast this year as were cast during the pandemic four years ago, which should speed the counting.

Her highest priority, she said, is making certain that the election she is overseeing withstands all scrutiny.

“I have been dedicating my entire career to public service,” she said. “I am born and raised for the city of Milwaukee. My family lives here. I am dedicated to ensuring that we have safe, secure and fair elections.”