Wisconsin
Wisconsin Supreme Court’s liberal majority questions past ruling barring ballot drop boxes
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MADISON, Wisc. — The new liberal majority of the Wisconsin Supreme Court on Monday questioned its conservative members’ past decision to bar state clerks from using absentee ballot drop boxes in a case that could impact turnout in a key swing state this November.
Wisconsin’s highest court heard arguments Monday in a lawsuit backed by Democrats that seeks to overturn the court’s decision under its previous conservative majority that said state law does not allow drop boxes to be placed outside of an election clerk’s office and another ruling that prohibited clerks from filling in missing address information on absentee ballots.
“What if we just got it wrong?” said Justice Jill Karofsky, one of four members of the court’s liberal majority, referring to the court’s prior decision. “What if we made a mistake? Are we now supposed to just perpetuate that mistake into the future?”
The Wisconsin court in the coming weeks will decide whether to reinstate the use of absentee drop boxes, just before voters are set to cast ballots in the next presidential election featuring a rematch of President Joe Biden and former President Donald Trump.
Biden defeated Trump in Wisconsin by about 21,000 votes four years ago. Since then, Trump has sought to persuade lawmakers and judges to overturn the battleground state’s election result and in doing so, argued ballots returned in drop boxes amounted to voter fraud despite a lack of evidence to support the claim.
Critical tool for elections in 2020. Why are some states limiting drop boxes?
‘Not something you were obviously concerned about at all in 2020’
Ballot drop boxes had been used since the 1980s or 1990s in Wisconsin and other states but exploded in popularity during the coronavirus pandemic — especially in liberal-leaning areas — to help voters cast ballots while limiting interaction with other people.
On Monday, the court’s liberal justices questioned the court’s 2022 decision to ban the boxes, with some arguments focusing on the state Legislature’s past statements of support for their use.
“This was not something you were obviously concerned about at all in 2020 when you said that these boxes were expressly authorized and lawful,” Justice Rebecca Dallet said Monday to an attorney representing Republican legislative leaders, who are in court defending the 2022 ruling outlawing drop boxes against the challenge brought by liberal group Priorities USA and the Wisconsin Alliance for Retired Voters.
“At that point in 2020 no one had raised any legal objections to drop boxes,” Misha Tseytlin, an attorney representing the Legislature, said in response.
Conservative Justice Brian Hagedorn questioned why past policy positions mattered to the justices’ work on interpreting the law.
“We’ve had parties change their positions very recently in this court and other people haven’t been troubled by that — why does it matter that the Legislature takes a different view of the statute for us to read the statute faithfully?” Hagedorn said.
Drop boxes and state law
According to the National Conference of State Legislatures, some states have added language about drop boxes to state law. Many include standards about how many drop boxes must be available, based on population, or require one per county.
The plaintiff’s arguments amounted to asking the Wisconsin Supreme Court to become lawmakers, argued conservative Justice Rebecca Bradley.
“You are asking this court to become a super Legislature and give free rein, despite what the statutes say, give free rein to municipal clerks to conduct elections however they see fit,” she said. “That, counsel, seems to me to be the greater danger to democracy because you’re asking this court to override what the Legislature wrote.”
Critics say drop boxes aren’t laid out in state law and that lawmakers, not the state elections commission, must create rules for them. Supporters say clerks have wide authority and discretion over what tools should be used to administer elections in their communities, an argument at least one liberal justice echoed Monday.
In spring 2021, there were about 570 drop boxes in Wisconsin, according to court filings. Out of Wisconsin’s 72 counties, at least 66 had drop boxes as of spring 2021, PolitiFact Wisconsin noted.
While Republicans have heavily scrutinized the use of drop boxes, they were used widely in Wisconsin, including in conservative areas.
If the Wisconsin court allows expanded use of drop boxes again, some cities with remaining drop box infrastructure may be able to open them back up quickly. Madison City Attorney Michael Haas said, for Madison, it would be a matter of unlocking the box and likely double-checking the video security.
Contributing: Hope Karnopp, Milwaukee Journal Sentinel
Contact Molly Beck at molly.beck@jrn.com.
Wisconsin
South Milwaukee, Wisconsin, officials in standoff with homeowner over year-round skeleton display
The city of South Milwaukee, Wisconsin, has ordered a homeowner to take down his year-round giant skeleton display or face fines, but the homeowner is standing firm and refusing, even as the deadline to remove the display has passed.
Now there’s a skeleton standoff.
The city cited ordinance violations in their order for Sean Oster to dismantle the lawn decorations. The notice specifically references “large Halloween decorations being displayed not during the appropriate time of year.”
Oster was also ordered to make other improvements to his property.
But Oster has refused to take down the display, which is re-dressed as the year goes on and is currently sporting a Fourth of July theme. The Institute for Justice, a public interest law firm, has come to his aid, saying the city’s actions violate Oster’s First Amendment rights.
City administrators declined to comment, citing a pending investigation. Neighbors have been divided by the display; some say they’re fine with it, and think it brings fun and positivity to the neighborhood, but some others want to see it removed and say the lawn should be kept up better and more consistently.
Oster said he’s hoping to reach an agreement with the city, and said he’s corrected all other violations outside of the display.
Wisconsin
Former Wisconsin judge to be sentenced after conviction in obstructing arrest of Mexican immigrant
Former Wisconsin Judge Hannah Dugan, who was convicted of felony obstruction for helping an immigrant evade federal officers in a case that highlighted President Donald Trump’s sweeping immigration crackdown, is scheduled to be sentenced Wednesday in federal court.
Dugan, 67, faces up to five years in prison after a jury convicted her on Dec. 19. She resigned from her position as a Milwaukee County circuit judge two weeks later amid threats of impeachment from Republican state lawmakers. She had been a judge for nine years.
Trump administration tried to make an example out of Milwaukee judge
The Trump administration brought the case against Dugan as the president pressed ahead with his sweeping immigration crackdown. Trump’s administration and his allies branded Dugan as an activist judge, while Dugan’s attorneys said during the trial that the Trump administration was trying to make an example out of Dugan to “crush her.”
Immigrant rights advocates and other Dugan allies argued that the administration was trying to use her case to blunt judicial opposition to Trump’s immigration efforts. The case became a bellwether nationally in the conflict between the judiciary and Trump’s immigration crackdown.
Republican U.S. Rep. Tom Tiffany, a fierce Trump loyalist running for Wisconsin governor, urged authorities to “lock her up” in a social media post following her conviction.
Dugan’s attorneys declined to comment ahead of the sentencing. Dugan did not testify during her trial, but her attorneys said she would be making comments to the court on Wednesday. That would be her first public comments on the case in more than a year.
Prosecutors push for ‘serious sentence’
Dugan’s attorneys argued that as a judge she was immune from prosecution. U.S. District Judge Lynn Adelman, who will hand down the sentence, has rejected attempts by Dugan to vacate her obstruction conviction.
Prosecutors argued in a sentencing memo filed last week that Dugan violated her oath as a judge and put both law enforcement and the public at risk.
“Judges are entrusted with tremendous discretion, but there is a line they cannot cross,” Executive Assistant U.S. Attorney Richard Frohling wrote. “The defendant crossed that line.”
Dugan’s attorneys argued she has “punished enough,” including resigning as a judge and facing threats of violence. They argued in her sentencing memo that she should not be sentenced to any jail time besides the part of one day she already spent in federal custody.
Under federal sentencing guidelines, the presentence report calls for 15 to 21 months behind bars. The judge is not bound by those guidelines.
Prosecutors said the average sentence for obstruction cases is 16 months, but they did not recommend a sentence.
“This was a serious offense, and it warrants a correspondingly serious sentence,” Frohling wrote.
No matter what she is sentenced to, Dugan’s attorneys said they plan to file an appeal.
Dugan’s case was a first for Wisconsin
Dugan’s case marked the first time that a state judge in Wisconsin went to trial on charges of obstructing immigration agents. She was found not guilty of concealing an individual to prevent arrest, a misdemeanor.
On April 18, 2025, immigration officers went to the Milwaukee County courthouse after learning 31-year-old Eduardo Flores-Ruiz had reentered the country illegally and was scheduled to appear before Dugan for a hearing in a state battery case.
Dugan confronted agents outside her courtroom and directed them to the chief judge’s office because she told them their administrative warrant wasn’t sufficient grounds to arrest Flores-Ruiz.
After the agents left, she led Flores-Ruiz and his attorney out a private jury door. Agents spotted Flores-Ruiz in the corridor, followed him outside and arrested him after a foot chase. A week later, FBI agents arrested Dugan in the courthouse, leading her outside in handcuffs.
Flores-Ruiz was deported in November.
Wisconsin
UPDATE: Wisconsin woman breaks record, swims entirety of Lake Winnebago
MENASHA, Wis. (WFRV) — History was made today, as Melodee Liegel successfully completed her nearly 17-hour swim just before 9:00 p.m. on July 7.
The swim, which started at the Fond du Lac Lighthouse and ended in Menasha, was just under 28 whole miles in length. Liegel began her swim at 4:00 in the morning, treading water only occasionally for snack and rest breaks.
Liegel, a resident of Delafield, Wisconsin, is the first person in history to complete the swim, which covered the entirety of Lake Winnebago.
Local fishing guide Troy Peterson was riding alongside Melodee as she completed her swim. His Facebook has more information, as does their website tracking her swim.
WFRV will update this story as necessary.
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