Arrest of Milwaukee judge echoes Massachusetts case — with one key difference

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Milwaukee County Circuit Court Judge Hannah Dugan was arrested on Friday for allegedly helping a man living in the United States without legal status evade federal immigration authorities. Dugan faces two federal felony counts — obstruction and concealing an individual.
Dugan’s case is similar to a 2019 case brought by federal prosecutors against Massachusetts Judge Shelley M. Richmond Joseph. In that case, Joseph was accused of helping an unauthorized immigrant avoid an Immigration and Customs Enforcement agent after a court appearance.
In both cases, federal officials alleged the state judges allowed the defendants to exit their courtrooms through alternative routes to avoid federal immigration officials waiting outside the courtrooms in publicly accessible areas.
In a criminal complaint filed last week, federal officials alleged that Dugan confronted immigration enforcement officials outside of her courtroom as they waited for a defendant who was scheduled to appear before her finished his court business. Witnesses reported that Dugan “was visibly upset and had a confrontational, angry demeanor,” according to the complaint. Dugan asked to see the warrant the immigration officials were acting upon and then referred them to see the county’s chief judge.
After returning to the courtroom, Dugan then escorted the man and his attorney through a door that leads to a “nonpublic area” of the courthouse, the complaint states.
A similar series of events unfolded in the Massachusetts case. After learning that an ICE agent was waiting to arrest a defendant, Joseph eventually had the man exit the courtroom through a nonpublic exit, federal authorities alleged in a 2019 indictment. A separate court official then helped him exit the building through a back door.
The Massachusetts case was dismissed in 2022. In exchange, Joseph referred herself to the Massachusetts Commission on Judicial Conduct, per The New York Times.
One key difference between the two cases: Joseph was indicted. Dugan was served a criminal complaint. To secure an indictment, prosecutors have to present evidence to a panel of everyday Wisconsin residents and convince them there is probable cause a crime has been committed. For criminal complaints, officials only have to get the sign-off of a federal judge, but then later have to secure an indictment from a grand jury, two former federal prosecutors told Wisconsin Watch.
Now, the federal government has 21 days to seek an indictment, according to Laurie Levenson, a law professor at Loyola Marymount University and a former federal prosecutor.
“It is unusual that this happened with an arrest and complaint because there really is no indication that the Judge was a flight risk or danger to the community,” she told Wisconsin Watch in an email. “They easily could have gone to the grand jury first and summoned her in IF the grand jury wanted to indict.”
Stephen Kravit, a Milwaukee area attorney and former federal prosecutor, said criminal complaints are rare in the Eastern District of Wisconsin and are usually reserved for “an exigent situation where the defendant’s whereabouts aren’t specifically known or the presence in this area is temporary.”
“None of that applies to a sitting Circuit Court Judge,” he added in an email.
Instead, Kravit said, “this was done in a hurry to make a political point.” He added, “Normally, a person charged even with felonies aged 60+ with no record and no chance of fleeing would be summoned to show up at an appointed time for booking and arraignment. Not here. And that was the point.”
🚘 Budget road trip. The Joint Finance Committee will hold a pair of hearings on Monday and Tuesday this week, stepping away from the Capitol in Madison to hear from Wisconsin residents in Hayward and Wausau about what they want included in the state’s next two-year budget.
It will be the third and fourth time so far that the committee has heard from the public on the spending plan. But as the GOP-controlled committee continues to go through the motions of crafting the budget, Assembly Speaker Robin Vos, R-Rochester, indicated last week that Republican lawmakers could punt on passing a new budget altogether.
Vos was reacting to a Wisconsin Supreme Court decision that left intact a move from Gov. Tony Evers that provided for annual public school funding increases for the next 400 years. “It’s certainly a possibility if we can’t find a way for us to get to a common middle ground,” Vos said of spiking the funding plan last week on the “Jay Weber Show.” “But that’s not the goal.”
“It’s something we’re talking about, but it wouldn’t be the first go-to,” Vos added, noting that it has never happened before. The state has passed a budget every two years since 1931, according to the nonpartisan Legislative Reference Bureau.
But even if the Legislature were to pass on sending a new spending plan to Evers, things in the state wouldn’t shut down. In Wisconsin, the state continues operating at the existing spending levels until a new budget is approved.
📈 Student homelessness rising. Homelessness among K-12 Wisconsin students reached a new high in 2024, increasing 9% over the previous year despite total enrollment declining slightly.
That’s according to a new report from the Wisconsin Policy Forum, which found that a little more than 20,000 Wisconsin students were homeless in 2023-24. If that figure seems high, it’s because it is. Homelessness among students is counted using a definition that is more expansive than the one employed by the U.S. Department of Housing and Urban Development. The federal McKinney-Vento Act defines homeless children and youth as those “who lack a fixed, regular, and adequate nighttime residence.”
It’s the third straight year that student homelessness increased in Wisconsin, the report found, reaching a new high since the state Department of Public Instruction started keeping data in 2019.
“The number of students affected by homelessness has grown and is likely to continue to remain high in the near future as an insufficient supply of affordable housing remains a lingering problem throughout the state,” the report concludes. “Addressing the needs of this high-risk group of students could benefit not only them but also Wisconsin’s educational outcomes overall.”
Wisconsin Watch’s Hallie Claflin has been documenting the state’s rural homelessness crisis, including in her latest report about police departments transporting homeless people outside their jurisdiction. We’ll be watching the budget process closely to see if lawmakers address this issue or similarly treat it as out of sight, out of mind.
Arrest of Milwaukee judge echoes Massachusetts case — with one key difference is a post from Wisconsin Watch, a non-profit investigative news site covering Wisconsin since 2009. Please consider making a contribution to support our journalism.