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On Immigration, Wisconsin and Hannah Dugan

May 1, 2025 By Debbie Young

By Oleg Kozlovskiy @Adobe Stock

Hannah Dugan is the Milwaukee judge arrested for helping a man evade immigration authorities. On Tuesday, the Wisconsin Supreme Court suspended Dugan, reports NRO, arguing that it is in the public interest to relieve her of her duties as she faces two federal charges.

The Background

An immigration official had issued an arrest warrant for Flores-Ruiz, who was in the U.S. illegally and a serial immigration-law offender. ICE deportation agents planned to arrest him at the courthouse. ICE sometimes seeks to arrest illegal migrants in the public areas of courthouses because that’s where they can locate migrants accused of crimes. It is often safer than home arrest because the migrant will have had to go through a security checkpoint.

According to a two-page order, the court declared it was acting to protect public confidence in Wisconsin courts during the criminal proceedings against Dugan. The order noted that the court was acting on its own initiative and was not responding to a request from anyone. Liberal justices control the court 4-3.

Is it a surprise that legal judges aren’t defending one of their cohorts? Jim Geraghty views it as an indication that some judges in the state see her alleged actions as the sort of thing that shakes the public’s confidence in the objectivity and prudence of the judicial branch.

Dugan is assembling an all-star team of lawyers for her defense:

  • Leading Dugan’s legal team is Steven Biskupic, the former U.S. attorney in the Eastern District of Wisconsin from 2002 to 2009. Republican President George W. Bush selected Biskupic, who oversaw a series of public high-profile corruption and police misconduct cases, including the convictions of seven Milwaukee police officers in the beating of Frank Jude, Jr. Biskupic was a career prosecutor before his term as U.S. attorney. He is now in private practice.
  • Another prominent member, former U.S. Solicitor General Paul Clement, is a Cedarburg native. As solicitor general from 2005 to 2008, Clement argued more than 100 cases before the U.S. Supreme Court. Clement, a conservative who was appointed by former Republican President George W. Bush, currently represents the law firm WilmerHale, which is suing the Trump administration after it was targeted by an executive order. Clement has been dubbed by some “the LeBron James of lawyers.”

Clement, according to Mr. Geraghty, is as talented a litigator as there is in the legal world.

The alien, according to NRO’s Andrew McCarthy, is a Mexican named Eduardo Flores-Ruiz, who is illegally in the United States yet again after having been deported a dozen years ago — making him not just automatically removable but liable to felony prosecution. (Contrary to what transnational progressives claim, it is a crime to enter the United States illegally, but the crime is a misdemeanor; reentry after removal, however, is a felony, and the penalty can be severe depending on the alien’s criminal record.)

Why was Flores-Ruiz in Judge Dugan’s court? He was facing three criminal charges of battery, domestic abuse, and infliction of physical pain or injury. The proceeding in state criminal court on April 18 was a pretrial conference at which his alleged victims were present.

In a sensible world, explains Mr. McCarthy, (1) Flores-Ruiz would have been detained pretrial on the state domestic battery charges, given the abundant evidence that he was both a danger to the community and a flight risk. (2), a federal detainer would have been lodged with the state corrections department so that federal agents would be notified to take custody of him the moment his state prosecution and any sentence were concluded.

Milwaukee is a state hostile to immigration reform, even if it hasn’t formally enacted “sanctuary” ordinances.

When an arrest is made, the city does not inquire into an arrestee’s immigration status. And its corrections department neither notifies the federal Immigration and Customs Enforcement (ICE) agency in advance of an illegal alien’s release from state custody nor agrees to detain illegal aliens for a few days beyond their state incarceration terms so that ICE can get there and take them into federal custody in the safety of the state prison.

Let’s see. A Democratic-controlled city and its officials, Judge Dugan included, are the primary culprits in Flores-Ruiz’s attempted flight from federal officers who were armed with a warrant for his arrest. The obstruction prosecution of Judge Dugan will not be an easy one, thanks to the Democrats’ lawfare campaign against now-President Donald Trump, including its charges of obstruction that were zealously opposed by such Trump loyalists as now–Attorney General Pamela Bondi and the FBI’s current director, Kash Patel.

Andrew McCarthy admits that he isn’t going to say anything analogous to what he said throughout anti-Trump lawfare:

“We are not talking here about Dugan’s moral or political culpability. We are talking about whether proof beyond a reasonable doubt can be established in the criminal justice system, in which she is presumed innocent and enjoys important legal protections — including the skepticism of federal courts that criminal prosecution is an appropriate vehicle for addressing the actions of public officials within the scope of their authority.”

Mr. McCarthy worked for nearly 20 years as a federal prosecutor, as well as for several years at the U.S. Marshals Service in court and witness security.

Federal agents decided to use the opportunity presented by Flores-Ruiz’s court appearance in connection with state criminal charges to arrest him federally. It appears that, in response to sanctuary policies, the feds have begun to make a practice of this at the Milwaukee state courthouse. This is the third time such furtive operations have caused a public disturbance.

The real problem here, advises Mr. McCarthy, is Democratic sanctuary policies. Not to be overlooked are the reasons that blue cities and states are able to refuse to cooperate with federal immigration enforcement.

At the time of our country’s founding, the states had principal authority over who was permitted in their territories. The federal role in immigration enforcement was dubious.

  • Over several decades, federal courts gradually teased a federal role out of Congress’s constitutional responsibility for naturalization terms and the national government’s duty to secure the borders. Inexorably, once the federal courts discovered a federal role, they enabled federal power to swallow state power — to the point that, during the Obama and Biden administrations, federal courts allowed red states that wanted to support Congress’s immigration laws to be straitjacketed by executive nonenforcement policies.
  • Second, the feds haven’t quite extinguished state sovereignty. The law is that, while the states may not obstruct federal law enforcement, the feds may not commandeer state resources to enforce federal law.

Where does the refusal to be commandeered cross into obstruction? McCarthy asks that you trust him when he tells us that the federal agents who planned to arrest Flores-Ruiz in the state courthouse would never have done the same thing in a federal courthouse.

They didn’t tell Judge Dugan or the chief judge of the court that they were coming. They didn’t alert court security personnel or the local police. In the federal system, agents of the executive branch would have understood that they did not have carte blanche to conduct enforcement operations in a federal courthouse — the judiciary’s turf.

They would not conduct a planned, non-exigent arrest in a courthouse without first ensuring that they had the cooperation of the chief judge, any judge whose cases might be affected, and the court security personnel. The Justice Department would grasp that if the federal judiciary believed that law enforcement agents of the executive branch were exploiting the courts’ administration of justice, it would not go well for the DOJ in the many law enforcement initiatives — search warrants, wiretaps, grand juries, trials, etc. — for which they need the federal judiciary’s assistance.

Because of federalism principles, federal law enforcement agencies should arguably be more solicitous of state courts and state law enforcement. At a minimum, they should show the state respect equal to what they show federal counterparts.

The federal agents did not have access to the nonpublic area that Dugan used to help Flores-Ruiz try to evade arrest.

“… while the federal agents had an administrative arrest warrant, they did not seek a search warrant from a federal judge permitting them to make an arrest anyplace on the grounds of the state courthouse. As the complaint details, the state judges were upset that the federal agents did not have a warrant issued by a federal court. Clearly, if the agents had asked, a federal judge — more sensitive to interstate comity with state courts than the Trump administration’s agents were — might well have said no.”

Even in a federal courtroom, there can be a violent confrontation. A courthouse is not just any ol’ building with a common area open to the public. Don’t forget, the potential of violent confrontations in a courthouse is disruptive to the state’s administration of justice, McCarthy reminds readers.

State courts are not police departments. The judicial department, whether state or federal, strives to present itself as a fair arbiter between law enforcement and accused criminals; it does not want to be seen as an instrument of law enforcement.

McCarthy asks readers to remember what President Trump’s defense was when he was charged with obstruction and other offenses by Biden DOJ special counsel Jack Smith.

(Trump) claimed immunity from prosecution because the actions at the heart of Smith’s indictment — the unsubstantiated public allegations of election fraud, the attempt to browbeat the Justice Department into supporting those allegations, the provocative speech on the Ellipse, the failure to take timely action to ask the Capitol rioters to stand down — were all taken while Trump was president. His lawyers argued that, even if those actions appeared unseemly, none of them was illegal per se, and all were within the scope of his broad executive power.

Donald Trump’s defense was successful to the point that Trump’s highly political Justice Department is trying to rewrite history to say that the real abuse of power was Smith’s prosecution, not Trump’s actions (notwithstanding that he was impeached by the House and that the Senate vote against him was 57–43 — lopsided, though short of the two-thirds needed for conviction).

That’s the defense Judge Dugan is going to use, promises McCarthy, … that Dugan was acting within the scope of her legal duties.

… it is not illegal per se to allow a defendant and his counsel to leave the courtroom by a limited-access route, and her actions were consistent with her judgment regarding the proper administration of the state judicial system, which the federal agents — ignoring principles of federalism — were disturbing with their covert arrest operation. She will say she was not hiding Flores-Ruiz; as a city official, by allowing an illegal alien to leave a state facility, she was declining to be commandeered into assisting federal authorities in enforcing federal immigration law, just as the Milwaukee corrections department does, consistent with the city’s sanctuary policies.

Andrew McCarthy is not sure Dugan’s defense will work. He is sure, however, that “it won’t get laughed out of court by a Milwaukee jury.”

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Debbie Young
Debbie Young
Debbie, our chief political writer of Richardcyoung.com, is also our chief domestic affairs writer, a contributing writer on Eastern Europe and Paris and Burgundy, France. She has been associate editor of Dick Young’s investment strategy reports for over five decades. Debbie lives in Key West, Florida, and Newport, Rhode Island, and travels extensively in Paris and Burgundy, France, cooking on her AGA Cooker, driving through Vermont and Maine, and practicing yoga. Debbie has completed the 200-hour Krama Yoga teacher training program taught by Master Instructor Ruslan Kleytman. Debbie is a strong supporting member of the NRA.
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