The cases of Milwaukee County Judge Hannah Dugan and Massachusetts Judge Shelley Joseph represent a modern chapter in America’s oldest constitutional tension: federal enforcement power versus state judicial autonomy.

In 2018, during the Trump administration, Judge Joseph was charged with conspiracy and obstruction for allegedly helping an undocumented immigrant exit through her courthouse’s back door to avoid ICE agents. After a year-long investigation and her suspension without pay, the case dragged on for years. When the Biden administration took office, federal prosecutors ultimately dropped the charges, transferring the matter to the Massachusetts Judicial Conduct Commission.

Fast forward to 2025, and Judge Dugan faces similar charges after allegedly directing a defendant and attorney through an alternate courthouse exit. Unlike Joseph’s case, Dugan was swiftly arrested in her courthouse – handcuffed and photographed – a deliberate spectacle meant to send a message rather than simply enforce the law.

Before 2018, the notion of federal agents slapping cuffs on a state judge for courtroom decisions belonged to fiction, not American legal reality. Then, during Trump’s first term, Judge Joseph faced charges. Now, seven years later, Judge Dugan stares down the same prosecutorial barrel. Two cases, two Trump administrations, two unprecedented intrusions into a domain once considered sacrosanct. The historical ledger speaks its stark truth: in over two centuries of American jurisprudence, these prosecutions exist as lonely anomalies, curious artifacts of an era where the boundaries between federal power and judicial independence found themselves suddenly, dramatically redrawn.

How Judge Dugan’s Legal Team Will Argue Against the Charges

Judge Dugan’s legal team is likely mounting a defense based on judicial immunity, arguing that her actions were official judicial acts for which she cannot be prosecuted. They cite Supreme Court precedent on judicial immunity and have referenced the Trump immunity case to support their position that such immunity is an absolute bar to prosecution at the outset, not merely a defense at trial. They also argue that ICE’s administrative warrant did not compel her cooperation, that her conduct did not amount to obstruction or concealment under federal law, and that the defendant was arrested in public shortly after leaving her courtroom, undermining claims of intentional evasion. The defense further frames the prosecution as an unprecedented and unconstitutional attack on judicial independence.

Potential Impact on Federal-State Judicial Relations

Both cases highlight and may intensify the ongoing conflict between aggressive federal immigration enforcement and state judicial authority. The prosecutions have been widely interpreted as attempts to intimidate judges and deter them from exercising independent authority in their courtrooms. If such prosecutions succeed or even proceed to trial, they could chill judicial discretion, making judges more hesitant to question federal agents or assert control over their courtrooms. Conversely, if the cases are dismissed or judges are vindicated, it could reaffirm the constitutional limits on federal power and strengthen state and local autonomy in the face of federal immigration priorities. Ultimately, these cases will influence how far federal agents can go in state courthouses and how boldly state judges can assert their independence in the face of federal pressure.

The Fatal “Hiding” Requirement: Why The Concealment Charge Is Doomed

The prosecution’s case against Judge Dugan collapses when examining the essential “hiding” element required under 18 U.S.C. § 1071. Court documents reveal that federal agents accompanied Flores-Ruiz and his counsel in the same elevator as they descended to street level.

As the Justice Department’s manual acknowledges, “Section 1071 does not prohibit all forms of aid to a fugitive”. Courts have consistently held that “trivial or momentary delays generally do not satisfy the statute.” When federal agents maintain visual contact the entire time and complete an arrest just minutes later, there is no concealment under any reasonable legal interpretation.

Yes, she used a different door, but that’s NOT “hiding” under federal law (18 USC §1071). Purposeful action isn’t enough; the statute requires concealing someone “to prevent discovery.”

Flores-Ruiz walked through a standard courthouse door and was arrested 22 minutes later in the public hallways. That’s not concealment-it’s simply using Door B instead of Door A in her courtroom.

“She adjourned without consulting prosecutors/witnesses” ≠ Corrupt Intent

Judge Dugan’s case represents a direct clash between a judge’s statutory authority to control her courtroom and federal agents’ enforcement tactics.

Wisconsin law explicitly grants judges like Dugan the power to “impose reasonable limitations on access” and “maintain proper decorum and appropriate atmosphere” in their courts. Judges have the absolute right to adjust their calendars unilaterally- they need not consult prosecutors before adjourning.

When ICE agents disrupted proceedings with only an administrative warrant, Judge Dugan responded by exercising this legitimate state authority, directing them to follow proper channels through the Chief Judge.

Even today, the Chief Judge still has no straightforward procedure for handling administrative versus judicial warrants from federal agencies. At the same time, judges maintain their need to conduct court proceedings without disruption in the absence of genuine emergencies.

The Anti-Commandeering Doctrine: “Refusing to Help is Not the Same as Impeding”

The Ninth Circuit Court of Appeals provided clear guidance on this tension. In United States v. California, the court upheld California’s sanctuary state law (SB 54), concluding that “any obstruction caused by SB 54 is consistent with California’s prerogatives under the Tenth Amendment and the anticommandeering rule.”

Most crucially, the Ninth Circuit established a principle directly applicable to these judicial cases: “Refusing to help is not the same as impeding.” The court warned that treating noncooperation as obstruction could enable the federal government to “commandeer state resources in violation of the 10th Amendment.” When judges like Dugan choose alternative exits for defendants or decline to assist ICE agents without judicial warrants, they are refusing to help immigration enforcement, not actively impeding it.

The Constitutional Balance: Federal Power Meets State Sovereignty and the 10th Amendment

Tenth Amendment to the U.S. Constitution:
“The powers not delegated to the United States by the Constitution, nor prohibited by it to the States, are reserved to the States respectively, or to the people.”

Judge Dugan will rely heavily on this foundational constitutional text if her case proceeds to trial. However, the legal deficiencies in the prosecution’s theory suggest dismissal during pretrial motions is likely. The facts and the law don’t support a conviction. Yet conviction doesn’t appear to be the federal government’s priority- the spectacle itself was the goal, and that’s already been achieved. Americans are now polarized and debating this case in increasingly extreme terms, with reasoned, moderate analysis emerging only occasionally amid the digital noise and partisan posturing.

The fundamental legal principle overlooked in immigration federalism debates is straightforward: the federal government lacks absolute authority to commandeer state resources for immigration enforcement. Despite claims of federal supremacy in immigration matters, the Tenth Amendment establishes clear constitutional boundaries. Federal detainers issued under 8 C.F.R. § 287.7 remain legally voluntary requests, not mandates, as established in Supreme Court jurisprudence, particularly in Arizona v. United States, 567 U.S. 387 (2012), where the Court recognized that while the federal government has significant authority over immigration, states retain sovereignty over their resources and personnel.

Illinois exemplifies this delicate constitutional balance. The Illinois TRUST Act prohibits local law enforcement from detaining individuals solely based on immigration detainers without judicial warrants, a position consistent with both the Tenth Amendment and Fourth Amendment protections. Governor Pritzker’s steadfast defense of these protections demonstrates the state’s commitment to constitutional federalism rather than obstruction. As Pritzker emphasized when defending Illinois’ policies: “We’re not preventing immigration enforcement; we’re simply requiring it meet the same constitutional standards that apply to all law enforcement.” This represents the proper constitutional equilibrium: federal authorities retain enforcement power but must exercise it within constitutional confines.

When federal immigration authorities respect these boundaries, cooperation improves. Data from Illinois jurisdictions shows higher crime reporting rates in communities where local authorities maintain clear separation from federal immigration enforcement. This historical pattern reveals that effective law enforcement thrives not through federal commandeering but through respect for the dual sovereignty system that has defined American federalism since the republic’s founding- the system judges like Dugan and Joseph seek to preserve.

Constitutional Protections and the Limits of ICE Authority

Despite claims that opposing ICE’s courthouse tactics is “un-American,” a closer examination of constitutional principles reveals the opposite. The Fourth Amendment’s protections extend to everyone within U.S. jurisdiction, regardless of immigration status- a principle affirmed repeatedly by the Supreme Court.

The distinction between administrative and judicial warrants lies at the heart of cases like Judge Dugan’s. Administrative warrants, issued by ICE itself without independent review, fundamentally differ from judicial warrants that require a neutral judge’s assessment of probable cause. In Arizona v. United States (2012), the Supreme Court emphasized that even federal immigration enforcement must respect constitutional boundaries.

This distinction is critical even for individuals who entered without inspection or have removal orders. Entry without inspection constitutes a civil violation, not a criminal offense, and doesn’t automatically grant ICE arrest authority without specific evidence of removability. Courts have increasingly rejected ICE’s reliance solely on databases to justify arrests, requiring case-by-case evidence as in Miranda-Olivares v. Clackamas County (2014).

ICE’s authority also varies significantly between public and private spaces. While agents can make arrests in public with proper probable cause, this isn’t automatic- it requires specific evidence beyond mere suspicion of undocumented status. This distinction becomes particularly crucial in courthouses, as judges must balance federal enforcement against the integrity of state judicial proceedings.

Judicial review doesn’t obstruct legitimate enforcement- it prevents potential abuses like racial profiling or detention based on flawed data. The public safety argument for aggressive courthouse enforcement also falters when considering how such tactics deter immigrant communities from reporting crimes or appearing as witnesses, ultimately undermining rather than enhancing safety.

As the Supreme Court noted in Wong Wing v. United States (1896), constitutional rights for noncitizens aren’t optional-they’re fundamental to America’s legal tradition. When judges like Dugan and Joseph assert their authority against ICE’s administrative warrants, they’re not defying America’s values but upholding them in their purest form.

Sanctuary Cities: From Fugitive Slaves to Undocumented Immigrants

This tension between federal enforcement and local autonomy sounds strikingly familiar because it is. America’s first sanctuary cities emerged in the 1850s when Northern states implemented “personal liberty laws” to combat the federally enacted Fugitive Slave Act. Just as Northern judges and officials once refused to cooperate with federal slave catchers, today’s sanctuary jurisdictions limit cooperation with ICE.

As of May 2025, thirteen states and 220 cities and counties have claimed “sanctuary” status. Major metropolitan centers, including New York City, Los Angeles, Chicago, Philadelphia, San Francisco, and San Diego, have established policies prohibiting local resources from assisting federal immigration enforcement. San Francisco proudly declares itself “a City and County of Refuge” – language that deliberately echoes ancient scriptural traditions of the sanctuary. At the same time, Chicago’s “Welcoming City Ordinance” ensures immigrants can only be detained under “minimal” circumstances.

Many of these sanctuary cities frame their position as reminiscent of abolitionist resistance, asserting that their “historical and moral tradition” is “rooted in the provision of sanctuary to persecuted people.” The legal justification remains remarkably consistent across centuries: federal authorities cannot commandeer state and local resources.

The historical parallels between Illinois’ resistance to federal overreach span generations with remarkable specificity. In 1850, the Chicago City Council passed a landmark resolution declaring the Fugitive Slave Act “unconstitutional” and “cruel and unjust,” formally stating that “the city and its officers would not enforce it.” Black Chicagoans organized their community patrols to watch for slave catchers, while white allies offered sanctuary in places like the “Abolition Church.”

Today’s resistance mirrors these actions with striking similarity. Governor Pritzker’s declaration that “Illinois stands as a firewall against Donald Trump’s attacks on our immigrant communities” echoes that 1850 council resolution. The 2017 TRUST Act, which prohibits local authorities from assisting ICE with civil immigration enforcement, functions almost identically to Chicago’s 1850 refusal to help federal slave catchers. Even the language remains consistent- both eras feature Illinois officials explicitly declaring they “will not cooperate” with federal enforcement they consider unjust. When Secretary Noem recently demanded Illinois abandon these protections, calling them “disastrous” and “unconstitutional,” Pritzker’s administration responded by reaffirming the same constitutional principle that Northern states asserted against the Fugitive Slave Act: federal authorities cannot commandeer local resources to enforce policies that violate a state’s moral and constitutional principles.

Former Federal Judge Gertner’s Insight

Former federal judge Nancy Gertner incisively frames this tension:

“I think that Joseph was the canary in the coal mine. It was an early sign of what she sees as a pattern of federal overreach worsening.

This is a federal government that does not understand that there are two authorities: the state and the federal government. The federal government cannot intimidate or command state proceedings to accomplish its will.

Whatever a judge does within the four corners of her courtroom is her domain. If ICE wants to wait for people outside the courthouse, that’s fine. But do they have to be hovering inside? Do they have to arrest a witness or defendant in the middle of a trial? The answer is no. The republic will still stand if ICE respects the state bench and procedures.”

The Spectacle of Enforcement in the Digital Age

What distinguishes today’s federalism conflicts from historical precedents is their visibility. When Judge Dugan was arrested in her courthouse, the images spread instantly across social media. This visual spectacle transforms legal questions into emotional flashpoints, eliminating nuance in favor of polarization.

What crosses a judge’s mind in that crystalline moment when federal power collides with judicial autonomy? The click of metal on wrists that moments before had wielded a gavel with authority; the flashbulbs capturing her perp walk through her courthouse; the knowledge that her face would be splashed across X as either traitor or patriot before sundown. This isn’t abstract constitutional theory – it’s the soul of America wrestling with itself in real-time, with Dugan’s body and career as the battleground. These rebels in robes – Dugan and Joseph – stand as the latest incarnations of America’s oldest tension, their human faces now emblazoned across our digital consciousness, forcing us to confront what it means when a judge decides to roll the dice on her career, her freedom, for a principle most Americans couldn’t name.

Beneath these clinical facts pulses the raw human drama of Judge Dugan’s experience – a lifetime on the bench advocating for the underdog, for compassion within justice, suddenly finding herself cast as either villain or hero in America’s endless immigration theater. That instant in her chambers when she realized federal agents were waiting like predators in her courthouse corridors – what cold electricity must have shot through her judicial spine? The sacred sovereignty of her courtroom, built through decades of careful rulings and measured justice, was suddenly invaded by outside force.

The portrait painted by her detractors-arrogant, imperious, a black-robed tyrant drunk on power who thought she’d outfox the feds and wink a criminal alien to freedom-crumbles when held against the flesh-and-blood reality. They can’t taste the copper tang of fear that must have flooded her mouth when those agents appeared in her domain without warning, protocol, or the Milwaukee courts having established any clear policy on how judges should handle these federal incursions. Those who’d paint her as some radical resister miss the point entirely. This wasn’t a revolution; this was reflex- the instinctive protection of judicial independence bred into American judges since Marshall stared down Jackson. The “criminal alien” these critics conjure bears no resemblance to the misdemeanor defendant standing before her, just as their cartoon empress-judge bears no resemblance to the flesh-and-blood Dugan, who likely never imagined her routine courtroom management would end with the cold snap of federal handcuffs.

Her crime wasn’t arrogance but adherence to the ancient compact between judge and court—that this space, these proceedings, have integrity that any authority, however powerful, cannot casually breach.

A common justification for aggressive immigration enforcement tactics is public safety concerns. While public safety can be a legitimate priority in some cases, the circumstances surrounding Eduardo Flores Ruiz’s arrest reveal different motivations. If Flores-Ruiz honestly presented an urgent threat to public safety, federal agents would not have allowed him to freely walk through the courthouse, ride in elevators, and move through public spaces. The agents maintained visual contact with him throughout this time, hardly the protocol for someone considered dangerous enough to warrant immediate detention.

The state court had already assessed any potential risk by granting Flores-Ruiz bail for his misdemeanor domestic-related charge, indicating local authorities didn’t consider him a significant threat to community safety. Federal agents could have easily waited until after his court proceedings concluded to make their arrest. This standard practice respects the judicial process. Instead, the timing and manner of enforcement suggest the spectacle itself was the goal. For those genuinely concerned about community safety, courthouse arrests like this have a chilling effect that discourages immigrants from participating in the justice system as witnesses, victims, or defendants, ultimately undermining the very public safety such tactics claim to protect.

Jessica Vaughan’s claim that these cases represent “shocking expressions of obstruction of legitimate immigration enforcement” exemplifies this emotional framing. Her assertion that judges are “supposed to uphold the law, not help people evade it” simplistically ignores the complex balance of dual sovereignty that has defined our constitutional system.

Vaughan, Director of Policy Studies at the Center for Immigration Studies, frames the issue as judges creating “escape hatches” that establish “a double standard that can destroy the public faith in an impartial judiciary system.” Yet this perspective ignores the critical distinction courts have established between “refusing to help” and “impeding” – a legal principle central to these cases. Her analysis also overlooks the legal requirements for obstruction and concealment charges, including the “hiding” element that cannot be satisfied when federal agents maintain visual contact with the subject.

The American Bar Association’s Immigration Commission has criticized this analytical approach for ‘substituting selective anecdotes for comprehensive legal reasoning.’ Similarly, former federal prosecutors from Republican and Democratic administrations have noted that such commentary often lacks the precise legal analysis required when evaluating the elements of criminal statutes.

The Path Forward: Law Over Spectacle

The delicate balance of federalism requires vigorous federal enforcement and respect for state judicial autonomy. This isn’t a zero-sum game – the “republic will still stand if ICE respects the state bench and state procedures,” as Judge Gertner wisely notes.

Our constitutional system was deliberately designed to prevent one level of government from dominating the other. By following established legal principles rather than creating media spectacles, we can navigate these tensions in ways that preserve order and liberty. The anti-commandeering doctrine, proper application of concealment statutes, and respect for judicial independence provide roadmaps for resolving these conflicts without the polarization that threatens to fracture our republic.

The law, not emotional reactions to courthouse arrests captured on camera, offers our best path through these complex constitutional questions that have challenged America since its founding. This is where America’s soul gets forged, in the white-hot crucible of power clashing with conscience, without guaranteeing which side will prevail.

This tension isn’t a bug in our system – it’s a feature that preserves local democracy and prevents federal overreach while still allowing for national policies. Rather than seeing this as obstructionism, we might view it as the constitutional checks and balances working exactly as designed.