by Paul Kiefer / Wisconsin Watch, Wisconsin Watch
July 28, 2026
The chief federal judge for Wisconsin’s Eastern District has begun clearing a path to bond hearings for immigrants in U.S. Immigration and Customs Enforcement custody, months after attorneys first asked her to rule on challenges to the Trump administration’s mandatory detention policy.
Over the past month, Judge Pamela Pepper has sided with at least four immigrants challenging the legality of their detention — her first rulings on a Department of Homeland Security policy that has landed thousands of immigrants nationwide in custody, sometimes for months.
Pepper’s rulings place her among a growing number of federal judges who have rejected the administration’s interpretation of immigration law. But courts nationwide remain divided over whether immigrants can seek release from ICE custody while fighting their deportation cases.
Those disagreements have created a patchwork of rulings that federal appeals courts or the U.S. Supreme Court may ultimately resolve.
Pepper, appointed by then-President Barack Obama in 2014 and the district’s chief judge since 2019, is among the last of her colleagues to rule on the issue.
New detention policy sparks dispute
The dispute centers on opposing interpretations of a decades-old federal law.
The 1996 Immigration Reform Act requires immigration authorities to detain — without bond — anyone found crossing the U.S. border without authorization. Prior administrations applied that rule narrowly, allowing many immigrants arrested in the country’s interior to seek a bond hearing in immigration court.
The Trump administration bucked that approach in July 2025, when ICE Director Todd Lyons issued a new legal interpretation requiring detention without bond regardless of where immigrants are arrested.
The Board of Immigration Appeals, a panel of judges who set the rules for the federal immigration court system, signed off on the interpretation in September.
With bond off the table, thousands of immigrants in ICE custody have turned to a backup option: filing habeas corpus petitions in federal district courts to challenge their detention. Unlike immigration courts, which are part of the U.S. Department of Justice, federal district courts belong to the judicial branch and, therefore, are technically independent of the White House. When a federal district court grants a habeas petition, it generally orders an immigration court judge to hold a bond hearing.
If the district court judge grants the petition in time for an immigrant to leave custody on bond, the person’s removal case moves to the slower-moving “non-detained” docket, buying time to build a case for staying in the U.S.
The mandatory detention policy has triggered tens of thousands of habeas petitions over the past year, overwhelming the federal prosecutors responsible for defending ICE detentions. Wisconsin accounts for roughly 100 of those cases, filed in its Western and Eastern District courts. Pepper received 15, more than any other Eastern District judge.
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Judges split over Trump policy
Legal battles over the validity of the mandatory detention policy are still unfolding in federal courts nationwide.
Judges in Wisconsin’s Western District have uniformly rejected the mandatory detention policy while those in Wisconsin’s Eastern District remain divided.
Eastern District judges Brett Ludwig, William Griesbach and J.P. Stadtmueller — appointed by Presidents Trump, George W. Bush and Ronald Reagan respectively — have consistently upheld the mandatory detention policy.
“It would make little sense to reward those undocumented immigrants who successfully evaded detection upon arrival in the United States and traveled into the interior of the country with discretionary release, while mandating the detention of those individuals who were not so successful or who sought entry at a border or port of entry,” Griesbach wrote in a December 2025 order denying a Venezuelan detainee’s petition.
Judges Lynn Adelman, Byron Conway, William Duffin and Nancy Joseph have each ruled against the mandatory detention policy at least once in the past year. Adelman and Conway were appointed by Democratic presidents; Duffin and Joseph were selected by a panel of judges.
“There are plausible reasons for treating noncitizens who are well-settled in communities, perhaps working jobs and supporting families, differently from new arrivals. As a noncitizen spends years in the country, it is expected that he or she will develop connections to the United States and its citizens that may help establish a defense to removal or a path to permanent legal status,” Adelman wrote in March.
Conway became the first Eastern District judge to rule on the issue last October, when he granted a habeas petition filed by a Nicaraguan man whom ICE agents arrested in Sun Prairie while searching for his roommate. Most Eastern District judges ruled on the mandatory detention policy within one to two months of receiving a petition challenging the policy.
Pepper didn’t grant a habeas petition until June, more than six months after that Nicaraguan petitioner sought the court’s intervention. She has yet to deny a petition.
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Pepper echoed Adelman’s reasoning in her recent rulings, arguing in a June 17 order that the Trump administration’s interpretation of the 1996 law “cannot be squared with the text of the statute.”
Her order also noted inconsistencies within the federal appeals court that could settle the question in Wisconsin. Judges on the Chicago-based 7th Circuit Court of Appeals, which hears appeals from Illinois, Indiana and Wisconsin, remain divided on the detention policy.
The U.S. Department of Justice requested in May that the 7th Circuit hold expedited oral arguments, but it has yet to do so.
Appellate courts based in New York, Cincinnati and Atlanta have ruled against the Trump administration’s policy. Courts based in St. Louis and New Orleans have sided with the administration. The Louisiana-based court has jurisdiction over most of ICE’s largest detention facilities.
The question may eventually fall to the U.S. Supreme Court.
“It’s up to the justices whether they want to take the case,” said Milwaukee immigration attorney Marc Christopher, “but traditionally on cases involving immigration, cases where there’s been a clear circuit split, and where it affects literally tens of thousands of people, I think it’s going to be near the top of the issues they want to resolve.”
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Legal uncertainty, human costs
The lack of clarity only increased pressure for Wisconsin’s federal court judges to begin tackling the growing pile of habeas petitions, Milwaukee-area immigration attorney Jennifer Bizzotto said.
Even if Pepper were not the court’s chief judge, Bizzotto added, “there are so few judges that it really does matter a great deal.”
Pepper’s recent burst of activity brings relief to attorneys and immigrants with cases on her docket, but some lament the long wait’s human toll. “Of course people are happy to be released,” said Claire McNulty, another Milwaukee-area immigration attorney, “(but) how much of a win is it when it’s taken this long?”
“You’re just sitting in detention for months and months with no movement,” Bizzotto said. “These are real people’s lives that hang in the balance.”
Pepper’s recent rulings came too late for at least one immigrant in custody.
Jarwin Martinez Rayo, a Nicaraguan national arrested by ICE officers in Janesville shortly after President Trump’s second inauguration, filed a habeas petition in August 2025. Pepper took up the petition in late January, ordering DHS to respond within a month.
DHS placed Martinez Rayo on a flight to Mexico in mid-February — an increasingly common practice known as a “third-country removal” wherein federal authorities deport immigrants to countries other than their own. The agency did not notify the Eastern District court until June, at which point Pepper dismissed the case without commenting on the administration’s mandatory detention rule.
Bizzotto said the 7th Circuit’s split leaves even more immigrants in limbo.
“We’re all living on borrowed time here,” she said, “and if you want to go for optimism, at least we have one more judge who we know is willing to rule against (the policy).”
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