Judge's Alleged Intervention Leads to Deportation and Federal Charges
A controversial case involving a Milwaukee judge and an immigrant she allegedly helped evade federal authorities has reached a critical juncture with the man's deportation. Eduardo Flores-Ruiz, 31, has been removed from the United States by the Department of Homeland Security after pleading guilty to illegally reentering the country.
The development marks a significant turn in a saga that has seen Milwaukee County Judge Hannah Dugan indicted on federal charges and could result in her facing up to six years in prison if convicted.
The Sequence of Events: From Mexico to Milwaukee and Back
According to official court documents, Flores-Ruiz first left his home near Michoacan, Mexico, in 2013 at age 18, entering the United States illegally. He was apprehended and deported immediately after crossing the border but managed to reenter the country just days later.
For approximately 12 years, he lived and worked in Milwaukee's restaurant industry until March 2025, when he was charged with three counts of misdemeanor battery following an alleged altercation with his roommate. It was during this criminal proceeding that his immigration status came to light after the Milwaukee County Jail submitted his fingerprints to federal databases.
The situation escalated on April 18, 2025, when Flores-Ruiz was scheduled to appear for a hearing before Judge Dugan. Immigration and Customs Enforcement (ICE) agents had planned to arrest him at the courthouse, but prosecutors allege that Dugan learned of their presence and orchestrated his escape.
Court documents state that Judge Dugan led Flores-Ruiz out of her courtroom through a private door, allowing him to exit the building. Agents subsequently captured him after a foot chase through the streets.
Legal Fallout and Judicial Defence
The aftermath has been substantial for both individuals involved. A federal grand jury indicted Judge Dugan in May 2025 on charges of obstruction and concealing an individual to prevent arrest. Her trial is scheduled to begin on December 15, 2025.
In a statement that underscored the gravity of the situation, the Department of Homeland Security commented: "Judge Hannah Dugan's actions to obstruct this violent criminal's arrest take 'activist judge' to a whole new meaning. Thanks to the brave men and women of ICE law enforcement, this criminal is OUT of our country."
Judge Dugan has maintained her innocence, asserting her right to manage her courtroom as she sees appropriate. Her legal team has referenced an email from Milwaukee County Chief Judge Carl Ashley, sent approximately two weeks before Flores-Ruiz's arrest, which stated that courts must remain "safe havens" from immigration enforcement.
Meanwhile, Flores-Ruiz spent most of the past seven months in custody. State prosecutors dropped two of the three battery charges against him in October 2025 after he agreed to plead no contest to the third count, receiving a sentence of time served.
On November 6, 2025, U.S. District Judge Pamela Pepper similarly sentenced him to time served for the illegal entry charge, following his guilty plea and agreement not to contest deportation. The Department of Homeland Security confirmed his deportation on Friday, November 14, 2025, though did not specify whether he was returned to Mexico or another destination.
