Video Shows Judge Dugan Helping Criminal Migrant Escape Courthouse

We’ve all heard the story at this point but yesterday a local news channel got video of the incident in response to an open records request they had filed a month ago.

The video, released by Milwaukee County through an open records request, is part of the evidence in the case against Judge Dugan, who is charged with obstructing a federal investigation by concealing Flores-Ruiz and allowing him to leave her courtroom through a different door after directing the agents to speak to the chief judge.

The footage shows Judge Dugan, wearing her black robes, confronting federal agents at the Milwaukee County Courthouse. Prosecutors allege Dugan obstructed the federal investigation by allowing Flores-Ruiz to leave her courtroom through a restricted exit typically used by jurors.

According to prosecutors, federal agents were redirected to speak with the Chief Judge, while Flores-Ruiz exited the building.

After Flores-Ruiz and his attorney snuck out a non-public door (allegedly) with Judge Dugan’s help, they quickly got on an elevator. Fortunately, one member of the arrest team spotted them and got on with them. He followed the down and out of the building. You can see him talking on his phone as he trails them out the exit. Once outside, Flores-Ruiz ran for it and was stopped about a block away and arrested.

Judge Dugan was arrested one week later, according to a criminal complaint, and indicted on May 13 after a federal grand jury found probable cause to move the case forward.

Her attorneys filed a motion to dismiss, citing judicial immunity for her official acts.

On May 15, she pleaded not guilty to the charges and is due to appear in federal court on July 9 for a pretrial hearing.

As I noted here, there are various takes on whether or not Judge Dugan’s case will actually get to trial. Some observers think the case against her is pretty solid, but Elie Honig argued the facts may not matter.

While the complaint against Judge Dugan makes out a valid criminal charge, the odds of an ultimate conviction are minuscule. It will come as little surprise if a federal district-court judge dismisses the case, or even if a grand jury declines to indict; the politics around this case run hot, and it feels precipitous to prosecute a judge for her conduct inside her own courtroom. Attorney General Pam Bondi made matters worse when she amateurishly gloated on Fox News about prosecuting “deranged” judges; that improper public commentary also could provide a hook for dismissal if a federal judge is determined to find some off-ramp.

If the case makes it to trial, it’ll be exceedingly difficult to convince a jury of 12 Wisconsin residents to convict Judge Dugan given the politics around the case. Wisconsin is split roughly in half; Trump won the state in 2024 by less than one percentage point. Jurors who oppose Trump or his anti-immigration policies will have a hard time putting aside their political views, no matter the actual evidence.

In short, jury nullification because Trump is a really possibility in this case.

Flores-Ruiz remains in federal lockup after being charged with reentering the US after being deported in 2013. He has pleaded not guilty in that case and his next court date on the federal charges is in a month. Meanwhile, the domestic violence case that brought him to court that day is still pending. He has a court date for that case in just under a month.

As for Judge Dugan, assuming no plea agreement is reached, she’s facing a jury trial set to start on July 21. Here’s the video.