ICE protesters keep beating Trump in Chicago court, but the battles take a toll. 'It’s about intimidation'

Photographs of Ray Collins and Jocelyne Robledo in federal custody are just a Google search away, as easy to find as the social media posts calling them “armed rioters” and “deranged individuals."

Authorities arrested the Englewood couple five months ago outside of an immigration processing center in Broadview, just weeks after President Donald Trump launched a pummeling deportation campaign across the Chicago area last September.

Their assault cases quickly fell apart when a grand jury refused to indict. Collins still found himself being called “everything from a thug to a predator.” And he now has a warning for potential employers who might try to look him up: “I was arrested for a felony.”

“It’s almost embarrassing,” he told the Chicago Sun-Times.

But he’s resilient.

“I know myself and my character, that those things would never stick,” Collins said. “They can’t tarnish what I’ve done in my community. They can’t tarnish who I am as a person.”

Collins and Robledo are among a growing number of protesters who have been left to pick up the pieces after taking on the Trump administration in court — and winning.

Prosecutions for nonimmigration crimes tied to Operation Midway Blitz have disintegrated at an alarming rate at the Dirksen Federal Courthouse since October. Cases against 17 of 32 known defendants have already collapsed, including the ones against Collins and Robledo.

But they still come at a cost. A federal prosecution is intimidating. It carries the threat of prison time. Damaging news stories spread online. Freedoms are often restricted, even in minor cases. Lawyers are needed, though federal defenders have saved people from big legal bills.

Then there’s jail.

The 17 cleared defendants spent a combined 150 days in federal custody, records show. That doesn’t include 35 days, and counting, that Juan Espinoza Martinez has been held by immigration authorities since he was acquitted for allegedly placing a hit on Gregory Bovino, the Border Patrol official who became the face of the deportation operation.

That’s to say nothing of the flesh-and-blood cost borne by Marimar Martinez, the woman shot five times by a Border Patrol agent on the Southwest Side in early October.

The stakes aren’t so high in every case. Jackie Guataquira, whose four-month old misdemeanor case was recently dropped, said she never spent a night in jail and didn’t have to physically appear in court. But the prosecution kept her from visiting family in Mexico, Guataquira said.

It just shows “they want to come for people at every single level,” she told the Sun-Times.

“They’re really just trying to take people’s lives away, deport them out of this country, or at the … more minor level, paint people who are righteously protesting and standing up to this as ‘terrorists,’” she said. “They’re slapping these people’s photos all over social media for this, just to get people away from being able to protest.”

‘Your life gets turned upside down’

Federal prosecutors are expected to bring charges only when they can prove them to a jury beyond a reasonable doubt. Normally, they boast a conviction rate of around 90%. But Trump’s Justice Department has suffered a string of high-profile losses tied to its national immigration campaign, including in a recent six-case losing streak in Los Angeles.

In Chicago, U.S. Attorney Andrew Boutros’ office is looking at a best-case conviction rate of around 47% in such cases. That’s assuming it secures a conviction against each of the remaining 15 defendants, and no additional charges are brought.

Boutros said many of the cases were brought as a result of “reactive arrests” in the field. Some of them were better suited for state court, he said. Others were dropped out of concern that jurors would reject charges even when they’re proven, or for mitigating factors like mental health.

“Our grace should not be confused as a reflection of the strength of any particular case or whether a charge should have been filed,” Boutros said in a statement. “It is a testament to our view that the role of the prosecutor is to seek justice and not just convict.

“We decide cases based on facts, law, and equities without regard to the attitude of sneering disbelief held by a certain group of critics.”

Attorney General Pam Bondi initially appointed Boutros to his job on a temporary basis in early 2025. Chicago’s U.S. District Court judges then picked him to serve on a more permanent basis once Bondi’s appointment expired.

Laurie Levenson, a professor at Loyola Law School in Los Angeles, said there are “enormous consequences” when someone is charged with a federal crime. That’s true even if the prosecution is abandoned, Levenson said.

“Your life gets turned upside down when you’re charged with a federal case,” Levenson said.

But the greater cost, she said, is to “the credibility of the justice system.”

Charges dropped — but damage is done

Authorities arrested Collins, 32, and Robledo, 30, on Sept. 27 outside the U.S. Immigration and Customs Enforcement facility in Broadview, which became a hub for fierce protests.

Three days earlier, a shooter opened fire on an ICE facility in Dallas. Emotions ran high. Without naming the couple, Bovino referred to Collins and Robledo online as “two deranged individuals, armed with pistols.” Users on X shared his social media post 278 times.

“Don’t find out the hard way,” Bovino wrote.

Collins and Robledo never faced any charges related to the guns, which they were lawfully carrying and never brandished.

Instead, a criminal complaint alleged that Robledo ignored commands and pushed back when law enforcement told people to move.

Once officers began to struggle with Robledo, Collins allegedly yelled at them to get away and charged toward them. The feds said Collins resisted agents — and injured one agent’s thumb. Collins told the Sun-Times he "did not start" the altercation and "did not assault anyone."

Prosecutors later sought to have the couple detained. U.S. Magistrate Judge Gabriel Fuentes ruled that Robledo didn’t qualify for detention. Collins did, because of the agent’s injury, and Collins’ attorney insisted on an immediate hearing.

The judge ordered Collins detained. He questioned Collins’ judgment in bringing a gun to an ICE protest, “particularly given ICE’s recent history of aggressive enforcement tactics while heavily armed.”

Robledo said Collins, who is Black, was seemingly held in jail longer “simply because of the color of his skin.” Collins said he suspects the judge “subconsciously” assumed “I carried and I was a dangerous individual because of my presentation in court, my looks, and the area that I’m from.”

In his written order, Fuentes said the defense request for an immediate hearing left him without a report that might have addressed Collins’ employment and lack of criminal history, as well as his personal background. The decision “was an extremely close call,” the judge wrote.

Fuentes predicted that a reviewing judge could take advantage of “a more fulsome record.”

Three days later, U.S. District Judge Sunil Harjani ordered Collins’ release with that additional information in hand.

Then, on Oct. 8, the feds dropped the charges. A grand jury had refused to indict, in a rare rebuke of federal prosecutors.

The time spent in jail was “nerve-wracking,” Collins said.

“Not because I was scared that I was in federal prison,” he explained. “But just the stress of knowing that I can’t take care of my pets, my family. That the justice system does not work even when you haven’t done anything wrong.”

Robledo has been hesitant to join protests in Broadview ever since. As someone who has been involved in demonstrations since the age of 13, Robledo said that’s “life changing” — but insisted it’s not “life ruining.”

“It makes it harder for you to do anything,” Robledo said of the prosecution. “That’s the point, right?

“But I decided a long time ago that that wasn’t going to happen to me.”

Fuentes has since questioned some of the charges brought amid Operation Midway Blitz, including against Collins and Robledo. He did so in an opinion issued in late November, after a series of cases before him fell apart.

The judge wrote that he’d “obtained sworn confirmation that video backed up” the feds’ claims against Collins and Robledo. Still, he wrote, “the grand jury refused to find probable cause.”

“That is a sobering event for a magistrate judge,” Fuentes wrote.

He added: “Any responsible federal prosecutor knows that federal charges, or any actions by the United States attorney directed at the citizenry, must be undertaken with the utmost care.”

‘Levels of repression’

Martinez has become the most prominent of the 17 cleared Midway Blitz defendants in Chicago. She testified recently before Democratic members of Congress. She also attended Trump’s State of the Union address Tuesday as a guest of U.S. Rep. Jesus “Chuy” Garcia, an Illinois Democrat.

But in early October, she found herself recovering from her bullet wounds for one night in the Metropolitan Correctional Center. The 30-year-old Montessori school teacher’s assistant said it was “everything you see in the movies.”

She said she learned not to trust anyone there, including the guards.

“I remember, I used to hear the inmates above banging, making beats on the walls,” Martinez said in a recent interview. “It was surreal.”

Martinez spent 46 days charged with assaulting the Border Patrol agent who shot her, Charles Exum. Then, on Nov. 20, federal prosecutors abruptly dropped the charges against her and another man, Anthony Ian Santos Ruiz.

Homeland Security officials labeled Martinez a “domestic terrorist” and have refused to rescind the claim, even though a social media post about Collins and Robledo seems to have disappeared.

ICE officials did not respond to a request for comment about Collins and Robledo.

Only one Midway Blitz case has gone to trial, so far. The feds accused Espinoza Martinez, 37, of offering $10,000 for Bovino’s murder. Espinoza Martinez spent 109 days in jail — far more than any other Midway Blitz defendant who's been cleared.

His prosecution revolved around a Snapchat message he sent to an acquaintance that purportedly offered $2,000 for Bovino’s capture and $10,000 for his head. Espinoza Martinez is a Mexican citizen and father who lived in Chicago for 30 years and has no criminal history, records show.

He told agents he didn’t mean for anyone to actually carry out the murder.

The jury found Espinoza Martinez not guilty on Jan. 22. But Homeland Security took him into custody the next day, as he was being released from the MCC. He’s still being held in the Clay County Justice Center in Indiana, after an immigration judge found that he posed a “potential” danger to the community.

Espinoza Martinez only landed on the feds’ radar because of the Snapchat message he sent, prosecutors said during the trial.

The consequences for every Midway Blitz defendant haven’t been so severe. But Guataquira, 30, says it shows how people are being targeted by the feds “even at the most ‘minor’ level.”

For 19 weeks, Guataquira faced a misdemeanor charge alleging she’d impeded a federal employee in Broadview. She told the Sun-Times she was accused of knocking a phone out of an agent’s hand Oct. 3, the day Homeland Security Secretary Kristi Noem visited the ICE facility.

Prosecutors finally dropped the case against Guataquira on Feb. 18.

Guataquira said she was held in custody for about six hours but never overnight. She said she’s since spent her days traveling and never had to attend court in person. She reported to the U.S. Marshals office over the holidays to be processed.

But authorities took her passport. She said that prevented her from visiting family in Mexico and otherwise crossing the border during her travels.

“We wanted to go to Vancouver Island when we were in Washington,” Guataquira said. “Could not do any of that. So that was, I think, one of the biggest things that bugged me.”

It all amounts to “different levels of repression,” she said, “from the legal end of things to your livelihood.”

Sullied reputations

Levenson, the Loyola law professor, is also a former federal prosecutor. She said Trump’s second term brought significant change to the Justice Department, where top officials seem to be “using the power of prosecution for revenge and retribution.”

“I think it’s about chilling demonstrators," Levenson said. “It’s about intimidation. It’s about flexing the federal muscle.”

Even a misdemeanor case like Guataquira’s carries a threat of prison time.

“All you know is that the government’s being extremely aggressive,” Levenson said. “So you think of the worst.”

There’s limited legal recourse available to people caught up in failed federal prosecutions, she said. Meanwhile, the ensuing news coverage damages people’s reputations.

“What people first see is that you’ve been arrested,” Levenson said. “They often don’t follow the resolution of the case. And so, the name calling that has occurred can have irreparable damage on individuals, even if the case is dismissed. They have a label that is put on them and it’s very hard to get that removed from the public psyche.”

Levenson said it could “take years to repair any trust in credibility in the Justice Department,” including within the judiciary, following so many failed prosecutions.

“What really troubles me,” Levenson said, “is there is real crime out there.

“But if you’re busy spending your time, money, [and] energy on cases where, ultimately, they will be or should be dropped,” she said, “then you’re not protecting society.”