Freddy Cazares arrived at his lawyer’s office in Pilsen a few minutes early on a gray Thursday morning in August, ready to sign the documents that he hoped might provide some measure of security and peace. In the 11 months since his detainment during Operation Midway Blitz, he’d learned to live without much of either.

His release early last December, he said, had been “like a miracle.” It came after 80 days locked away, first in the Immigration and Customs Enforcement processing center in Broadview — where “they treated us worse than animals,” he said — and then in a jail about 200 miles south, in rural Clay County, Indiana.

For most of his detainment, he waited to be flown out of the country. He’d signed deportation papers under duress, he said, and when agents drove him and other detainees from Broadview to an airport he waited for his name to be called. But then the plane filled and he never heard his name, and “they put us back in a van and took us to Indiana.”

Almost three months later, a judge ordered his release. Cazares, 38, had been praying for it. He has a wife. Three American-born children. No criminal record. He’d crossed the border from Mexico as a teenager and eventually settled in Wheeling. The United States has been his home for more than 20 years. Whatever elation he felt upon his release, though, proved fleeting.

Cazares entered into a prolonged limbo that could end in deportation anyway. In the Chicago area, he was among nearly 3,800 immigrants who were arrested and detained during Operation Midway Blitz, according to a Tribune analysis of ICE data provided by the research group Deportation Data Project. Among those, more than 1,000 ultimately won their release.

They soon learned that didn’t necessarily mean freedom.

For immigrants without legal status, release is often framed as a victory. In reality, it is usually temporary, conditional and far from secure. Years can pass before an initial court date. A final resolution can take much longer.

Operation Midway Blitz, one year later

Some, like Cazares, are granted parole. They may even receive work permits. The reprieve allows them to rebuild their lives — however temporary — while their cases slowly drag through a backlogged court system. But immigration attorneys say release may simply mean continuing court proceedings outside detention before deportation.

“The release in and of itself is about human dignity and due process,” said Jennifer Babaie, the associate director of the Adult Detention Project at the National Immigrant Justice Center. “But it is just one step on a still Herculean effort to try to go through all of the legal loopholes you need to try to retain any kind of legal status here.”

For many, a release isn’t necessarily a new start. It is instead part of a long goodbye.

**

Cazares begins most days at sunrise and works construction or as a day laborer throughout the city and suburbs. He would have rather been working the morning of his appointment the first week of August but instead arrived a few minutes before 10:30 and walked through the doors of the Pilsen branch of The Resurrection Project, a Chicago nonprofit dedicated to immigrant advocacy.

He brought his 14-year-old nephew to help translate, if needed, and one of his sons. Cazares looked nervous as he took a seat and waited. Much of the past year has been one long test of his perseverance, and there is no way to know when it all might end. Or where.

A door swung open and Elizabeth Suarez, a paralegal, called his name. He followed her up a narrow stairway and into a small office with block glass windows that allowed light but no view, and he took his seat on the other side of her desk. A stack of papers awaited and Suarez walked him through the forms and the boxes that required his signature.

“Make sure everything is in order,” she said, speaking to Cazares in Spanish. “Please double-check your name every time. It’s with a Z, right? I always forget. Phone number. Your current address.”

“Si,” Cazares said quietly, thumbing through the documents.

“So, if everything looks good, please sign here,” Suarez said.

He signed the forms and Suarez made copies and that was it. An appointment of about 10 minutes.

If all went to plan Cazares would receive a work permit in the mail, and it would offer a layer of protection. It was another step to show he was trying to do the right things, along with the scheduled check-ins with ICE and avoiding even the most minor of run-ins with the law.

The largest question, though, hung over him:

Would he be allowed to remain in the country that has been his home for 22 years?

Those who are released, and want to stay, experience similar uncertainty while they navigate contrasting legal journeys. Some will fight asylum cases. Others will continue visa applications. Some will seek legal status through family members who are U.S. citizens or permanent residents.

For Cazares, detainment created a pathway that otherwise would not have been available, said Peter Meinecke, senior staff attorney at The Resurrection Project. Some like Cazares, who’ve been in the U.S. at least 10 years, are eligible for cancellation of removal. If an immigration judge grants Cazares the order, he can obtain lawful permanent residence.

That creates a complicated situation, Meinecke said, because detention can ultimately give someone access to a form of relief for which they could not previously apply. Losing the case, though, could also result in deportation.

“If you don’t win, then you run the risk of getting a removal order,” Meinecke said. “If you win you get a green card.

“It’s really fascinating to me. Like who created this incomprehensible system? It’s insane.”

**

Cazares won his release like many — if not most — who were detained during Operation Midway Blitz: through habeas corpus, a 200-year-old American legal doctrine that has surged as a defense strategy amid President Donald Trump’s immigration enforcement operations.

Habeas corpus, which allows a defendant to challenge the legality of their imprisonment, is among several mechanisms for release, some of which depend on a detainee’s location. In some cases, a release might come through a judge who grants bond. In others, ICE can grant bond, or parole.

Unlike criminal cases, in which a person may be able to post a percentage of the bond, an immigration bond generally must be paid in full before release. The costs vary widely and depend on several factors, said Katherine Greenslade, managing director of The Resurrection Project.

“They look at how long they’ve been here,” she said. “Do they have U.S. citizen or legal permanent resident family? What sort of community ties do they have?”

Those released often receive a check-in appointment within a few weeks, Meinecke said, and must meet conditions — wearing an ankle monitor, for instance, and keeping documentation — while their cases continue. A violation can lead to re-detainment.

In February, a little more than a month after his release in Clay County, Indiana, Cazares was back at an ICE facility. This time at the Office of Enforcement and Removal Operations for a check-in to determine, again, whether he would be allowed to pursue a case or be forced to leave the country.

His hands trembled as he walked into a large room with gray chairs against tall white walls. “Deport voluntarily,” one sign read. The same message was posted in nine languages.

He sat and leaned his head against the wall.

“Ojalá todo salga bien. Que sea lo que Dios diga,” he said, praying: I hope everything goes well. Whatever God wills.

A young ICE agent appeared and asked a boy who’d accompanied Cazares to translate a message.

“Basically, he is out on parole. So no traffic violations or anything like that, and you won’t hear from us,” the agent said as he handed Cazares a document with the information. Cazares smiled with relief. His next check-in is scheduled for January 2028.

He folded the paper and put it in his wallet.

**

He considered his release a miracle because of its improbability. Like something divine. Like many who were detained only to be released, Cazares needed a combination of luck and legal might.

He expected to be deported. He’d signed the papers during a confinement in Broadview that he described as harrowing: detainees sleeping on the floor and next to toilets; officers imploring Cazares and others to sign away their lives in America to go back to their home countries, no matter how long it’d been since those countries were home.

“They said if I didn’t sign, they would punish me,” Cazares said.

Not long after signing, Cazares boarded a bus to the airport, where he waited for a moment that never came. At least not for him. At the jail in Clay County, he contacted his wife for the first time since his arrest. She connected him with Andrés Díaz, an attorney from The Resurrection Project.

Among Díaz’s first questions for Cazares was this: Do you want to accept deportation? Or do you want to fight? Until then, Cazares believed he was destined for deportation, or worse.

“I thought I was going to die in there,” he said.

**

Until recently, immigration attorneys used habeas corpus only on rare occasions. It used to be reserved for people navigating prolonged detainments in extreme, outlier cases.

But then the second Trump administration began and, with it, the immigration enforcement operations that swept over the country and arrived in Chicago with militant force. As the Broadview detention center filled, and while federal agents moved detainees from there to jails in Indiana and Kentucky and elsewhere, habeas corpus emerged as a viable legal tool.

“It’s only really under this new administration where it’s just become this absolutely necessary prerequisite to get pretty much anyone out of detention,” said Carlos Estrada, a senior litigation attorney from the Illinois Habeas Project for the National Immigrant Justice Center.

Operation Midway Blitz came with the promise of targeting the so-called “worst of the worst criminal illegal aliens” in the city. Quickly, it became clear that agents instead targeted anyone who appeared to be Latino.

Cazares was installing siding during a job in Naperville when he was detained. And like him, the vast majority of those arrested during the blitz had no criminal record.

“We’ve seen them pretty much indiscriminately pick up anyone and everyone without a warrant, without probable cause, including people who they themselves had released on parole or on an order of supervision,” Estrada said. “For most of these folks, the government could process their cases without detaining them.”

Successful habeas petitions do not necessarily lead to quick resolutions. For those detained in the blitz and released, the average stay in custody lasted 2 ½ months. Those released often found themselves far from where they were detained. Cazares needed a friend to pick him up in Indiana. Some in Broadview had been sent to facilities in Texas and Arizona.

For Cazares, and many who decided to fight their cases, detainment represented the beginning of the effort to gain legal status. Cazares in June applied for a form of relief known to immigration lawyers as “non-LPR cancellation of removal” — LPR an acronym for lawful permanent resident.

In addition to the 10-year residency requirement, applicants need a clean criminal record, and to have been “a person of good moral character.” The final requirement is perhaps the most difficult to meet: They have to establish that “removal would result in exceptional and extremely unusual hardship” for family members who are U.S. citizens.

The thought of being separated from his children haunted Cazares. It also pushed him to fight.

“I couldn’t even get out of bed anymore,” he said. “The only thing that kept me going was seeing my children again.”

At home after his release last Dec. 8, the relief gave way to long-term anxiety. His children have been “suffering,” he said, and their grades have gone down. He has told them to focus while his case continues. He has told them that all they can do is to move on and keep going.

But Cazares doesn’t know where he’s headed, exactly.

“I got out of that hell, but it still feels like it’s out here,” he said.

The outcome of any given relief case is “very judge dependent,” said Meinecke, of The Resurrection Project, and while he believed in Cazares’ case he acknowledged the uncomfortable truth: There were hardly any guarantees.

A green card, deportation, another detainment — they all remain possible. While Cazares tended to his paperwork during his August visit, Meinecke and a few others worked in a small space upstairs. The “endless cycle,” as he put it, of detainments and delayed releases and far-off court hearings had made for busy times for immigration lawyers.

It also left people in legal purgatory. Cazares’ far-off next court date, not until 2028, is not atypical, Meinecke said, given the backlog of cases in the fallout of the blitz.

“This is all a result of a broken system,” he said. “Like, a decades-long broken system.”

**

The system is a maze in which laws collide with gray areas, where layers upon layers of policy have accumulated over decades in a pile waiting for reform that has never come.

“The fact that it doesn’t make sense is entirely consistent with the history of the U.S. immigration system,” said Nicole Hallett, a clinical professor of law and director of the Immigrants’ Rights Clinic.

It is a system that has created a paradox, and led to a large population of undocumented immigrants who lack a straightforward path to permanent legal status. The laws that limit their entry in the first place “have not discouraged people from coming,” Hallett said.

“But it has meant that the undocumented population has grown over time because it’s very difficult to legalize your status once you’re here.”

The tension is particularly clear in temporary immigration programs. Temporary Protected Status, for example, provides protection from removal, and work authorization to eligible nationals of designated countries under certain circumstances.

But it does not provide a path to lawful permanent residence or citizenship. The Department of Homeland Security has acknowledged that some have remained in TPS for decades.

The problem with temporary status is not simply that it is temporary, Hallett said. It is what happens when people build permanent lives while living under a temporary designation.

The U.S. has repeatedly attempted to overhaul its immigration system, but reform has failed to become law despite major legislative efforts. Hallett, acknowledging the complexity of reform, said the difficulty goes beyond partisan politics.

“It’s not like there’s a clear fix for all of this stuff,” she said, adding that “we’ve stopped even talking about it because it just seems such a remote possibility that it’ll happen.”

**

Cazares’ story is hardly an outlier. It is more the norm. Walter Pascual said he tried for years to obtain legal status after he entered the country in 2005 from Guatemala.

He learned he first needed to be arrested and detained.

“Literally, there’s no way” otherwise, he said.

“All the people who have been here 20 years, 30 years, and who have never had contact with immigration, if they don’t have children, if they don’t have anything, if they haven’t married a citizen, there is no way.”

Pascual has gained a following on social media for documenting immigration enforcement in and around Chicago. He was working as a driver last October, on his way to a pickup at a hotel, when he was arrested. He can remember what one of the federal agents told him:

“Welcome, Walter. We’ve been waiting for you.”

Pascual, 37, spent almost three months in detention. He’ll spend years in uncertainty before he knows if he can remain in the country. For the first time, though, he has a work permit, which offers some level of protection while his case continues. He said he’s not scared — “I have a little bit of concern, but not fear” — but he may well be an anomaly that way.

In another part of Chicago, a 48-year-old man named Jose — who only wanted to be identified by his first name — remains afraid to leave home. He spent 76 days in federal custody. Agents apprehended him early last October, when he’d been working his landscaping job, cutting grass.

He wound up in Broadview. Then in a jail in Missouri. He paid a $10,000 bond to be released, but only after his sister gave him half and his three children and neighbors raised the rest. And he now must raise more money to pay the attorney working his case. He is at home now but not free.

He has no criminal record. Three American-born children.

“If I have to leave, what are they going to do?” he asked of his family.

There’s nothing for him to do but wait and hope. In the aftermath of detainment, the released carry burdens that manifest in a variety of trauma responses, said Lu Rocha, a Chicago therapist.

“Anxiety, panic attacks, hypervigilance, very easily startled, flashbacks, insomnia, inability to fall asleep for fear of dreaming about the traumatic events,” she said.

Jose hesitates to go to McDonald’s. What if ICE approaches him while he’s there?

Inside the Missouri jail, he was surrounded by those also facing deportation. He said about 50 people from the Chicago area were transported there at the same time he was. Eventually, only about 10 remained. Some were deported. Others were released on bonds that varied widely.

One person paid $5,000. Another paid $7,500. Someone else paid $20,000. Jose’s was $10,000.

He’s still trying to pay back those who raised the money. He’s still waiting for his work authorization, and his next court date. And he is still trying to understand what release ultimately means. Jose keeps the same paperwork that an ICE agent handed Freddy Cazares. They treat the documents like amulets, as if they have the power to keep them safe.

Immediately after their release, they experienced the obvious range of emotions. But now there’s the lingering unknown amid a fight that can feel endless.

“I came here to work and pay taxes,” Cazares said. “I’m not a bad person.”

His August appointment at The Resurrection Project represented one more step in a long journey. He walked downstairs when it ended and the clouds of a rainy morning were starting to break. There was plenty of daylight left and Cazares decided to do what he’d done most days since arriving in America 22 years ago: He set out to go work.