Freddy Cazares: Navigating the Limbo of Immigration Detainment and Uncertain Release

Freddy Cazares arrived at his lawyer’s office in Pilsen, Chicago, a few minutes early on a gray Thursday morning in August, determined to sign documents that he hoped would offer security and peace. In the 11 months following his detainment during Operation Midway Blitz, security and peace were scarce. His release last December seemed miraculous. After 80 days, initially in the Immigration and Customs Enforcement processing center in Broadview—where he felt treated less than human—and later in rural Clay County, Indiana, locked away, he was waiting to be deported.

During his detainment, he signed deportation papers under pressure and awaited his name at the airport, but it was never called. Instead, he was driven back to Indiana. Three months later, a judge ordered his release. Cazares, a 38-year-old with a wife, three American-born children, and no criminal record, considered the United States his home for over 20 years. Although thrilled by his release, uncertainty loomed over his potential deportation.

Nearly 3,800 immigrants were arrested and detained during Operation Midway Blitz’s raid in the Chicago area, with more than 1,000 released, according to ICE data analyzed by the Deportation Data Project. Although release is often perceived as a win for immigrants without legal status, it usually represents a temporary and conditional reprieve. Initial court dates can take years, and final resolutions even longer.

Operation Midway Blitz One Year Later

Some detainees, like Cazares, are granted parole and may receive work permits while their cases slowly progress through the court system. Immigration attorneys warn that release might merely mean continuing court proceedings outside detention before possible deportation. The release in and of itself is about human dignity and due process, said Jennifer Babaie, associate director of the Adult Detention Project at the National Immigrant Justice Center. But it is just one step in a Herculean effort to try to go through all the legal loopholes needed to retain any legal status here.

Cazares strives to maintain a normal life. On construction or day labor jobs, he works across the city and suburb areas. He arrived early for his appointment in August at The Resurrection Project, a Chicago nonprofit championing immigrant advocacy, together with his 14-year-old nephew to interpret if necessary, and one of his sons.

Cazares looked anxious as he sat down and waited—a year-long perseverance test amid endless uncertainty. Paralegal Elizabeth Suarez soon called him in. In the office, she guided him through signing papers vital for his progress in acquiring a work permit. Make sure everything is in order, Suarez said in Spanish. Please double-check your name every time. It’s with a Z, isn’t it? I always forget. Phone number. Your current address.

After reviewing and signing the documents, Suarez made copies, and the appointment ended in about 10 minutes. If successful, Cazares would soon receive a work permit by mail, offering legal shelter and showing his compliance. It is another attempt to follow all regulations, despite the looming uncertainty over his right to remain in the U.S.

The situation is echoed among many released immigrants—facing uncertain futures amid legal processes. Some pursue asylum claims. Others continue visa applications or seek legal status via family members who hold U.S. citizenship or residence. Cazares’ detention created a potential legal avenue unavailable before, explained Peter Meinecke, senior staff attorney at The Resurrection Project. Individuals like Cazares, who have lived in the U.S. over 10 years, might be eligible for removal cancellation, possibly granting permanent residency. However, losing can mean deportation. If you don’t win, you risk a removal order, Meinecke observed. If you win, you receive a green card. It’s really fascinating to me. Like who created this incomprehensible system? It’s insane.

Using Habeas Corpus

Cazares achieved his release in a manner similar to many detainees from Operation Midway Blitz: by invoking habeas corpus—a 200-year-old legal principle that has surged in use as immigration enforcement has ramped up under President Donald Trump. Habeas corpus enables challenging imprisonment legality and serves as one of several potential release mechanisms, determined by detainee location. Judges may grant bond, ICE may grant bond or parole, but unlike criminal bonds involving partial payment, immigration bonds necessitate full payment prior to release. Costs vary based on factors such as residency length and U.S. citizen or permanent resident family ties, according to Katherine Greenslade, managing director at The Resurrection Project.

Cazares returned in February for another check-in at an ICE facility, which once more determined whether he could pursue his case or face expulsion. Deport voluntarily, a sign read, posted in multiple languages. As his hands trembled, Cazares prayed, Ojalá todo salga bien. Que sea lo que Dios diga. An ICE agent conveyed the message through a translator: Basically, he is out on parole. No traffic violations or anything like that, and you won’t hear from us. Cazares felt relieved; his next check-in was scheduled for January 2028.

The Legal Maze of Immigration

Cazares credited divine guidance for his release. He relied on luck and legal prowess after unexpectedly signing deportation papers under duress amid grim treatment in Broadview’s detention facilities. Once connected to attorney Andrés Díaz at The Resurrection Project, Cazares decided to fight deportation, covering all options. I thought I was going to die in there, he said. They said if I didn’t sign, they would punish me.

Habeas corpus’ usage shifted drastically post-Trump administration initiation. Carlos Estrada, senior litigation attorney for the Illinois Habeas Project at the National Immigrant Justice Center, highlighted newfound necessity under aggressive immigration operations. Operation Midway Blitz aimed to target criminals, but instead detained perceived Latino individuals involved in non-criminal activities. Cazares, among many without criminal records, was detained during a Naperville siding installation job. Estrada assessed ICE’s mitigation claims, revealing indiscriminate arrests, often lacking probable cause.

The Path Forward: Seeking Legal Relief

Successful habeas petitions don’t guarantee swift resolutions. Released detainees averaged about 2 ½ months in custody during the blitz, yet often ended far from detention origin. Detention initiated long efforts for legal status among combatting case releases. In June, Cazares applied for “non-LPR cancellation of removal”—a relief option with requirements including residency over 10 years, clean criminal records, and good moral character. Establishing removal as exceptionally harmful to U.S. citizen family members included the uncertainty of separation. Cazares continued to fight amid worry for his children, affecting their academic performance. Post-release anxiety lingered, impacting his family.

Cazares’ scenario typifies systemic failures influencing immigration legislation. As Nicole Hallett, director of the Immigrants’ Rights Clinic observed, the system and policy-driven legal maze inherently produces contradictions hindering straightforward paths and creating a growing undocumented population without permanent legal status pathways. Temporary immigration programs like Temporary Protected Status further muddle permanent life-building under transient designations, promoting legislative reform struggles.

Despite attempts to reform, legal complexity and politics stall legislation, Hallett pointed out. There’s no clear fix for these issues, she admitted, with reform discussions dwindling and remote prospects for progress. Meanwhile, numerous immigrants endure similar hardship, forced into detainment before seeking legal status.

Walter Pascual faced similar challenges after entering the U.S. in 2005 from Guatemala. Surprised by detention necessity for legal status, he found no alternative. His visibility on social media documenting immigration enforcement around Chicago provides glimpses into personal struggles. Guatemalan native Pascual experienced 82-day detention before habeas corpus release, charting an uncertain path with his first-ever work permit.

Jose, choosing anonymity, remains fearful after his 76-day detention during landscaping duties. His immense effort for release required $10,000 bond assistance from family and community, followed by lawyer fees—alongside awaiting work authorization and court suspension. He reflects desperation and hope amid legal uncertainty.

Cazares’ formal release averted immediate deportation, yet mentally, detention hell felt ongoing. As uncertainties shaped immigrant futures, released detainees faced trauma, anxiety, insomnia, and vigilance under hostile policies, observed Chicago therapist Lu Rocha. Misplaced fear like Jose’s McDonald’s hesitation reveals enduring stress. Backlogs and indefinite delays pervade, resulting in a broad legal purgatory exacerbated by systemic breakdowns, expressed by attorney Meinecke.

Cazares adopted hopes of a life with legal liberty, accumulating paperwork as protective amulets. The anxious anticipation of ever-elusive certainty persists amid perseverance for rightful residence.