Meeting the Moment

On Jan. 10, Maria Loya Medina was driving to a Big 5 Sporting Goods store near her home in Albany to buy socks for her son for an upcoming soccer match. A house cleaner with two children, Medina is also the primary caretaker for her husband, who suffered a stroke in 2025. She’s lived in the U.S. for 21 years, and Oregon for nearly 10.

In the store parking lot, agents from Immigration and Customs Enforcement (ICE) suddenly swarmed her car, smashed her windshield and dragged her into custody without a warrant. Despite the fact that her husband was scheduled to have heart surgery several days later, Medina was sent to an ICE detention center in Tacoma, Washington. She’s been there ever since.

Medina’s arrest was one of more than 1,000 that occurred in Oregon in the last year as part of the Trump administration’s mass-deportation campaign dubbed “Operation Black Rose.”

“Everything is so fragile right now,” says Portland immigration attorney Stephen Manning, founder of Innovation Law Lab, an advocacy organization that has filed scores of lawsuits on behalf of immigrants—including a habeas corpus petition in Medina’s case.

Though Manning girded himself for the second Trump administration, having been around for the first, its disregard for basic standards of law shocked even him. “This time around, it feels violent, it feels dangerous,” he says. “Dangerous on a constitutional level, on civic society level, on a personal level, and in the community. On each of those levels, the pulse rate is high. The stakes are gargantuan. The room for error is zero.”

Philip Smith, an immigration attorney for 25 years, has never seen anything like it. “Following the law takes time, and people have rights, and hearings need to be scheduled,” he says. “What has driven this is a policy to remove as many people as you can as quickly as you can.”

“The agents aren’t trained in the law,” Manning adds. “They’re trained on tactics: ‘This is how you take someone down. That’s how you shatter a window.’”

Throughout, many attorneys have worked long hours to defend immigrants and stand up for the rule of law. “It’s an honor to be an attorney in this moment,” says Kelly Simon, legal director of the ACLU of Oregon. “It’s critical that we continue to get these cases into our courts—and we need as many of us as possible doing that right now. Judges still have the power of judges. We are not in a scenario where that power is gone.”

“We know we were targeted because of our sanctuary laws. We know we’re targeted because of our healthy protest culture here.”

‘War-Ravaged’

Last September, as protests took place at the ICE processing facility in Portland’s South Waterfront district, President Trump ordered a surge in immigration enforcement while attempting to gain federal control of the Oregon National Guard—as he had done earlier in California. When Oregon Attorney General Dan Rayfield filed a lawsuit to block that federalization, Trump ratcheted up the rhetoric, saying, “Portland is burning to the ground,” “Portland’s been on fire for years,” and “You don’t even have stores anymore. They don’t even put glass up. They put plywood on their windows.” He called the city “war-ravaged.”

On the streets, the federal presence was often met with whimsy, as activists turned up wearing inflatable frog, cow and dinosaur costumes. In October, then-chief of the Department of Homeland Security (DHS), Kristi Noem, stood on the roof of the ICE facility and viewed the protests, which included a man in a chicken suit. Affectionately dubbed “the Portland Chicken,” Jack Dickinson has been a regular fixture at the confrontations on Macadam Avenue, but after being subjected to several tear gas exposures he sued the feds with the help of the ACLU. The case, Dickinson (aka “the Portland Chicken”) v. Trump, is ongoing.
“We know we were targeted because of our sanctuary laws,” says Ashlee Albies, a civil rights attorney at Albies & Stark in Portland, who’s worked closely with the ACLU of Oregon to defend the rights of protesters. “We know we’re targeted because of our healthy protest culture here.”

In October, Innovation Law Lab filed a lawsuit, M-J-M-A- v. Wamsley, demanding a halt to ICE’s practice of conducting warrantless immigration arrests in Oregon; its named plaintiff was arrested without a warrant in Woodburn, where 60% of the population is Latino. Court records later revealed that ICE teams, with a quota of eight arrests per day, used surveillance technology to create target areas where immigrants were likely to be found.

“That’s one of the primary grievances that caused the Revolutionary War and led to the Declaration of Independence—the writ of assistance,” Manning says. King George III, attempting to root out American resisters, simply issued a blanket order to his agents. “He would say, ‘Here’s a writ, go find me people who are fighting their taxes. Just search their homes. Go search everybody’s home. You’ll find somebody.’ That’s what they’re doing now with surveillance.”

John Marandas, an immigration attorney at Marandas Garcia Law Group in Lake Oswego, says his firm has seen a huge uptick in requests for representation—with matters becoming more convoluted and outcomes more unsure. Immigrants who arrived in the U.S. as children or refugees, and who have an old conviction on their record, are suddenly at risk of deportation even if they’ve lived here for decades.

It’s hard to offer legal advice, Marandas adds, when the administration constantly shifts its policies and tactics. “Based on anecdotal evidence of what’s happening to other folks,” Marandas says, “we can say to some clients: You’re a very high risk for being arrested at your ICE check-in, being taken to Tacoma, and removed either to your home country or a third country.”

“This time around, it feels violent, it feels dangerous. Dangerous on a constitutional level, on a civic society level, on a personal level, and in the community.”

Taken to Tacoma

Because the contract at Portland’s ICE facility does not allow for overnight stays, ICE and DHS have taken to rushing people held in detention across the Oregon-Washington border by bus, while, at the same time, immigration attorneys scramble to file habeas petitions to secure their release before they’re moved out of state.

Philip Smith and his law partner Nicole Nelson have become adept at this—relying on a network of volunteer legal observers or existing clients who let them know when someone is taken into custody.

“It’s so rushed and in the moment,” says Nelson. “One of us is trying to prepare the habeas petition while another one is preparing the motion for a TRO and trying to put together the exhibits to prove the facts that we’re stating—getting the documentation ready to file online before they’re taken across the border.”

In one instance, a construction worker from Guatemala, married to a U.S. citizen, was in the process of getting his green card; but as he drove to Home Depot to pick up supplies, ICE agents surrounded and detained him. “We were able to file that one in time,” Nelson says. “They actually had to stop the bus and send another car and get him off the bus before it got to Vancouver.”

One of Marandas’ clients had received an employment authorization based on a pending U visa—granted to crime victims who have suffered harm and been helpful to U.S. law enforcement. He wound up in Tacoma. “For ICE to pick up and arrest someone who had been granted deferred action was very inconsistent and illegal,” says Marandas, who worked with colleagues in Washington to force his release.

Cross-state transfers generally complicate matters. Not every attorney has the resources to practice in multiple states, and immigrants are often put on flights to other detention centers and can get lost in the system. Even if they aren’t, conditions are so bad at the ICE processing center in Tacoma, from which state health inspectors have been repeatedly barred, that those held there for an extended period often elect to self-deport.

“It is soul-crushing to be detained,” Smith says. “They quickly go downhill, mentally and emotionally. The first day or two after they’ve been detained, they’re fired up, they want to fight their case. A week later, they’re really worried. After two or three weeks, they just want to sign the papers and leave.”

Nelson says she encourages her clients to talk on the phone with her even if the call isn’t confidential, just to assure them that work is being done and not to lose hope. Caroline Keating Medeiros, who works at Marandas’ firm, recalls one Chinese client held in Tacoma who is legally blind and has serious health conditions, so she filed a habeas petition based on lack of medical care. “Unfortunately, the judge took too long, and my client had already decided to accept his order of removal,” Medeiros says.

That’s assuming attorneys even have access to clients. Portland attorney Leni Tupper, a founder of CLEAR Clinic, a legal assistance organization involved in deportation defense, says she and colleagues have repeatedly observed ICE officers refusing attorney requests to speak with detainees, including some detainees who hold U.S. citizenship.

Tupper says one of CLEAR’s attorneys tried to speak with a detained client who had Temporary Protected Status (TPS). The ICE officer responded: “TPS, I don’t even know what that is—Third Party Spaghetti?” Another time, a CLEAR clinic attorney asked to speak to a client, a military veteran who was being detained at the Macadam facility, but she was told the facility was closed because of Veterans Day. “The irony was not lost on us,” Tupper says.

A class action lawsuit, CLEAR Clinic v. Noem, filed last October with Innovation Law Lab, has challenged DHS’s practice of denying detainees the basic right to legal counsel.

“For ICE to pick up and arrest someone who had been granted deferred action was very inconsistent and illegal.”

Down on Macadam Avenue

This spring, as Operation Black Rose was winding down, the scene on Macadam Avenue in South Waterfront felt surreal. Amid glistening apartment buildings, and people biking along the Willamette River, the fortress-like ICE processing facility, covered in surveillance cameras, its windows protected by plywood and its roof lined with razor wire, was the only thing in the neighborhood that looked war-ravaged. Everything else was serene.

Innovation Law Lab’s Justice Bus, a mobile legal clinic, is a frequent presence in the neighborhood. Manning is often there, helping immigrants prior to their appointments; tracking down detainees; and assisting them by firing off another habeas petition. In addition to responding on-site to ICE arrests, the van travels the region as a venue for legal rights clinics.

CLEAR Clinic, with offices nearby, started at Portland Community College in 2020 to provide paralegal students with experience in economic justice law and immigrant defense work. It has now grown to a statewide nonprofit thanks in part to Equity Corps of Oregon (ECO), a unique program that began in Portland and Multnomah County in 2018 and was expanded statewide by the legislature in 2022. The ECO program guarantees free legal counsel to all immigrants facing wrongful deportation, and has provided free representation to more than 12,000 clients.

“It would be impossible for us to do as much … without Equity Corps of Oregon,” Marandas says. “Often, our clients don’t have the resources to assist them in their immigration cases that involve so much time and effort.”

In February, the ACLU of Oregon obtained a temporary restraining order preventing ICE from using tear gas on protesters unless they presented an “imminent threat of physical harm.” A second lawsuit, filed by residents of the Gray’s Landing affordable housing apartment building across the street from the ICE facility, also obtained a TRO against tear-gas usage. But in April, a judge ruled against the residents, stating there was no constitutional right to be free from exposure to tear gas.

Even the Portland Police Bureau, Albies says, with its heavy use of tear gas against protesters in 2020, testified in the ACLU case against such usage by ICE. “They said, ‘Oh no, there’s a process you should use before you use tear gas,’” Albies says. “‘These things are very basic. You give people notice, give clear warnings that you’re about to use these weapons. And you give people the opportunity to disperse.’”
ICE’s tactics against protesters, Albies adds, are designed to spread fear. “We have seen this administration also attack lawyers and law firms that oppose it or resist it,” Albies says. “It seeks to create a culture of fear and a culture of hesitation.”

Whitney Phelps, the immigration justice program director with CLEAR Clinic, says her staff works to support each other. “We’re doing as well as can be expected,” Phelps says. “It’s chaotic. Every day feels like a new horror.”

To protect his own mental health, Manning refrains from watching the news. His husband had to inform him when the U.S. attacked Venezuela and kidnapped its president: “I was like, ‘Oh yeah, I need to know that,’” Manning recalls.

The Trump administration’s actions in Portland, and in cities like Minneapolis, have shaken Manning’s confidence in the rule of law itself. “I really thought there was this exceptionalism about the U.S. experiment—that it was unique,” he says. “I thought our Constitution was pretty cool, and the way we set it up, and look how long we’ve lasted. But there are structural things happening that are going to make it really hard for us to come back.”

“One of us is trying to prepare the habeas petition while another one is preparing the motion for a TRO and trying to put together the exhibits to prove the facts that we’re stating.”

The Moment

There are slivers of hope. Nelson talks up protesters and residents delivering groceries to neighbors in hiding. “When I go down to the ICE building, I’ll see a nice middle-aged woman in a vest that says ‘VOLUNTEER,’” Nelson says. “She has a card table set up. She has these little ‘Know Your Rights’ pamphlets she’s printed herself.”

Last fall, Rayfield was successful in preventing the nationalization of the Oregon National Guard before the 9th Circuit, and in February U.S. District Judge Mustafa T. Kasubhai granted a preliminary injunction in Innovation Law Lab’s M-J-M-A- class action lawsuit, ordering ICE to stop its “arrest first, justify later” practices in Oregon. He noted that the agency’s “warrantless arrests without individualized determinations of flight risk” violated U.S. immigration law.

“That was a huge, enormous breath of fresh air,” Manning says. “Now people can be like: OK, I think taking my kid to school is not an existential threat.”

He’s quick to point out it’s only a temporary reprieve that might be overturned.

Manning often works with Nelson, Smith, Tupper, and Phelps, along with many, many others, and is proud to be fighting alongside them. “It’s an amazing crew of attorneys. They’re good people, doing really great work,” he says. “I mean, this is why I went to law school, right? This is why I got the degree. If you’re going to meet the moment—well, this is the moment.”

“Following the law takes time, and people have rights, and hearings need to be scheduled. What has driven this is a policy to remove as many people as you can as quickly as you can.”