Jessica, a 33-year-old special education teacher at a local private school, was sitting damp-eyed on a stoop near immigration court at 26 Federal Plaza.

Her husband, Jean Carlos, had come Monday morning for a hearing in his asylum case, and Jessica, feeling a growing sense of unease, had decided to accompany him.

The two exchanged WhatsApp messages throughout the morning while Jessica waited outside in a nearby park. But when THE CITY encountered Jessica on that afternoon, it had been hours since she’d heard from him.

“I don’t even want to get up,” Jessica said. “I feel like I’m leaving him here.”

Jessica, a U.S. citizen who was born and raised in Jamaica, Queens to Ecuadorian parents, has a two-year-old daughter with Jean Carlos, who’s also 33 and just arrived from Ecuador last year. The family is one of many whose have been separated this week by ICE agents as they round up immigrants leaving routine court appearances in Lower Manhattan immigration courthouses as part of the Trump istration push to massively increase the number of deportations. 

Those arrests, along with others at people waiting anxiously for their loved ones to return from a scheduled visit, with many dazed and teary-eyed after losing with someone who entered an immigration proceeding and never returned. 

Late Monday morning, Jean Carlos’s messages to Jessica shifted from ordinary to urgent. 

“Ahh, so many ICE police, I hope nothing happens,” he wrote in Spanish at 11:04, according to WhatsApp messages shared with THE CITY.

“Don’t scare me like that,” she wrote back a minute later. 

“They’re outside of the room,” he responded. 

‘Amazed by All the Lights’

Jessica often spent summer vacations in Ecuador, visiting extended family in the seaside city of Manta, where her mother is originally from. On one such visit in 2020, she met Jean Carlos at a family quinceañera. Both Jessica and Jean Carlos have two sons from previous relationships, and the tenderness he showed his own kids and hers  caught her eye right away.

THE CITY is withholding both of their full names due to the precarity of Jean Carlos’s immigration case.

The relationship continued long-distance, with summers spent together in Ecuador. “He was funny. We liked the same music. I like the beach. He likes to surf. He likes adrenaline,” she said. The two were an easy match. 

They got married in Ecuador in 2021 and started the paperwork for a spousal visa so they could be reunited in New York City. Three years later, still maintaining the long-distance relationship, Jessica gave birth to a baby girl. 

“I gave birth alone. He was like, ‘I promise you I’ll be here for her first birthday,’” she recalled. 

While Jean Carlos continued waiting for his spousal visa, he faced mounting threats from gangs shaking him down for a cut of the money he made as a street vendor selling hamburgers. Finally, he decided to take his chances and make his way to the United States border. En route he was robbed multiple times, kidnapped and broke his foot. But by the spring of 2024 he made it across the border on crutches. 

The couple had a happy reunion in New York City, a few weeks before their daughter’s second birthday, and Jessica got to see the city she’d grown up in with new eyes when she took Jean to ride the Staten Island Ferry and visit Times Square. 

“He was amazed by all the lights,” Jessica said, reminiscing about how Jean Carlos once exclaimed, “‘This is what I see in the movies!’”

“Me as a New Yorker, I don’t like being where there’s a lot of people, but I was a tourist with him,” Jessica recalled. This summer, the two planned to go on a horse-drawn carriage ride in Central Park and ride on a double-decker bus, things she always thought were corny. 

Jean Carlos, working odd construction jobs, was on edge that immigration enforcement might show up at any given job site, Jessica said. He applied for asylum and had his fingerprints taken as part of the process, continuing to work through the proper channels. Even as rumours spread on TikTok of courthouse arrests, he was determined to show up. 

On Monday, Jessica called out of work to head to court with him. The two left their Queens apartment in the early morning, saying goodbye to their 2-year-old daughter, who they left with a caretaker.

“It was like he knew,” Jessica said. “He hugged her this morning [and said], ‘If I don’t see you later, Mommy’s coming back.’”

“I was like, ‘Don’t say stuff like that.’”

‘A Farce Already’

Jessica and Jean Carlos arrived at the lower Manhattan courthouse just as the Trump istration was pushing to vastly expand the use of “expedited removal,” which it says allows them to end court proceedings and rapidly remove anyone who has been in the country for less than two years.

That’s part of an ongoing effort to massively increase the number of arrests, and deportations, nationwide — a move that necessarily means targeting people with no criminal histories. This Tuesday, the agency made 2,200 arrests nationwide, according to NBC News, its record for a single day.  

That push has hit lower Manhattan hard, with ICE agents using three adjacent immigration courthouses as well as offices where immigrants report for required check-ins to make dozens of arrests this week. 

Inside courtrooms. THE CITY has at the request of government lawyers.

Immediately after those cases were dropped, some immigrants were arrested just outside of their courtrooms by federal agents, many wearing masks. 

The Department of Homeland Security said earlier this week that its agents often wear face coverings to “protect themselves from being targeted by known and suspected gang , murderers and rapists.”

When the mass arrests inside the court building began this Monday, ICE agents huddled together in the lobby to grab people exiting elevators. 

Later in the week, as more reporters and activists began showing up to document the detentions, ICE agents moved from the lobbies up onto the floors of immigration court, lurking in the hallways to grab people as they exited hearings and escort them to the freight elevator.

Earlier this week, THE CITY saw one judge offer several people 30-day extensions so that they could research the government’s moves to toss their cases. But even after attorneys informed ICE officers that their clients’ cases were still ongoing, the people were outside the courtroom. 

Andrés Santamaria, an attorney with the immigrant-led advocacy group Make the Road New York, said he’d witnessed some cases where an immigration judge denied the government’s motion to dismiss outright — but people were still detained after exiting courtrooms nonetheless.

Santamaria said the situation highlights how little power immigration judges, who are executive branch employees of the Department of Homeland Security rather than of the judiciary, really have. 

“This whole thing is a farce already,” said Santamaria. “Anyone who is here two years [or less] is at risk of this,” he said. 

‘They’re Taking People’

After ICE agents first showed up outside the courtroom Jean Carlos was in, he and Jessica continued messaging back and forth. At 12:46, just over an hour and a half after he’d first told her about the ICE police, as he called them, outside the courtroom door, the arrests began.

“They’re taking people. Love. What the fuck,” he wrote. 

“What are you talking about, love, what did they say.”

Jean Carlos had time to make a quick video call, telling Jessica he loved her and their daughter, and snapping photos of his immigration court paperwork. 

They show that his judge hadn’t allowed the government’s request to dismiss his asylum case, and he was due back in court in June of 2026. 

Then Jessica stopped hearing from him. 

Hours later, she was still sitting on a stoop a few blocks away, eyes damp with tears, uncertain what had happened to her husband and debating what she should do next. Attorneys who were present at 26 Federal Plaza later confirmed to her he had been detained.

“How do you expect people to do things the right way if you’re going go arrest them like this,” she wondered. “How do I go back home now and look at my daughter?”