NEW YORK — In a direct challenge to the judiciary and a deepening constitutional crisis, federal immigration agents have taken three men into custody at New York City immigration courts over the past week. Legal advocates and civil rights organizations argue that these actions constitute a brazen violation of explicit federal court orders that strictly limit, and in many instances prohibit, enforcement operations at judicial facilities. The arrests—targeting immigrants from Ecuador, the Dominican Republic, and Guatemala—have sparked a firestorm of legal and political protest, with critics characterizing the actions as a descent into lawlessness that threatens the integrity of the American judicial system. The Chronology of the Detentions The recent string of detentions began on Thursday, when agents from U.S. Immigration and Customs Enforcement (ICE) conducted two separate operations in Lower Manhattan. An Ecuadorian national was apprehended at the immigration court located at 26 Federal Plaza, while a man from the Dominican Republic was detained at the 290 Broadway courthouse. The enforcement activity did not cease with the week’s end. On Monday, ICE agents returned to the 290 Broadway facility, taking a third man—originally from Guatemala—into custody. Unlike previous instances where immediate advocacy led to the release of individuals detained in violation of court protocols, these three men have been processed through the system and transferred to far-flung detention centers. According to agency records, the Dominican man is currently being held at the Delaney Hall detention facility in Newark, New Jersey. The Ecuadorian national was transported to the D. Ray James ICE Processing Center in Folkston, Georgia, while the Guatemalan detainee is being held at the Orange County Detention Facility in upstate New York. A Legal Framework Under Siege The current enforcement surge follows a pivotal May 18 ruling by U.S. District Judge Kevin Castel. That order mandated that ICE revert to a 2021 policy governing courthouse arrests. Under those guidelines, enforcement operations at judicial buildings are permitted only in the most narrow of circumstances: when a specific individual poses a significant national security threat or a clear danger to public safety. Furthermore, even in those cases, the policy requires that agents prove the arrest could not have been executed safely in a non-judicial location. This New York-specific mandate is bolstered by a broader, nationwide ruling issued on June 23 by a federal court in California, which similarly restricts the ability of federal agents to treat courthouses as hunting grounds for undocumented immigrants. Advocacy group Make the Road New York has filed multiple habeas corpus petitions, arguing that the recent detentions are not merely procedural errors but intentional violations of federal law. Lawyers for the organization are demanding the immediate release of the detainees, arguing that their clients were in full compliance with the law—having arrived at their scheduled hearings as required—only to be intercepted by agents. Official Responses and Justifications The response from federal authorities has been characterized by a notable lack of transparency. When reached for comment, an ICE spokesperson categorically denied that the agency had violated any court orders. However, the agency stopped short of explaining how these specific arrests met the stringent "public safety" or "national security" exceptions established by Judge Castel’s order. When pressed on the specific grounds for the arrests, the spokesperson pointed to past criminal records: a trespassing conviction for the Dominican national and a 2025 conviction for disorderly conduct for the Ecuadorian man. Legal experts, however, contend that these minor, past infractions do not meet the legal threshold of a "threat to public safety" that would justify an exception to the courthouse arrest ban. The lack of a clear, legal justification has invited harsh rebukes from federal lawmakers. Rep. Dan Goldman (D-N.Y.) issued a scathing statement condemning the agency’s behavior. "ICE continues to flagrantly violate the law by arresting immigrants who are attending their mandatory court hearings, despite a court order mandating an end to courthouse arrests," Goldman stated. His office is currently coordinating with legal teams to seek the release of the three men. The Atmosphere of "Lawless" Enforcement For those working within the immigration court system, the recent arrests represent a broader, systemic failure of accountability. Murad Awawdeh, executive director of the New York Immigration Coalition, did not mince words when describing the agency’s current posture. "We’re witnessing ICE, yet again, operate in a lawless and rogue fashion and not following court orders," Awawdeh said. "We’re supposedly a nation under the rule of law, and our judicial branch has said that this agency must stop engaging in this lawless behavior, yet they continue to do so. It is an affront to the judicial branch and to the rights of the individuals involved." Benjamin Remy, a senior coordinating attorney at the New York Legal Assistance Group, noted that these events are not isolated incidents but part of a calculated shift. "For whatever reason, that order is essentially being disregarded, and we’ve seen a pretty significant uptick in detentions," Remy observed. "We’ve seen ICE have a fairly flexible and adaptive relationship when it comes to the truth and the facts, and to complying with court orders and, frankly, the rule of law as a fundamental concept." Implications for the Immigration Process The chilling effect of these arrests on the immigration system cannot be overstated. Since the inauguration of President Trump and the subsequent rollout of a mass deportation agenda, the relationship between immigrant communities and the legal system has become increasingly fraught. Between May 2025 and May 2026, New York City became the epicenter of courthouse enforcement, with data from local reports indicating that more than half of all national courthouse arrests occurred at NYC facilities. Many of these arrests were carried out by masked agents, creating an environment of fear that deterred thousands of people from attending their hearings—thereby effectively sabotaging their own legal claims for asylum or status adjustment. The "impossible bind" created by these policies is a central point of contention for immigration lawyers. Immigrants are forced to choose between two equally devastating options: skip their court dates, which leads to an automatic in absentia order of deportation, or attend their hearings, which makes them vulnerable to arrest by ICE agents waiting in the lobby or hallways. "It is not uncommon for me to encounter folks walking into court in the morning already just sobbing," Remy told reporters. "These arrests are discouraging the legal process. It is discouraging people’s fundamental constitutional right to due process and to be able to have their day in court." A Pattern of Judicial Friction The current situation is reflective of a wider trend observed over the past year and a half. As the federal government has ramped up its deportation apparatus, instances of judicial frustration have grown. Across the country, judges in Iowa, California, and New York have issued stinging rebukes of the agency, citing "astonishing conduct" and "disregard for the rule of law." The escalation in recent months suggests that ICE is operating with a level of autonomy that has effectively bypassed the oversight of the federal judiciary. For advocates, the question is no longer just about the rights of the three men detained this week, but about the ability of the judiciary to enforce its own mandates against an executive branch agency that appears increasingly indifferent to the constraints of the law. As legal challenges continue to move through the courts, the fate of the three men remains uncertain. For now, they remain behind bars in separate states—a testament to the ongoing power struggle between the federal government’s deportation machinery and the constitutional protections that are meant to govern it. Whether the courts will move to hold the agency in contempt or find another mechanism to enforce their orders remains the primary focus of civil rights litigators in the coming weeks. Post navigation The Weaponization of Oversight: Inside the HHS-CAIR Controversy The New Execution Era: Inside the Trump Administration’s Aggressive Capital Prosecution Push