A former immigration judge based in San Francisco has filed a federal whistleblower lawsuit against the United States Department of Justice, alleging she was abruptly terminated in retaliation for challenging the detention of a teenage asylum seeker by federal immigration officers. Chloe Dillon claims her swift dismissal came roughly 48 hours after she formally raised constitutional and procedural objections regarding the enforcement actions of U.S. Immigration and Customs Enforcement.
According to the complaint filed in federal court, Dillon was actively deliberating an asylum matter at the San Francisco immigration court on Montgomery Street on the afternoon of August 22, 2025, when the sudden firing occurred. Dillon had just finished hearing legal arguments and witness testimony before returning to her judicial chambers. At approximately 3:30 p.m., a supervisor instructed her to check her email inbox, where she discovered an official notice of immediate removal.
The termination document provided minimal explanation for the sudden action, citing only Article II of the United States Constitution as the authority for her dismissal. The correspondence instructed Dillon that her employment was being terminated effective that very afternoon and directed her to immediately surrender all government-issued property in her possession.
The abrupt firing created an emotional scene inside the courthouse chambers as staff members reacted with disbelief. Dillon recalled that her legal assistant broke down in tears while colleagues stepped in to help take down personal items from the walls and pack her office belongings into boxes. Her husband had to drive from their Berkeley residence alongside their 9-year-old son in the family vehicle to help load and transport her personal effects from the judicial building.
Beyond the professional shock, the sudden firing carried immediate domestic and financial repercussions for Dillon and her household. The dismissal instantly stripped Dillon, her husband, and their two children of their family medical coverage. Dillon is married to technology journalist Ramin Skibba, who joined the SFGATE newsroom the following year in 2026.
According to the legal filing, the dismissal was the direct culmination of an incident that began two days earlier, on August 20, 2025. That morning, an 18-year-old asylum seeker arrived unaccompanied at the Montgomery Street federal courthouse. Dillon observed the young man sitting alone in a suit, meticulously organizing his paperwork before his scheduled hearing was formally called before the bench.
During the courtroom proceeding, a government attorney representing ICE formally petitioned Dillon to dismiss the ongoing immigration court case. The government's stated objective was to release jurisdiction so that immigration authorities could pursue an expedited removal process against the young migrant. Rather than granting the government's motion on the spot, Dillon opted to postpone a final determination, granting the young respondent an allotted window of time to retain legal representation.
Before departing the courtroom, the young asylum seeker asked the judge whether he was at risk of apprehension by federal authorities and whether his asylum pursuit could still move forward. Dillon recalled informing the teenager that detention remained a possibility at any time once he exited the proceeding, while reaffirming his legal entitlement to seek asylum and furnishing him with a physical copy of his application documents.
Shortly after the teenager left the courtroom, court personnel informed Dillon that ICE agents had intercepted and detained the young man inside the building. The arrest immediately sparked significant unrest outside the Montgomery Street facility, where demonstrators had gathered to protest enforcement actions taking place at the courthouse.
Tensions escalated as protesters attempted to physically block federal vehicles from transporting the restrained teenager away from the facility. The confrontation continued as demonstrators trailed federal agents toward ICE offices located on Sansome Street. The resulting clash saw federal officers deploy pepper spray against at least one demonstrator and a reporting journalist, while at least one individual was taken into custody.
Following the hearing, Dillon conducted a deeper review of the case record and determined that the respondent had initially entered the United States on his own at the age of 17. Because of his entry as an unaccompanied minor, Dillon concluded that statutory safeguards shielded him from expedited removal and mandated that his initial asylum petition be evaluated by U.S. Citizenship and Immigration Services rather than bypassed through immediate deportation channels.
Disturbed by the procedural anomalies, Dillon composed an email that afternoon to then-Assistant Chief Immigration Judge Loi McCleskey. In her message, Dillon warned that the teenager's apprehension represented a potentially unlawful detention and raised serious due process red flags, arguing that aggressive enforcement within courthouse corridors was actively undermining the administration of justice.
Dillon expressed direct concern that these aggressive enforcement practices were obstructing the normal functions of the legal system, only to receive her termination notice two days later. The whistleblower lawsuit maintains that the Department of Justice removed Dillon as an unlawful act of retaliation for exposing what she reasonably considered to be statutory breaches and due process violations. The complaint also indicates that the August confrontation was part of a broader history of tension between Dillon and immigration court leadership over administrative practices.
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