SF judge says she was fired 48 hours after challenging ICE

Chloe Dillon was in the middle of deciding an asylum case at San Francisco’s immigration court when her supervisor told her to check her email.

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Dillon had finished hearing testimony and arguments and stepped back into her chambers to deliberate when she opened a termination notice. It was about 3:30 p.m. on Aug. 22, 2025. The letter said her removal was effective that day and ordered her to surrender her federal property. The notice cited only “Article II of the Constitution,” according to a lawsuit Dillon filed Thursday.

“I just started packing up all of my stuff,” Dillon told SFGATE by phone on Thursday. 

Her legal assistant was crying as colleagues helped take things off the walls and box up her belongings. Dillon’s husband drove from Berkeley with their 9-year-old son to load everything into the family Subaru. The firing also abruptly left Dillon, her husband and their two children without health insurance, she said. Dillon is the wife of SFGATE tech reporter Ramin Skibba, who joined SFGATE in 2026. 

The termination came roughly 48 hours after Dillon raised concerns with a supervisor about the detention of an unaccompanied minor asylum seeker who had appeared in her courtroom, according to her federal complaint.

On Aug. 20, 2025, the 18-year-old arrived early at the Montgomery Street courthouse alone, dressed in a suit and preparing paperwork before his case was called, Dillon recalled. An attorney for ICE then asked Dillon to dismiss the case so the government could pursue expedited removal proceedings, she said. Dillon instead gave the man a time period in which to find an attorney before ruling on ICE’s request. Before leaving, the asylum seeker asked whether he could be detained and whether he could still seek asylum, Dillon said.

“I said you could be detained at any point in time after this hearing,” Dillon recalled. She told him he still had the right to seek asylum and gave him a copy of his application.

Court staff later told Dillon that ICE agents detained him after he left the courtroom, the complaint says.

The detention unfolded amid a tense protest outside the Montgomery Street courthouse, Dillon recalled. Demonstrators tried to block federal officers from driving away with the teenager, who was escorted from the building in a suit with his hands restrained; protesters later followed officers toward ICE’s Sansome Street office, KQED reported. At least one person was detained and federal officers pepper-sprayed a protester and a journalist during the clashes, according to KQED.

Reviewing the case later that day, Dillon determined the man had entered the country alone at 17 and therefore was an unaccompanied minor, a status she believed barred expedited removal and required his asylum application to first be heard by U.S. Citizenship and Immigration Services. Dillon said she emailed then-Assistant Chief Immigration Judge Loi McCleskey that afternoon, raising concerns about possible violations of law and due process and saying courthouse arrests were disrupting the administration of justice.

“I said that I was concerned about this unlawful detention. I was concerned that these heavy-handed enforcement tactics were impeding the orderly administration of justice,” Dillon said. “And then it was only 48 hours later when I was fired.” 

Dillon alleges the Justice Department fired her in retaliation for reporting what she believed were violations of federal law and due process.
The August encounter was not Dillon’s first dispute with immigration court leadership, according to the lawsuit.

Months before her firing, McCleskey instructed San Francisco immigration judges to generally grant ICE requests to transfer cases and deny them only in “rare circumstances,” according to the complaint. Dillon said ICE lawyers were frequently pushing to move cases out of San Francisco to distant courts in other parts of California or even out of state. Dillon argued judges retained discretion to make those changes and that transfers could burden attorneys, witnesses and respondents’ access to counsel. 

Dillon said McCleskey later cautioned her that “the White House” was paying attention to the issue. She told SFGATE Thursday she did not view the warning as a threat. 

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“She was cautioning me,” Dillon said. “Essentially, like, do you really want to push this?”

Dillon later denied ICE requests to move at least some cases when attorneys objected. The lawsuit alleges that court administrators subsequently transferred one such case anyway.

Her lawsuit, filed Thursday in the Northern District of California, accuses the Justice Department of violating the Whistleblower Protection Act, the First and Fifth amendments and federal administrative law. Dillon is seeking reinstatement, back pay, damages and a declaration that her firing was unlawful. 

The complaint alleges she received no notice or opportunity to challenge the dismissal before it took effect. Dillon served as a San Francisco immigration judge from 2022 to 2025 within the Justice Department’s Executive Office for Immigration Review and now works as a public defender in San Mateo.

Dillon first appealed her firing to the Merit Systems Protection Board, according to her complaint, which says the case has remained unresolved for about a year as the board weighs related litigation involving other fired immigration judges. That delay prompted her to take the dispute to federal court.

“If you do something even small that they don’t like, they’re gonna fire you,” Dillon said. She described the climate around the firings as a “hair trigger.”

By the time Dillon was fired, San Francisco’s immigration court was already being hollowed out. Seven judges were dismissed in a matter of months, including Assistant Chief Immigration Judge Loi McCleskey, while more than 120,000 cases remained pending before the court, according to SFGATE’s previous reporting in September 2025.

The losses came amid a broader contraction of the immigration bench. The Justice Department began 2025 with more than 700 immigration judges nationwide. By that September, fewer than 600 reportedly remained. EOIR also moved to close the San Francisco court, ending hearings at its Montgomery Street location and permanently shuttering the court on Sept. 4. Its cases were reassigned to the Concord Immigration Court.

“When you have judges who are in fear that they will be fired for the decisions that they’re making, it has completely undermined the basic principles of judicial adjudication,” Dillon said. “I don’t see how you have fair and unbiased tribunals in the immigration court when there is this atmosphere of fear and intimidation.”

Her lawsuit alleges she experienced that pressure firsthand, arguing that she was fired after questioning government practices she believed violated federal law. The Justice Department has not yet responded to those allegations in court. SFGATE reached out to the Department of Justice but did not hear back prior to publication.

“I hope that this story of what happened to me will help shed a light on what is happening in the immigration courts,” Dillon said. “These are cases that mean a lot to the people who are there, both them and their surrounding communities, and they at least deserve a fair shake.”