Unconventional Judge Is Managing Trump’s Court Deportation Blitz

The Trump administration’s deportation agenda is getting pivotal support from a lesser-known official managing the more than 600 immigration judges deciding migrants’ fates.

As chief immigration judge, Teresa Riley oversees the Justice Department’s immigration courts as they hear cases of migrants swept up in President Donald Trump’s crackdown.

In her role, Riley has issued directives that advance the agenda set above by Trump, Stephen Miller, and other administration leaders, according to former officials and analysts. The changes make it increasingly difficult for immigrants to obtain asylum and avoid deportation, observers said.

Riley, a former federal prosecutor appointed chief judge in December after roughly two months in an acting capacity, has less managerial experience than many of her predecessors. She’s also carrying out the role in an unconventional way.

Riley is encouraging judges to refrain from granting asylum in most cases and telling them they’re not required to hold bond hearings despite federal judges’ declarations that noncitizens are entitled to argue for their release. Immigration judges, dubbed “deportation” judges in recent DOJ recruitment ads, are department employees with limited discretion and little of the autonomy of life-tenured judges.

“When you take a step back and look at how all of this works together, the more people are detained, the harder it is for them to access counsel, the harder it is for them to be able to apply for and win relief,” said Kathleen Bush-Joseph, a US immigration policy analyst with the Migration Policy Institute.

Riley, who joined the Cleveland Immigration Court in 2019, was sent for additional training after a 2021 complaint submitted by the American Immigration Lawyers Association’s Ohio chapter alleged she engaged in “bullying” and “hostile questioning” of migrants.

She’s now part of leadership at DOJ’s Executive Office for Immigration Review advising judges to deny most asylum claims and issue deportation orders, according to former officials and policy analysts. EOIR leaders have fired more than 100 immigration judges, fast-tracked cases, and moved to cut off a key avenue for migrants challenging deportation orders.

EOIR Director Daren Margolin called Riley “a highly qualified adjudicator and senior leader, who is effectively implementing the administration’s plan to enforce the immigration laws of the United States, as passed by Congress.”

“After four years of the Biden Administration forcing immigration courts to implement a de facto amnesty for hundreds of thousands of aliens, this Department of Justice is restoring integrity to our immigration system,” Margolin said in an emailed statement.

EOIR declined to make Riley available for an interview.

Chief Judge

As chief judge, Riley’s directives go beyond her job description, former EOIR officials said.

Under federal regulations, the chief immigration judge may issue operational instructions and policy, including time frames for judges to resolve cases and managing judges’ dockets. The chief judge doesn’t have authority to “direct the result of an adjudication assigned to another immigration judge,” according to the regulations.

Riley’s January guidance directing immigration judges they weren’t bound by a federal district judge’s ruling that noncitizens should be given bond hearings improperly interferes with “the impartiality that immigration judges should have,” said Margy O’Herron, an immigration adviser during the Biden administration and former Board of Immigration Appeals attorney.

“The chief immigration judge is supposed to oversee the management functions of the immigration courts, not put a thumb on the scale that affects the outcome of adjudications,” O’Herron said.

Riley stood by the Trump administration’s stance on mandatory detention after a California federal judge on Feb. 18 overturned a BIA precedent that Riley relied on in her January guidance.

Riley wrote in new guidance to immigration judges that the Feb. 18 ruling doesn’t vacate or overrule the Fifth Circuit’s recent decision upholding the administration’s interpretation of mandatory detention. The Ninth Circuit has since paused the California judge’s order.

Prior chief judges didn’t issue this type of guidance, and it wouldn’t have made it past the EOIR director or general counsel’s office in earlier administrations, according to one former immigration judge who requested anonymity to speak openly about previous decision-making.

O’Herron described the guidance similarly, noting it’s “very inconsistent with the way past leaders at EOIR across the six administrations that I worked in operated.”

But Matt O’Brien, deputy executive director of the conservative Federation for American Immigration Reform, said in an email that Riley’s guidance was “both appropriate and necessary.” Federal district court judges don’t have authority to order immigration judges to hold bond hearings, he said.

“The mere fact that the guidance given by Chief Immigration Judge Riley may be different than that issued by her predecessors is in no way an indication that her guidance is wrong,” said O’Brien, a former assistant chief immigration judge overseeing the court in Annandale, Va.

An EOIR spokesperson said in an email that the Trump administration “is complying with court orders and fully enforcing federal immigration law.”

“The level of illegal aliens currently detained is a direct result of this Administration’s strong border security policies to keep the American people safe,” the spokesperson said.

Interactive graphic: Teresa Riley has less immigration experience than prior chief judges

Courtroom Demeanor

Before she quickly ascended to the chief judge role, Riley stood out from other judges early on in her time at the Cleveland Immigration Court for comments to immigrants that attorneys characterized as inappropriate from someone required by law to be an impartial adjudicator.

AILA said in its 2021 complaint that, in at least one case in 2020, Riley referred to undocumented immigrants as “illegals.” AILA alleged that in another hearing, Riley questioned whether a migrant was being truthful about sexual abuse his daughter experienced because the man displayed “no emotion whatsoever.”

“Can you explain to me why you’re rattling this off like you’re reading the newspaper?” Riley asked the father, according to a copy of the complaint obtained by Bloomberg Law.

Maureen DeVito, who worked as an immigration attorney in Cleveland from 2019 to 2025, said the AILA complaint shows “very cruel statements” that align with her own experience.

At a 2019 hearing, DeVito represented a 9-year-old Guatemalan migrant who started crying after Riley “made callous comments” telling the girl she could be deported even though, DeVito said, “this child had no agency or authority over the actions of her parent.”

Riley had no visible reaction to the child’s emotion, said DeVito, who noted that others in the room “had astonished looks on their faces.”

“She just continued on, traumatizing the child even further,” DeVito said of Riley. “I’d never seen a judge terrify a child like this before.”

EOIR, which oversees immigration courts, closed AILA’s complaint after sending Riley for two weeks of training in 2021 on her tone and interactions with migrants who appear without an attorney, according to two people familiar with Riley’s time as a Cleveland judge. Riley remained in the role through Joe Biden’s administration.

The immigration review office said in an August 2021 email to Neil Fleischer, then president of AILA’s Ohio chapter, that the complaint was “reviewed fully and handled appropriately,” and that “this matter is now considered closed,” according to text of the email shared by an Ohio AILA member.

Some Ohio immigration attorneys noticed improvement in Riley’s tone with migrants following her additional training. But at least four lawyers and two additional people familiar with her time in Cleveland said Riley’s targeted questions doubting details in migrants’ stories persisted throughout her time as a judge, leading attorneys to question her impartiality. Riley continues to hear cases at the Cleveland court while serving as chief judge.

Most of the people who spoke to Bloomberg Law about Riley requested anonymity because they continue to represent immigrants at the Cleveland court or because they weren’t authorized to speak publicly.

Riley’s demeanor and behavior have been a repeated concern for attorneys and court staff, two of the people said. Some immigration lawyers refuse to take on cases that go before Riley because of her reputation, according to one Ohio attorney.

In a 2022 hearing, Riley extensively questioned one of DeVito’s African clients when he described a family friend as an “uncle.”

“When she couldn’t herself discern that this person is not a blood relative, she used it as grounds to say that the client was not credible, when in fact, it just represented her lack of cross-cultural understanding of different customs and cultures,” DeVito said.

Margolin said in his statement that the allegations from AILA and other Ohio attorneys “are patently false, and part of a pattern of anonymously mischaracterizing events to defame EOIR leadership as they continue to effectively implement the administration’s plan to enforce the immigration laws of the United States.”

An EOIR spokesperson said in an email that the office seriously investigates any credible complaints submitted against immigration judges and takes corrective action as needed, but that it doesn’t tolerate unsupported claims levied against judges. The spokesperson declined to comment on any specific allegations against Riley.

Riley’s Background

Riley, who is still primarily based in Cleveland, is among judges at a court that attorneys said is known for siding with the government most of the time.

“There’s still good judges there who want to do the right thing, but there is a culture of judges becoming prosecutors and referees aligning with the other team,” said Julie Nemecek, an immigration attorney based in Columbus.

Another immigration attorney who spoke anonymously said Riley gave the impression with intense questioning of migrants that she was acting like a federal prosecutor, including by raising problems she found with migrants’ claims that government attorneys hadn’t raised.

Judges’ backgrounds and court culture can influence how they approach the job, said Emmett Soper, a former immigration judge and counsel to the EOIR director in the Biden administration.

Riley, who graduated from the University of Akron School of Law in 2002, clerked for a Northern District of Ohio judge and worked briefly as a local prosecutor in Cuyahoga County before joining the US attorney’s office in 2009.

‘Rule of Law’ Commitment

As a federal prosecutor, Riley had the reputation of being a strong litigator with a diligent work ethic, said David Sierleja, a former criminal chief in the office who hired her in 2009.

Riley spent late hours in the office and had no problem telling law enforcement agents if she didn’t think there was enough evidence to bring a case, according to another former federal prosecutor who requested anonymity to speak openly about working with Riley.

Riley’s background differs from several of her predecessors who held long careers at the immigration courts or in the administration counseling on immigration law before taking on the role, Soper said.

Former Chief Judge Sheila McNulty, who was fired by the Trump administration in 2025, spent 15 years at EOIR in various roles, including as assistant chief judge and regional deputy judge. MaryBeth Keller held several leadership roles at EOIR since 1988 before her chief judge appointment in 2016, according to online bios.

As an immigration judge, Riley denied asylum in 81% of cases from 2019 to 2025 in Cleveland, where judges had an average denial rate of roughly 75%, according to government data compiled by the Transactional Records Access Clearinghouse.

That’s substantially higher than the national average denial rate for the same period, which was approximately 59%.

As chief judge, Riley isn’t the ultimate decision-maker shaping the courts. She serves under the direction of top DOJ officials, including Attorney General Pam Bondi, who are making decisions that advance the administration’s deportation agenda, former judges and immigration policy analysts said.

That includes the unusual mass firings of more than 100 immigration judges since the start of Trump’s second term, according to estimates from Justice Connection, an organization supporting former and current DOJ employees. Many of those fired were known for having high asylum grant rates or a previous career defending migrants in court.

In O’Brien’s view, the immigration courts needed to change after past administrations gave judges “too much free rein” over migrants’ cases.

“The Trump administration has made a clear effort to ensure that the immigration courts perform their intended functions in accordance with the laws they are charged with applying,” O’Brien said.

Riley’s directives thus far show a “clear commitment” to “ensuring that the immigration court hews closely to the rule of law,” O’Brien said.

For Soper, the former counsel to the EOIR director, Riley’s guidance suggests that the Trump administration sees her as useful to advancing its goals of limiting asylum hearings and increasing deportations.

“She would not have been appointed to this position were she not, broadly speaking, supportive of what this administration is doing when it comes to the immigration courts and immigration law,” Soper said.