Several of the federal judges hearing lawsuits threatening key tenets of President Donald Trump’s agenda have a legal history with the president.
The Trump administration has been fraught with legal challenges regarding issues ranging from banning transgender people from serving in the military to deporting violent criminal gang members in the country illegally. Some of the judges handling those cases have been handing down rulings about Trump for years.
For instance, New York-based U.S. District Judge Paul Engelmayer, who blocked the Department of Government Efficiency from accessing Treasury Department records last month, overturned a federal rule in 2019 during Trump’s first term that would have granted healthcare workers greater leeway in opting out of providing procedures, such as abortions, for religious reasons.
Here is a look into a few other judges hearing critical cases who have a history with Trump going back years, in some cases.
Tanya Chutkan
U.S. District Judge Tanya Chutkan has a mixed history with the Trump administration. On Tuesday, the District of Columbia-based judge ruled against the Environmental Protection Agency’s recent effort to terminate billions worth of climate grants to green groups. However, the Obama appointee also declined to allow the groups access to the funds.
On the other hand, Chutkan handed Trump’s Department of Government Efficiency a small victory last month after she denied a wide-ranging request from a group of Democratic attorneys general seeking to limit DOGE’s power.
Chutkan had a history of being less than sympathetic to the president during her oversight of his 2020 election federal criminal case, and she bashed him last month after he issued pardons for many Jan. 6, 2021, Capitol riot defendants.
Ana Reyes
U.S. District Judge Ana Reyes on Tuesday blocked the Trump administration from carrying out an executive order that prevents transgender people from serving in the military. The Biden appointee wrote that the ban constituted “cruel irony” that “thousands of transgender service members have sacrificed—some risking their lives—to ensure for others the very equal protection rights the Military Ban seeks to deny them.”
Another court ruling Reyes handed down last month was more favorable to the Trump administration. On Feb. 14, Reyes denied the requests of eight inspectors general fired by Trump who asked to be immediately reinstated.
Theodore Chuang
On Tuesday, Obama-appointed U.S. District Judge Theodore Chuang issued a scathing rebuke of the Trump administration’s effort to dismantle the U.S. Agency for International Development.
“The Constitution’s Appointments Clause and separation of powers stand as a bulwark against precisely this kind of unilateral executive action,” Chuang wrote.
The judge previously ruled against Trump during his first term in office, blocking parts of the president’s proposed travel ban affecting Syria, Libya, Iran, Yemen, Chad, Somalia, North Korea, and Venezuela. Chuang also ruled in 2020 that Trump’s Food and Drug Administration could not require women to visit a doctor in person to obtain a medical abortion.
James Boasberg
On Saturday, U.S. District Judge James Boasberg, another Obama appointee, issued a nationwide injunction blocking Trump’s plan to deport suspected members of Tren de Aragua, a Venezuelan gang — a ruling for which the president called for him to be impeached.
The judge has since pressed the Trump administration after members of the gang were transported overseas even as he issued a ruling to block the deportations.
Boasberg’s prior cases with Trump include an order he issued in 2023 directing former Vice President Mike Pence to testify in front of a grand jury about his contact with the president in the days leading up to Jan. 6, 2021. The judge also handed down a ruling Monday barring seven law enforcement officers who had sued Trump over Jan. 6 from accessing grand jury information in his prior criminal case.
Beryl Howell
U.S. District Judge Beryl Howell, also an Obama appointee, earlier this month ordered a member of the National Labor Relations Board to be reinstated after Trump fired her. The judge additionally ruled against Trump after he issued an order stripping Perkins Coie, a Democratic-linked law firm, of its staff’s security clearances and demanding an end to any federal contracts it has with the government.
JUDGES BLOCKING TRUMP GOVERNMENT EFFICIENCY MOVES HAVE HISTORY OF ACTIVISM
She was also involved in court cases from Trump’s first term alleging that the president had colluded with Russia to win the 2016 election, claims which were later disproven.
In 2017, Howell authorized the FBI to search at least two Twitter accounts belonging to Trump associate Roger Stone for information related to the Russia-Trump case. Other rulings affecting the case included her 2019 decision ordering that House Democrats be given access to grand jury material and testimony from former special counsel Robert Mueller’s Russia collusion investigation.