Trump Administration Faces Legal Challenges from Judges Appointed by Obama and Biden
President Donald Trump’s second term has been marked by a flurry of executive orders, exceeding 80 since January, which have triggered a wave of legal challenges, with over 100 lawsuits filed against his administration. This has led to a heated debate regarding the balance of power between the executive and judicial branches. Democratic lawmakers have voiced concerns about a potential constitutional crisis stemming from the administration’s actions, while the White House has criticized what it perceives as judicial overreach by lower court judges.
White House press secretary Karoline Leavitt has expressed strong disapproval of injunctions issued by district court judges that impede the president’s ability to implement his agenda. She characterized such actions as an "absurd" attempt to usurp the executive authority of the President. Leavitt accused certain judges of being "judicial activists" seeking to obstruct President Trump’s executive powers.
The article highlights several judges appointed during the Obama and Biden administrations who have issued rulings against the Trump administration’s policies.
Judge James E. Boasberg (Obama Appointee)
Judge Boasberg, currently serving as the chief judge of the United States District Court for the District of Columbia, was initially appointed to the District Court in 2011 by President Obama. He has a history of ruling against the Trump administration, including blocking Arkansas, Kentucky, and New Hampshire from implementing work requirement waivers for Medicaid recipients. The Trump administration’s Department of Health and Human Services had introduced a policy allowing states to enforce these waivers.
The U.S. Court of Appeals for the D.C. Circuit upheld Boasberg’s decision in the Kentucky and Arkansas case, stating that former Health and Human Services Secretary Alex Azar had not adequately analyzed whether the demonstrations would promote the primary objective of Medicaid – to furnish medical assistance. The Supreme Court later dismissed all pending cases related to the Medicaid work requirements in April 2022.
Boasberg also issued an order halting the Trump administration from deporting migrants under the Alien Enemies Act of 1798. However, the deportation flight continued to El Salvador, and Leavitt argued that Boasberg’s order had "no lawful basis" as it was issued after the flight had departed U.S. airspace.
Boasberg’s background includes a degree from Yale College and Yale Law School. He also served on the United States Foreign Intelligence Surveillance Court from 2014 to 2021.
Judge Leo T. Sorokin (Obama Appointee)
Judge Sorokin, appointed to the United States District Court for the District of Massachusetts by President Obama in 2014, previously served as a magistrate judge on the same court. He is known for spearheading the RISE program in Massachusetts, a delayed-sentencing program that offers eligible criminal offenders a yearlong delay in sentencing to undergo an intensive supervision program. Sorokin has expressed his satisfaction with the restorative justice aspect of the RISE program and its expansion.
Sorokin blocked the Trump administration from implementing an executive order to ban birthright citizenship, joining other judges from Maryland and Washington state in issuing nationwide injunctions against the ban. The Trump administration requested the Supreme Court to intervene and allow the order to be executed.
Sorokin is an alumnus of Columbia Law School and has served as a professor at Boston University School of Law.
Judge Amir Ali (Biden Appointee)
Judge Ali is a recent appointee to the United States District Court for the District of Columbia, joining the court in December 2024. He played a key role in launching the MacArthur Justice Center’s Washington, D.C., branch in 2017, a nonprofit law firm specializing in criminal justice reform and civil rights issues. Ali argued and won two cases before the Supreme Court on behalf of the MacArthur Justice Center.
During his confirmation hearing, Ali faced scrutiny regarding remarks made by a colleague at the MacArthur Justice Center about defunding the police. However, Ali clarified that he did not share those views, nor did the MacArthur Justice Center.
In March, Ali ruled that the Trump administration likely exceeded its constitutional authority when it sought to halt payments to contractors by the State Department and USAID, totaling $2 billion in funding approved by Congress.
Ali has taught classes on civil, criminal, and appellate litigation at institutions such as Harvard Law School and Georgetown University Law Center.
Judge Beryl A. Howell (Obama Appointee)
Judge Howell joined the United States District Court for the District of Columbia in 2010 after serving as staff and general counsel of the United States Senate Committee on the Judiciary.
Howell ruled against the Trump administration, stating that the president did not have the authority to fire members of the National Labor Relations Board at will. This ruling followed the Trump administration’s dismissal of National Labor Relations Board chair Gwynne Wilcox, who subsequently filed a lawsuit alleging a violation of the National Labor Relations Act. Howell ordered Wilcox to be reinstated to her position.
Howell made note of Trump’s self-portrayal as a "king" or "dictator," suggesting such an image misunderstands the role under Article II of the U.S. Constitution.
Howell attended Columbia University School of Law and served as the deputy chief of the narcotics section and an assistant U.S. attorney in the U.S. Attorney’s office for the Eastern District of New York.
Judge Ana C. Reyes (Biden Appointee)
Judge Reyes joined the United States District Court for the District of Columbia in February 2023, following a career as a litigation attorney focusing on international litigation. She has also represented refugees for groups like the United Nations High Commissioner for Refugees and Human Rights First.
Reyes is currently overseeing a case filed by LGBTQ legal rights advocacy groups against the Trump administration’s executive order barring transgender individuals from serving in the military. The groups are seeking a preliminary injunction pausing the ban during litigation, and Reyes is expected to issue a decision on the injunction.
Reyes attended Harvard Law School and has co-taught classes at Yale Law School and Georgetown University Law Center on trial practice and advocacy in international arbitration.
Judge Zia M. Faruqui AliKhan (Biden Appointee)
Judge AliKhan joined the United States District Court for the District of Columbia in December 2023, after serving as an associate judge for the D.C. Court of Appeals.
AliKhan ruled against the Trump administration, indefinitely blocking the administration from freezing federal grants and loans. This ruling stemmed from a lawsuit filed by nonprofit organizations following the Trump administration’s Office of Management announcement of a pause in loans and grants. Although the administration rescinded the memo, the White House clarified that the order remained in effect.
AliKhan characterized the freeze as "ill-conceived from the beginning," stating that the administration’s actions were "irrational, imprudent and precipitated a nationwide crisis."
AliKhan attended Georgetown University Law Center and supported O’Melveny & Myers, LLP’s Supreme Court and Appellate Practice Clinic at Harvard Law School, as well as the legal writing program at Yale Law School.
The numerous lawsuits and legal challenges against the Trump administration highlight the tensions between the executive and judicial branches. The administration’s criticism of "low-level" judges and accusations of judicial activism underscore the contentious nature of these legal battles. The outcomes of these cases could have significant implications for the scope of executive power and the role of the judiciary in checking presidential actions.
