A judge who blocked President Donald Trump’s attempt to expedite deportations of gang members once participated in a mock trial with former Vice-President Kamala Harris’ husband — and he is not the only judge stonewalling Trump’s orders that has a conflict of interest.
Chief Judge of the D.C. District Court James Boasberg temporarily blocked the Trump administration from using the Alien Enemies Act, a 18th-century wartime law, to arrest and deport alleged members of the Venezuelan gang Tren de Aragua.
Now the president is accusing Boasberg of having a “conflict of interest” because of his past relationship with Harris’s husband, entertainment lawyer Doug Emhoff.
In 2022, Boasberg participated in a mock trial with Emhoff. Trump posted a photo of Emhoff with Boasberg at the Shakespeare Theater Company’s (STC) 2022 Mock Trial on Truth Social.
“SUCH A CONFLICT OF INTEREST!” Trump wrote.
The mock trial was moderated by Abbe David Lowell, who previously served as Bill Clinton’s lawyer during the Monica Lewinsky scandal. He was also Hunter Biden’s attorney amid legal battles related to a failure to pay his taxes and illegal possession of a firearm. In 1998, The Washington Post deemed Lowell the “Defender of Democrats in Trouble.”
Boasberg was recently assigned to a lawsuit filed against some of the officials in the leaked Signal chat, including Defense Secretary Pete Hegseth, Director of National Intelligence (DNI) Tulsi Gabbard, and Central Intelligence Agency (CIA) Director John Ratcliffe.
The editor-in-chief of The Atlantic was inadvertently added to a group chat about Houthi strikes on the messaging app Signal by National Security Adviser Mike Waltz, according to a piece published Monday. (RELATED: Gregg Jarrett Says Defiant Lower Court Judges Better Learn That ‘An Alien Can Be Removed Without A Hearing’)
Boasberg was appointed by former President Obama, and he has an extensive history of ruling against the Trump administration.
Boasberg was the sentencing judge for FBI lawyer Kevin Clinesmith, who altered an email about former Trump campaign aide Carter Page in order to support a Foreign Intelligence Surveillance Act (FISA) application to spy on Page during the 2016 presidential campaign. Clinesmith was one of the key players in the FBI’s Operation Crossfire Hurricane, which investigated potential ties between the Trump campaign and the Russian government.
Prosecutors sought between three and six months in prison for Clinesmith, but Boasberg sentenced him to mere probation.
Boasberg also approved the FBI’s use of a warrantless surveillance tool, Section 702 of the FISA Amendments Act, when he presided over the Foreign Intelligence Surveillance Court (FISC) in 2021.
This decision came after the court discovered the bureau had violated privacy rules regarding Section 702, according to The Washington Post. (RELATED: Jonathan Turley Says Trump Is ‘Likely To Win’ Cases Against Judges Attempting To Block Deportations)
John Roberts personally placed James Boasberg on the FISA court that rubber-stamped illegal spy warrants against Donald Trump.
In case you’re wondering why he’s setting his own credibility on fire to defend Boasberg from impeachment investigations.
— Sean Davis (@seanmdav) March 18, 2025
Boasberg also ruled against Trump’s immigration policies during the first administration. In one instance in 2018, he sided with the American Civil Liberties Union (ACLU) and ruled against Trump’s efforts to detain migrants claiming asylum.
He was also involved in the eventual public disclosure of Hillary Clinton’s emails. Just before the 2016 election, Boasberg ruled that most of Hillary Clinton’s emails would not become public until after Election Day, The Wall Street Journal reported.
He ordered the State Department to complete the processing of 1,050 pages out of potentially 10,000 pages of evidence by November 4, according to the outlet.
Trump blasted Judge Boasberg on Truth Social Thursday and called for an investigation.
“There is no way for a Republican, especially a TRUMP REPUBLICAN, to win before him,” Trump said.
“He is Highly Conflicted, not only in his hatred of me — Massive Trump Derangement Syndrome! — but also, because of disqualifying family conflicts.”
Boasberg’s wife, Elizabeth “Liddy” Manson, has ties to Democratic causes. She donated to Democrats, including Elissa Slotkin for Congress in 2021, and the left-wing donation site ActBlue, FEC filings show.
She also founded an abortion clinic in Virginia called Meadow Reproductive Health and Wellness, according to her LinkedIn.
While much of the attention has centered around Boasberg, he is not the only judge with a potential conflict of interest.
WASHINGTON, DC- March 16:
Judge James E. Boasberg, chief judge of the Federal District Court in DC, stands for a portrait at E. Barrett Prettyman Federal Courthouse in Washington, DC on March 16, 2023. (Photo by Carolyn Van Houten/The Washington Post via Getty Images)
Judge Amy Berman Jackson was also at the mock trial with Doug Emhoff, and she donated to Democratic candidates.
Jackson donated $1000 to Bill Clinton in 1992 and $500 to Alex Sanders in 2002, according to Open Secrets. Both of the donations occurred before she was a U.S. district judge.
Jackson sentenced former Trump advisor Roger Stone to more than 3 years in prison in 2020 after he was charged with obstructing a congressional investigation and witness tampering.
She harshly criticized Trump and claimed he “propagat[ed] the lie that inspired [January 6],” CNN reported.
Jackson also temporarily reinstalled the head of the Office of the Special Counsel (OSC), Biden appointee Hampton Dellinger, after he was fired by Trump this year, according to The Hill.