Norm Eisen, a former Obama White House lawyer and U.S. ambassador to the Czech Republic, has in recent months emerged as one of the Trump administration’s most prominent legal antagonists.

Through a nonprofit group he founded, Democracy Defenders Fund, Eisen has helped to wage a series of key court battles challenging the administration over issues like birthright citizenship, the Federal Reserve and the Kennedy Center, claiming some victories in a fight against what he calls President Donald Trump’s executive overreach.

But Eisen’s recent work with two vocal critics of Israel who have faced accusations of antisemitism has raised some eyebrows in the Jewish community, owing to his identification as a liberal Zionist whose record includes combating anti-Jewish prejudice at home and abroad.

In a broader effort to take on those he views as the president’s “enablers” outside of government, Eisen has notably teamed up with actor Mark Ruffalo, one of the fiercest detractors of Israel in Hollywood, to block the merger of Paramount and Warner Bros. Discovery — a pending deal opponents warn would consolidate ownership in the hands of a Trump ally.

Last month, Ruffalo drew backlash from Jewish leaders who said he had used antisemitic rhetoric in social media posts attacking David Ellison, the CEO of Paramount, and his father, Larry, the founder of Oracle and a top Trump donor whom the actor said “will own most of ‘Para Bros.’” Ruffalo accused the Ellisons of enabling “genocide,” claiming Oracle had been “built on an apartheid system of oppression” in Gaza, among other statements linking the deal to the Middle East.

Amid the subsequent fallout, Eisen, for his part, reportedly tried to enlist Jonathan Greenblatt, the CEO of the Anti-Defamation League, to help Ruffalo convey contrition for his social media comments, but was rebuffed. A spokesperson for the ADL declined to comment on Eisen’s alleged outreach to Greenblatt — who called Ruffalo’s remarks “cynical and sickening.”

Eisen then reportedly worked to gather support from more than 180 Jewish entertainment figures who signed an open letter defending Ruffalo amid what they criticized as a “smear campaign” promoting “spurious charges of antisemitism” against the actor.

Eisen denied the alleged back-channeling on Ruffalo’s behalf. “I did not work on the letter and I was not rebuffed by ADL,” he said in a statement to Jewish Insider shared by a press representative on Wednesday. 

Meanwhile, Eisen has touted his role in helping to represent Karen Attiah, who was recently reinstated as a columnist at The Washington Post after a private arbitrator concluded the paper wrongly fired her over social media comments she made about the killing of Charlie Kirk.

While her termination was not related to remarks about Israel, Attiah has faced scrutiny in the Jewish community for her writings and social media activity in the wake of Hamas’ Oct. 7, 2023, attacks, including the promotion of messages that justified the violence.

Eisen hailed the arbitrator’s decision as “a landmark victory for one of our nation’s crusading journalists” and shot a celebratory video with Attiah afterward — even as some free speech advocates questioned if the case could be reasonably argued on First Amendment grounds since it was not tied to the government but a paper owned by Jeff Bezos, who has cultivated ties to the Trump administration.

The American legal tradition has long rested on the principle that attorneys need not share their clients’ views in order to represent them. Still, Eisen’s work with Ruffalo and Attiah has provoked quiet curiosity among Jewish leaders familiar with his involvement in pro-Israel and Jewish causes.

Eisen, an Orthodox Jew, served as assistant director of the ADL’s Los Angeles office before he became the chief White House ethics lawyer to former President Barack Obama, a Harvard Law School classmate, earning the nickname “Mr. No” for his Talmudic commitment to upholding rules and standards. 

He was later appointed ambassador to the Czech Republic, a particularly significant post for Eisen, whose mother was deported to Auschwitz from what was then Czechoslovakia during World War II.

In 2018, Eisen, who is now a senior fellow at the Brookings Institution, published a book, The Last Palace: Europe’s Turbulent Century in Five Lives and One Legendary House, centering on the villa in Prague where he had lived as ambassador, which was built by a Jewish financier after World War I and was later occupied by the Nazis.

In a statement to JI on Monday, Eisen said that he was “proud to represent Karen Attiah in her unjust firing by The Washington Post — a firing that has been adjudicated illegal,” while noting that he was also “proud to work side-by-side with Mark Ruffalo to block the Paramount Warner’s merger.”

“Do I agree with them — or with anyone — on every issue? Of course not. I am a Zionist who supports a two-state solution (and is strongly anti-Bibi),” Eisen added, using the nickname for Israeli Prime Minister Benjamin Netanyahu.

“But,” he argued, “I believe it is OK and indeed mandatory to agree to disagree on particular issues while we join together on the cause of defending US democracy from an authoritarian president like Donald Trump — and his autocratic enablers like Bezos or the Ellisons.”