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Jon Lovett of Crooked Media on Lovett or Leave It Live Tour, April 2024, Washington, D.C.
The Crooked Media cofounder who will be in Washington, D.C., for a taping of his Lovett or Leave It podcast, told The Advocate that Democrats must stand firm.
As institutions face intensifying pressure under Donald Trump’s second presidency, Jon Lovett is urging them not to cave.
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“I think it’s fucking terrible,” Lovett told The Advocate Tuesday in an interview about the Trump administration’s renewed attacks on LGBTQ+ Americans, immigrants, and core democratic principles. The Crooked Media cofounder and former Obama speechwriter is in Washington, D.C., as part of White House Correspondents’ Dinner week for a live taping of his podcast Lovett or Leave It at the Lincoln Theatre on Thursday, but his focus remains squarely on the stories not making it to the gala stages — like the fate of a gay asylum-seeker deported without due process or the government’s insistence that transgender Americans are unfit to serve in the military.
Related: Gay asylum-seeker’s lawyer worries for the makeup artist's safety in Salvadoran ‘hellhole’ prison
Lovett’s warning came as some major universities were resisting administration demands. Harvard has refused to comply with Trump’s sweeping oversight demands, while others, like Columbia, have capitulated, surrendering academic freedom, policing their own campuses, and still failing to reclaim threatened federal funding.
“We see Columbia capitulate, and the demands keep coming,” Lovett said. “We see law firms capitulate. … We see Paramount enter talks with Trump over this frivolous lawsuit about 60 Minutes. When a news organization caves, they’re more afraid of Trump than of their journalists and producers. And that has to change.”
Lovett called the political moment “a very big fight that will last years” and warned that institutional surrender invites only more authoritarian overreach. “Every inch Trump gets is an inch we don’t get back,” he said.
Nowhere is that erosion more evident than in the case of Andry José Hernández Romero, a 31-year-old gay Venezuelan asylum-seeker who entered the U.S. legally through the CBP One app. After being detained in California, passing a credible fear interview, and awaiting his asylum hearing, he was suddenly deported to El Salvador in March under the Alien Enemies Act.
Related: Democratic lawmakers fly to El Salvador & demand U.S. Embassy action on gay man Trump sent to CECOT prison
“This gay makeup artist is in a nightmare,” Lovett said. “And there is something about the gayness of this person, the femininity of the photos he’s posted on social media, that I do think makes people feel connected and more emotional about it in a way that is really sad and moving.”
Hernández Romero’s deportation was triggered by a disgraced former police officer working for CoreCivic, a private prison contractor. The officer cited two crown tattoos — tributes to Hernández Romero’s parents and the Three Kings Day pageants he performed in, according to his attorney — as alleged gang symbols. U.S. officials used those tattoos and social media posts featuring beauty tutorials to justify his deportation. He was later identified in video footage posted by the Salvadoran government, shackled and sobbing, being marched into the CECOT mega-prison — where thousands are held without trial, daylight, or communication.
“They claim that his social media makes clear he’s a member of this gang,” Lovett said. “And then you look at what he’s posted — glamour shots and makeup shots and beauty shots — and it’s ridiculous.”
Lovett pointed to a Time photojournalist who captured the most chilling moment: Hernández Romero pleading, “I don’t belong here. I’m gay.”
“Obviously, that doesn’t make sense literally,” said Lovett, who is gay. “But then I think for all of us, we understand why it does make sense.”
Democratic lawmakers, including U.S. Rep. Robert Garcia, traveled to El Salvador this week and confirmed to The Advocate that they’ve requested a formal wellness check and proof of life. “He hasn’t had any access to his family or legal counsel or really anyone,” Garcia said.
Lovett praised the push for accountability but noted the broader threat: “If the government can disappear people without due process and then claim they no longer have the ability to rectify it because they’re in a foreign jail — that is a Kafkaesque bureaucratic doom loop.”
“They’ve now been down there for five weeks, five weeks, five weeks — no contact, no understanding of whether or not they’ll ever get out. No sentence. No ability to call a lawyer or call family. That’s a living nightmare. They’re in a living nightmare. And the news cycle can move to tariffs. It can move to [Defense Secretary] Pete Hegseth. But Andry hasn’t moved. He’s there. He’s stuck.”
Lovett also discussed the administration’s revived transgender military ban, currently being challenged in Talbott v. United States, a case argued Tuesday before the U.S. Court of Appeals for the D.C. Circuit. “The order is not written to say gender-affirming care creates burdens,” Lovett said. “It is that being trans makes you inherently unfit to serve in not so many words.”
Related: Trump’s DOJ struggles defending trans military ban during D.C. appeals court hearing
During oral arguments, the Trump administration faced sharp skepticism from the three-judge panel. Judge Cornelia Pillard dismissed the government’s logic, pointing out that the policy explicitly bans transgender people who have transitioned, regardless of medical diagnosis. “Your argument is that you can serve as a transgender person as long as you don’t serve as a transgender person,” she said.
Department of Justice attorney Jason Manion repeatedly admitted that he did not know how the policy would be enforced or how many service members it would impact. In earlier district court proceedings, Judge Ana Reyes blasted the government’s rationale as “soaked in animus and dripping with pretext.”
Lovett said the animus is clear. “It couldn’t have been written more clearly as to show animus towards trans people who have served this country in uniform—something that obviously Donald Trump has never done.”
While recognizing polling setbacks on trans issues, Lovett emphasized, “The American people do not support what this administration is doing. The majority of this country still understands and respects the service of trans people.”
Lovett said there’s only one way forward in the face of a looming dictatorship.
“If we all say no, if we all stand up, we’re stronger, and Trump is weaker. And if Trump is able to pick off institutions and companies and organizations one by one, he gets stronger, and we get weaker. And that, to me, is the main central test over the next couple of years.”
