‘Reporter’ Who Doesn’t Know Who Signs Her Paychecks Declares Victory Over ‘Legacy Media’

As someone who’s worked in New York media for over a decade now, there are a lot of really fucking annoying/terrible/rip-your-hair-out insufferable media people. The worst offenders tend to be both self-mythologizing and deeply shit at their jobs. So, in 2026, no one is more deserving of “Worst Person in Media” than The Free Press “reporter,” Olivia Reingold. 

This week, Bari Weiss’ venture-capital-backed and genocide-supporting website got itself a sparkling Times Square billboard—because, again, it’s backed by venture capitalists and was scooped up by a giant news network in October. Reingold rushed to memorialize the moment with another cringe video—and a seemingly deep misunderstanding of who she works for.

After filming herself standing in front of the ad, Reingold then runs up to the camera to say directly into the lens, “Read it and weep, legacy media!” Bestie, you were purchased by CBS News, aka Legacy Media, aka owned by Paramount, in October, for a rumored $150 million. That billboard is a product of legacy media, not proof of triumph over it. As you can see in the video, it is literally hanging above a Paramount sign. Sigh. I loved her shirt, though. 

If you vaguely recognize her name but still can’t quite place her, she’s the ~reporter~ who said certain starving children in Gaza—who were suffering under Israel’s genocide—were only starving because they had pre-existing medical conditions. Just a breathtaking level of moral and journalistic failure. John Oliver also did a brutal takedown of Bari Weiss and The Free Press in October, after the CBS acquisition—and Reingold responded with one of the most cringe-inducing, painfully unfunny attempts at satire I’ve ever seen. I can’t even bring myself to rewatch it, but here’s the link.

Last week, Reingold displayed her lack of reporting chops yet again while attempting—and failing—to create a gotcha moment with U.S. Senate candidate Abdul El-Sayed at a rally in Michigan. Or, as Defector’s Tom Levy put it in his headline: “Free Press Dipshit Humiliates Herself in Public Again.”

Actually, calling her a “person in media” feels generous—both to her and deeply insulting to everyone else.

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