Book Review: The Gray Lady Winked by Ashley Rindsberg
Ashley Rindsberg’s The Gray Lady Winked is, in many ways, a direct critique — some might say a hit piece — on The New York Times. The book systematically examines the paper’s history of misreporting, arguing that it has often served ideological and institutional interests rather than objective journalism. While Rindsberg presents a compelling case, his perspective leans toward the new right and is noticeably sympathetic to new media as an alternative to legacy institutions.
The book details how The New York Times has repeatedly gotten major stories wrong over the decades. Some of the most egregious examples include:
• Nazi Germany: The Times relied on a foreign correspondent who was, at best, a Nazi sympathizer, failing to provide accurate reporting on the rise of National Socialism. The paper’s favorable coverage of the 1936 Berlin Olympics also played into Nazi efforts to propagandize the world on the superiority of the Aryan race.
• The Soviet Union: The Times was notoriously sympathetic in its coverage of the USSR, downplaying atrocities like pogroms and whitewashing policies that led to famine and suffering, dismissing them as “growing pains.”
• Vietnam War: Its reporting on Vietnam failed to paint a full picture, neglecting the atrocities committed by both sides and not offering enough critical analysis of U.S. involvement. This likely played a role in misinforming the public as to what their country was really doing in Vietnam in the first place. Had the public really known what was going on perhaps the anti war movement would have had more success sooner.
• Iraq War: The Times played a role in perpetuating the false narrative of weapons of mass destruction in Iraq, which helped manufacture public consent for war — something that aligns with Noam Chomsky’s theory of media propaganda.
Rindsberg also critiques how, in recent years, The New York Times has become less ideologically tolerant of dissent within its own ranks. He highlights the departure of figures like Bari Weiss, who left the paper amid accusations that it enforces a rigid ideological worldview among its journalists.
The overarching takeaway is that The New York Times — despite its reputation as “the paper of record” — is ultimately just an institution made up of people with biases, blind spots, and intellectual shortcomings. Interestingly, the paper has been privately controlled by the same family for five generations, making it something of a media dynasty rather than a neutral beacon of truth.
The book challenges The New York Times’ place in pop culture as an unimpeachable journalistic authority. If journalism is meant to speak truth to power, then when an institution reaches the level of influence the Times has, it arguably becomes a mechanism of power itself.
While the future of journalism may not lie with legacy outlets like The New York Times, The Gray Lady Winked serves as a reminder that no source should be taken at face value — everything in our media diet deserves skepticism.
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