Malcolm Gladwell, a bestselling author and speaker, faced significant criticism following his performance in a Munk Debate on Media in Toronto in the fall of 2022. The debate featured Gladwell and New York Times columnist Michelle Goldberg defending mainstream media against journalist Matt Taibbi and author Douglas Murray, who argued that the media could not be trusted.

Before the debate began, audience members voted on the motion, “Be it resolved, don’t trust mainstream media.” Fifty-two percent supported Gladwell and Goldberg's position. However, as the debate unfolded, Gladwell's performance was perceived as lacking. He appeared unprepared and engaged in personal attacks, labeling Taibbi and Murray as conspiracy theorists.

Taibbi highlighted the decline in trust in journalism by referencing polls that once named American journalist Walter Cronkite as “the most trusted man in America.” In response, Gladwell mischaracterized Taibbi's argument, suggesting he longed for a time when a “white man in a suit” dominated the news narrative. This comment drew criticism from Taibbi, who felt it implied he was racist.

The debate concluded with a significant shift in audience opinion. After hearing arguments from both sides, the audience's votes swung by 19 percent, marking the largest voter shift in Munk Debate history. Ultimately, 67 percent of attendees left believing that mainstream media could no longer be trusted.

In a subsequent episode of his podcast, Revisionist History, Gladwell acknowledged his shortcomings during the debate. He admitted, "We lost because we weren’t listening. I wasn’t listening. I was so caught up in my own head, in my own argument, that I didn’t hear what the other side was saying, and I didn’t hear what the audience was saying.”

Later in March 2023, Gladwell led a discussion on the inclusion of transgender athletes in sports at the MIT Sloan Sports Analytics Conference in Boston. He introduced the topic with what he termed a “dumb martian question,” asking whether the historical separation of men and women in sports still made sense. He referenced the past exclusion of women from events like the Olympics, suggesting that the rationale for separate categories might need reevaluation.

However, critics noted that framing the question this way implied that the previous exclusion of women was flawed, which could mislead the discussion about current policies regarding transgender athletes. During the panel, there was little disagreement among the members. Sports scientist Ross Tucker emphasized that no amount of testosterone could elevate women to the level of elite male athletes.