Because the internet gutted its ad revenue. Back in 2000 the paper's strength was in its advertising: https://www.nytimes.com/2000/04/14/business/times-co-profi

Because the internet gutted its ad revenue. Back in 2000 the paper's strength was in its advertising: https://www.nytimes.com/2000/04/14/business/times-co-profit-is-up-35-on-strength-in-advertising.html https://www.nytimes.com/2000/04/14/business/times-co-profit-... Over the course of the 2000s, the stock price of the NYT would drop to less than one quarter of what it was in 2000, and only start to climb back up in late 2016 and early 2017.