A growing body of medical research has focused on the chemical compound psilocybin in recent years. However, this research is not merely a scientific issue but also a social and political one. In the 1960s, psilocybin and other psychedelics were often ingested outside of research settings. This alarmed many people, resulting in severe legal restrictions on psilocybin research. Today, many psilocybin advocates hope that it will avoid the negative public sentiment of the 1960s. To help gauge public sentiment about other psychoactive compounds, some studies have examined newspaper coverage. The present study hoped to build a similar gauge with newspaper coverage of psilocybin. The author hypothesized that general sentiment about psilocybin has become more positive among American newspapers in recent years and that the annual number of newspaper articles mentioning psilocybin has increased. To test these hypotheses, all mentions of psilocybin were examined in four regional American newspapers from January 1, 1989, to December 31, 2020. Contrary to the hypotheses, a significant rise in positive sentiment was seen in only one of these newspapers, and the annual number of articles mentioning psilocybin significantly increased in only one newspaper. These results could be a warning to psilocybin advocates about the risk of negative social and political sentiment growing again.