In March 2017 he wrote a letter to Evergreen faculty, objecting to a change in the college's decades-old tradition of observing a "Day of Absence" during which minority students and faculty would voluntarily stay away from campus to highlight their contributions to the college. The announced change would flip the traditional event, asking white participants to attend an off-campus program to talk about race issues while the on-campus program was designated for participating people of color. Weinstein said this established a dangerous precedent. In response, the organizers stated that participation was voluntary and that no one implied that all white people should leave. In May 2017, student protests disrupted the campus and called for a number of changes to the college. The protests involved allegations of racism and intolerance and threats, and brought national attention to Evergreen, sparking further debate about free speech on college campuses. During the protests, there was an altercation between protesters and Weinstein. In a lawsuit brought against the school by Weinstein and his wife Heather Heying, Weinstein said the college's president did not ask campus police to quell student protesters. Weinstein also said campus police told him that they could not protect him and encouraged him to stay off campus. Weinstein then held his biology class in a public park. In September 2017, a settlement was reached. Weinstein and Heying resigned and received $250,000 each, after having sought $3.8 million in damages.
Post-Evergreen
Following his resignation from Evergreen, he appeared on Sam Harris's podcast, Joe Rogan's podcast multiple times, and he moderated two debates between Jordan Peterson and Sam Harris. He appears in the documentary No Safe Spaces, which documents the Evergreen incidents. Weinstein's brother, Eric Weinstein, coined the term "the Intellectual Dark Web", and described Weinstein as a member. The term refers to a group of academics and media personalities who publish outside of the mainstream media. In June 2019, Weinstein began the DarkHorse Podcast. He was a 2019-2020 James Madison Program Visiting Fellow at Princeton University.
Weinstein is Jewish. He is married to Heather Heying, an evolutionary biologist who also worked at Evergreen. Heying resigned from the college with Weinstein, having taken a similar position during the Day of Absence controversy. Weinstein describes himself as a political progressive and left-libertarian. He appeared before the U.S. House Oversight Committee on May 22, 2018, to discuss free speech on college campuses.