This paper argues for the continuing significance of D. W. Winnicott’s work. A main goal of the paper is to show that Winnicott is especially needed to respond to threats to higher education, especially in the United States context. American politics have been highly charged for several election cycles, and American higher education has come under increased scrutiny if not direct attack. This paper argues that the American public has lost faith in higher education, and that one way to rebuild faith is to engage with Winnicott’s thinking. I am especially interested in the ways that Winnicott helps us push back against influencer culture, making space for the good enough, and appreciating how higher education isn’t just one influence among others. Rather, higher education, when it is working, facilitates student freedom.