This short essay was solicited for the 20th Anniversary Critical Race Theory Workshop in 2009. It celebrates Angela Harris’s trail blazing essay, Race and Essentialism in Feminist Legal Theory. Harris argues against essentialism, which is the idea that we can identify characteristics of identity groups that describe their fundamental experiences and interests. This essay analyzes an important moment in the 2008 Presidential campaign. Just before the New Hampshire Democratic primary, which was predicted to effectively knock Senator Hillary Clinton out of the field, famous feminist Gloria Steinem published an editorial entitled Women Are Never Frontrunners. The editorial contends that a woman could never succeed on front-running Senator Barack Obama’s credentials and that Clinton was being harmed by sexism. This essay argues that Steinem’s editorial exhibits essentialism. Applying masculinities studies theory to the campaign shows that masculinity played a more complicated role for Obama than simply being an advantaging factor. Rather, because of his particular masculine identities, Obama had to simultaneously avoid the stereotype of the angry black man and face criticism for being too feminine.