This Article uses the September 2017 defamation decision in Simmons v. American Media, Inc. as a springboard for examining defamatory meaning and reputational injury. Specifically, it focuses on cases in which judges acknowledge that plaintiffs have suffered reputational harm yet rule for defendants because promoting the cultural value of equality weighs against redress. In Simmons, a normative, axiological judgment--that the law should neither sanction nor ratify prejudicial views about transgender individuals-- prevailed at the trial court level over a celebrity's ability to recover for alleged reputational harm. Simmons sits at a dangerous intersection: a crossroads where a noble judicial desire to reject prejudicial stereotypes and to embrace equality collides head-on with an ignoble reality in which a significant minority of the population finds a particular false allegation (in Simmons, transgender status) to be defamatory. This Article examines how courts historically determined defamatory meaning and how once-defamatory per se statements about sexual orientation are not always considered so today. When viewed beyond a legal lens, however, research suggests transgender individuals have not witnessed the same benefits of that altered perspective. There is a key difference between attitudes about sexual orientation and attitudes about sexual identity. The Article concludes by proposing variables for courts to apply in future cases where a dispute exists over whether an allegation is defamatory per se, rather than leaving the decision to the discretion of judges untethered from formal criteria.