This research explores the concept of endorser transgressions and its effects on the endorsed brands. Further exploring the meaning transfer model, which suggests that the positive traits of endorsers are transferred unto the consumer goods which they endorse, we explore whether the opposite principle holds true; do the negative traits associated with a transgressing endorser transfer unto the brands they endorse. We employ Metts’ (1994) definition of a transgression as a violation of the implicit or explicit rules guiding relationship performance and evaluation. Our main focus is to see if the nature of an endorser’s transgression influences the way consumers respond to that endorser, and the endorsed brand, post-transgression. We key in on transgressions within vs. outside an endorser’s essence, where essence is defined as “the significant individual feature of the endorser, which is inseparable from his nature.” For example, the essence of Lebron James is basketball, while the essence of Meryl Streep is acting. We posit that transgressions within endorsers’ essence (vs. outside) will be viewed more negatively by consumers and that brands that stick with the endorser post-transgression will also be negatively viewed. We test the proposed hypotheses with an experimental design and find that differences exist between consumers on their evaluations on attitudes toward the endorser when the transgression is within the core essence of the endorser vs. outside the essence (e.g., athlete cheating with performance-enhancing drugs vs. marriage infidelity). We also find that when the transgression is within the context for which the endorser is employed by a brand, it negatively impacts consumers’ intent to patronize a brand that sticks with the endorser. This is a particularly interesting finding in giving brand managers directions for dealing with transgressing endorsers.