Mentorship may offer protégés numerous benefits including improved self-esteem, increased interest in research, and/or enhanced productivity. Without proper planning, reflection, and evaluation, however, mentorship programs may result in undesirable consequences. In this paper we describe a mentorship program designed to improve psychosocial support and professional development for residents, that while initially successful, was terminated due to perceptions of inequity that led to strife among residents and ultimately created a toxic learning climate. Leader-member exchange theory provides a lens through which to view our program’s failure and to offer some potential solutions to mitigate such challenges for other programs. Leader-member exchange theory focuses on the importance of relationships, communication, and awareness of biases to optimize interactions between dyads such as a mentor and a protégé. We highlight opportunities during the stranger, acquaintance, and mature partnership phases that could have helped to save a residency mentorship program.