Data from this current study emerged from a larger study on contemporary leadership practices at historically Black colleges and universities (HBCUs). One of the themes that emerged focused on unsuccessful leadership practices among HBCU presidents. Although this article contextualizes this theme, it is important to underscore that it is not the intent of the authors to approach this topic from a deficit based-perspective but rather an asset-based one. Specifically, through the findings, discussion, and implications, we hope that this article will promote and facilitate successful practices of leadership among HBCU presidents, which will help to contribute to the survival and sustainability of these noble institutions.