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In this article, malignant self-regard (MSR) is reviewed, and its research effort is briefly discussed. It is noted that an expansion of MSR's construct validity is required. The article then focuses on the gaps in the literature between perfectionism, grit, and MSR. We introduce an object-relations account of perfectionism and depressive personality, which predicts a positive association between MSR and perfectionism. Then, we review the literature on grit's relationship with perfectionism, achievement, and depression, which predicts MSR will be negatively associated with grit. Inferential analysis of the online sample (n = 309) is consistent with expectations. As MSR increases, (a) grit declines, (b) rigid perfectionism stays relatively stable, and (c) self-critical and narcissistic perfectionism rises significantly. In the discussion, attention is dedicated to the clinical implications of these findings. We then discuss ways to navigate the clinical complexities that arise from this situation that can be applied in dynamic and nondynamic treatment models. We then close with important limitations and outline future research directions for MSR.