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This article, written to commemorate the 5th anniversary of Sidney J. Blatt's death, addresses the legacy of his work on autonomy and relatedness as fundamental dimensions in normal and disrupted personality development. We begin the article by exploring what it was about Blatt's contributions in this area that made it so resonant and valuable to the wide community of clinicians and academics. The 2nd part of the article reflects on how his thinking has influenced our own work concerning the origins of human subjectivity and its role in normal and disrupted development. We argue that our views concerning the role of attachment and mentalizing in developing the capacity for epistemic trust and salutogenesis are highly organized around Blatt's conception of the human dilemma arising from the dialectical needs for relatedness and an autonomous, agentive self. We also discuss the similarities in our views concerning the parallel between normal developmental processes and the therapeutic process, with a focus on the importance of experiences of mutuality and understanding versus separation and misunderstanding in both.