J. M. Coetzee criticizes the scholarship on apartheid for its apparent “indifference” to the “madness” of apartheid and for its limitation since it approaches apartheid “from outside.” Coetzee’s South African fiction should be regarded as his attempt to address these concerns: an inside view of the apartheid’s madness. It is suggested that the insanity of apartheid, in Coetzee’s fictional representation, lies in the social deformation that springs from its mode of intersubjective relatedness, its “pathological attachments.” It is through regulating individuals’ modes of relatedness and fashioning sadistic and masochistic subjects that the apartheid regime managed to reproduce and perpetuate itself. As such, apartheid represented the era of power struggles, subjection, and victimization. The present study employs the socio-ethical thought of Erich Fromm and combines it with the similar concerns of some other thinkers, to explore the themes of domination, subjection, and character distortion in Coetzee’s South African fiction in the context of apartheid. Coetzee’s novels, this study holds, are the fictionalized expression of his belief that apartheid distorted intersubjective relations, turned humans’ interactions into power struggles, and produced deformed, stunted subjects. It is such unproductive inter-human contacts that characterize the apartheid society as the manifestation of Coetzean insane society. Moreover, this study examines the continuing presence of these deformed subjects and distorted subjectivity in the post-apartheid South Africa and the violence that their presence occasions. The residual presence of character deformity and sadomasochistic intersubjectivity is a social reality of the new South Africa in Coetzee’s post-apartheid fiction; a material reality that diminishes the prospect of the promised sane society of post-apartheid era.