The paper investigates South African courts’ treatment of discriminatory testamentary bequests in the pre- and post-constitutional eras. It shows a change in judicial attitude towards such bequests from an accommodating, tolerant stance, purportedly founded on South Africa's Roman-Dutch common law, during the pre-constitutional era to a firm normative approach with a focus on equality and non-discrimination during the post-constitutional years. The Article assesses critically this post-constitutional approach against precedent and scholarship from Common Law and Civil Law jurisdictions and asks whether, given the mixed nature of its legal system, the current South African position in regard to such bequests achieves a good fit between the Common Law and Civil Law.