The genus Rumex is a unique member of the Polygonaceae (Buckwheat) family of plants. A source of intrigue for Rumex lies in the diversity of the sexual systems associated with the subgenera, species, and subspecies within this genus. Four previously circumscribed subgenera, some 200 species, and a number of subspecies comprise the collective Rumex genus. These species exhibit monoecious, dioecious, synoecious (hermaphroditic), and polygamous sexual systems. Moreover, some of the dioecious species contain sex chromosomes, a phenomenon that is very rare in angiosperms. Apart from the confirmed morphological and phytogeographical distinctions, two of the four described subgenera, Acetosa and Acetosella, are distinctive in their exhibited sex- chromosome systems. For this study, we used three chloroplast markers, rbcL, trnH-psbA, trnL-F, and dense taxon sampling, to reconstruct a molecular phylogeny for Rumex.The reconstructed phylogeny for this work resolves six major clades and one large grade in Rumex. In addition, the species with known dioecious sexual systems derived from unique sex chromosome systems are resolved in two different clades nested within “the dioecious clade”. These results suggest that the species with divergent sexual systems are more closely related to each other than to other species comprising the rest of the Rumex genus. Furthermore, some species with known synoecious sexual systems are resolved in a single clade which is also nested within “the dioecious clade”. These results imply a possible reversal occurring over time which suggests the highly plastic nature of sexual systems among Rumex species.