Late Mississippian and earliest Pennsylvanian trilobite faunas of North America are dominated by the Paladin and Kaskia clades. Phylogenetic analysis of middle Carboniferous species of these clades demonstrates the close ancestral relationship between these groups. The Kaskia clade consists of eight species: K. chesterensis Weller, 1936, K. osagensis (Cisne, 1967), K. longispina (Strong, 1872), K. wilsoni (Walter, 1924), K. genevievensis (Walter, 1924), K. rosei (Cisne, 1967), K. gersnai n. sp., and K. rollinsi n. sp. Kaskia Weller, 1936 ranges from late Osagean to middle Chesterian (early Visean-early Serpukhovian) and is restricted to cyclothemic shelf and nearshore deposits. Species of Kaskia appear to have evolved in areas of shallow water and high environmental stress. The Paladin clade consists of 12 species including previously named species P. morrowensis (Mather, 1915), P. girtyianus Hahn and Hahn, 1970, P. rarus Whittington, 1954, P. helmsensis Whittington, 1954, and P. moorei (Branson, 1937). New species belonging to this clade are Paladin moorefieldensis n. sp., P. pleisiomorphus n. sp., P. imoensis n. sp., P. mangeri n. sp., and P. wapanukaensis n. sp. This group ranges from the early Chesterian to early Morrowan (late Visean-late Bashkirian). Species of Paladin appear to be confined to outer shelf shelf-edge and off-shelf facies where presumably deeper water environments existed. This is manifested in their paleogeographic distribution, which is paleoenvironmentally controlled.