The great anatomical diversification of paired fins within the Actinopterygii (ray-finned fishes) can be understood as a suite of evolutionary transformations in design. At a broad taxonomic scale, two clear trends exist in the morphology of the anteriorly situated pectoral fins. In comparing basal to more derived clades, there are general patterns of (i) reorientation of the pectoral fin base from a nearly horizontal to more vertical inclination, and (ii) migration of the pectoral fin from a ventral to mid-dorsal body position. As yet, the functional significance of these historical trends in pectoral fin design remains largely untested by experiment. In this paper we test the proposal that variation in pectoral fin structure has an important influence on the magnitude and orientation of fluid forces generated during maneuvering locomotion. Using digital particle image velocimetry for quantitative wake visualization, we measure swimming forces in ray-finned fishes exhibiting the plesiomorphic and apomorphic pectoral fin anatomy. Our experiments focus on rainbow trout (Oncorhynchus mykiss), a lower teleost with pectoral fins positioned ventrally and with nearly horizontally inclined fin bases, and bluegill sunfish (Lepomis macrochirus), a relatively derived perciform fish with more vertically oriented pectoral fins positioned mid-dorsally on the body. In support of hypotheses arising from our prior wake studies and previously untested models in the literature, we find that the pectoral fins of sunfish generate significantly higher forces for turning and direct braking forces closer to the center of mass of the body than the pectoral fins of trout. These results provide insight into the hydrodynamic importance of major evolutionary transformations in pectoral fin morphology within the Actinopterygii.