A drill bit that includes a bit body having one or more blades extending therefrom and a plurality of cutters secured to the one or more blades. One or more rolling elements are positioned on the bit body, each rolling element having a cylindrical bearing portion defining a rotational axis. Each rolling element is rotatably coupled to the bit body about the rotational axis within a corresponding pocket defined in the bit body and a locking pin secures the rolling element within the pocket. One or more internal bearing surfaces of the pocket engage the cylindrical bearing portion and the pocket partially encircles the cylindrical bearing portion while leaving a full length of the rolling element exposed.