As employee careers have evolved from linear trajectories confined within 1 organization to more dynamic and boundaryless paths, organizations and individuals alike have increasingly considered reestablishing prior employment relationships. These “boomerang employees” follow career paths that feature 2 or more temporally separated tenures in particular organizations (“boomerang organizations”). Yet, research to date is mute on how or to what extent differences across boomerang employees’ career experiences, and the learning and knowledge developed at and away from boomerang organizations, meaningfully impact their performance following their return. Addressing this omission, we extend a careers-based learning perspective to construct a theoretical framework of a parsimonious, yet generalizable, set of factors that influence boomerang employee return performance. Results based on a sample of boomerang employees and employers in the same industry (professional basketball) indicate that intra- and extraorganizational knowledge construction and disruptions, as well as transition events, are significantly predictive of boomerangs’ return performance. Comparisons with 2 matched samples of nonboomerang employees likewise suggest distinctive patterns in the performance of boomerang employees.