We have carried out a search for massive white dwarfs (WDs) in the direction of young open star clusters using the Gaia DR2 database. The aim of this survey was (1) to provide robust data for new and previously known high-mass WDs regarding cluster membership, (2) to highlight WDs previously included in the initial final mass relation (IFMR) that are unlikely members of their respective clusters according to Gaia astrometry, and (3) to select an unequivocal WD sample that could then be compared with the host clusters' turnoff masses. All promising WD candidates in each cluster color-magnitude diagram were followed up with spectroscopy from Gemini in order to determine whether they were indeed WDs and derive their masses, temperatures, and ages. In order to be considered cluster members, white dwarfs were required to (1) have proper motions and parallaxes within 2{sigma}, 3{sigma}, or 4{sigma} of those of their potential parent cluster based on how contaminated the field was in their region of the sky, (2) have a cooling age that was less than the cluster age, and (3) have a mass that was broadly consistent with the IFMR. A number of WDs included in current versions of the IFMR turned out to be nonmembers, and a number of apparent members, based on Gaia's astrometric data alone, were rejected, as their mass and/or cooling times were incompatible with cluster membership. In this way, we developed a highly selected IFMR sample for high-mass WDs that, surprisingly, contained no precursor masses significantly in excess of ~6M_{sun}_.