Damage in bearings is closely associated with the presence of microstructural alterations, known as white etching areas (WEAs) and white etching cracks (WECs). One of the main reasons for the creation of these microstructural alterations is the presence of defects in the material, such as non-metallic inclusions. Manganese sulfides and aluminum oxides are widely reported in the literature as the most common types of non-metallic inclusions found in bearing steels. This study classifies 280 non-metallic inclusions in an investigated bearing steel according to several criteria: bonded/debonded with the matrix, size, shape, orientation angle, depth below the raceway surface, and chemical composition. Contrary to the findings in the literature, this investigation reports that the chemical composition of the inclusion (MnS + Al₂O₃) is of secondary importance when considering factors for damage initiation. The orientation of the microstructural alterations is observed to coincide with the high-stress regions, indicating a relation between the formation of butterfly wings and the white etching crack. In our investigation, butterfly wings typically exhibit a 45-degree pattern originating from the non-metallic inclusions. Conversely, the white etching crack starts from the non-metallic inclusion at a shallower angle in correspondence to the raceway. This can be attributed to the stress state, which corresponds to a region where extensive white etching cracks are formed. In conclusion, the microstructural observations demonstrate that the state of non-metallic inclusion—i.e., whether they are bonded or not to the steel matrix—plays an essential role in initiating rolling contact fatigue damage.