In order to clarify the cracking and failure behavior of gray cast iron brake blocks that are used for the railway applications, macro- and micro observations regarding the cracks and the micro-structure of the used brake blocks were examined. Three brake blocks, which have different degrees of hot spots and cracking during the actual application, were selected for testing. In addition, a thermal-mechanical coupled finite element analysis (FEA) was applied to calculate the temperature and the stress field in the brake blocks during braking. As a result, it was observed that surface cracks were initiated at the hot spots and propagated into the matrix. From the observation of dispersed graphites close to the crack path, it can be said that the deterioration of materials due to the frictional heat of braking made it easy to initiate cracks at the hot spot. The hardness of the brake block was recommended to be under 85 by the Rockwell B scale in order to prevent hot spots and crack initiation. From the FEA, the procedure for the occurrence of hot spots and cracks was successfully simulated by assuming the surface roughness on the slid surface of the brake block.