Structural aspects as well as the stability and reactivity of the CHBr2+ dication are studied both experimentally and theoretically. Translational energy distributions of the CHBr+ products from charge transfer between CHBr2+ and Kr indicate that the dication exists in two isomeric forms, H-C-Br2+ and C-Br-H2+. In the reaction of CHBr2+ with H-2, the dominant channel corresponds to proton transfer leading to CBr+ + H-3(+). Other reaction channels involve the formation of the intermediates CH3Br2+ and CH2BrH2+, respectively. Both of the latter dications can either lose a proton to form CH2Br+ or undergo a spin-isomerization followed by cleavage of the C-Br bond. The proposed mechanisms are supported by DFT calculations and deuterium labeling experiments.