Organic luminescent radicals have attracted increasing attention because of their unique doublet emission mechanism. This article summarizes recent progress in carbazole-substituted tris(2,4,6-trichlorophenyl)methyl (TTM) radicals, focusing on strategies to improve photostability and to control emission wavelength. In particular, we discuss how donor substitution and dendritic structures influence excited-state character and photophysical properties. By introducing a model that incorporates electron–electron repulsion effects, we provide a conceptual explanation for unexpected spectral shifts observed upon increasing the number of carbazole units. The relationship between electronic structure, stability, and emission efficiency is highlighted to offer design guidelines for next-generation radical-based luminophores. Furthermore, the potential of water-soluble luminescent radicals for dual fluorescence and magnetic resonance imaging is briefly discussed.