In this Article, we explore the potential of triarylmethyl (TAM) oligomers as devices for organic molecular spintronic applications. We use the Landauer formalism to compute global spin transport and local current analysis to understand transport at finite bias voltages within the nonequilibrium Green’s function framework and using density functional theory calculations. Important variations of the total spin current are observed in chlorinated TAM dimers as a function of the electronic structure in the device. On the other hand, the spin-resolved local transport mechanism and the geometry of the nanodevice are found to depend weakly on the electronic structure, even at relatively high voltages. Such dimers could potentially be used in transistor applications. Further, devices based on chlorinated TAM monomers are shown to possess strong differential spin-transport properties at low bias voltage, a property that could be used for spin filtering.