Aromatic polyamides and polyimides were synthesized from 4,4’-diaminotriphenylmethane (DA-TPM) for studying their solubility, thermal, and mechanical properties. The polymers were found to be soluble in amide solvents and pyridine, and this could be attributed to the practically free rotation of the polymer chain segments around the bridging group within the DA-TPM and the effect of its pendant phenyl ring. The polyimides and polyamides exhibited well-distinguished glass transition in the range of temperatures, which is typical for flexible-chain polymers. For the polyimides, significant differences in solubility and mechanical properties were observed between the samples prepared by chemical and thermal imidization of poly(amic acids). Thermal imidization brought about remarkably less soluble brittle films.