To enhance the strength while retaining the ductility of triptycene polyester, triptycene polyester/SWCNT nanocomposites were prepared. First, two different types of triptycene polyesters containing triptycenes that differ in size were synthesized and their mechanical and thermal characteristics were studied. Thermal analysis showed that the polyester containing the larger triptycene posed as a bigger hindrance factor to polymer chain-packing, resulting in lower crystallinity. Although the presence of triptycene interfered the packing of polymer chains, the increased size and amount of triptycene enhanced the thermal stability of the polymer. For the smaller sized triptycene-polyester/SWCNT composites, higher SWCNT content increased the stiffness and strength of the composite, but at the expense of the ductility. The increase in SWCNT content in the larger-sized triptycene polyester/SWCNT composites somewhat decreased the stiffness as well as the ductility of the polymer.