A simplified synthetic approach for the facile synthesis of polylactide graft copolymers utilizing both ring-opening metathesis polymerization (ROMP) and ring-opening transesterification polymerization (ROTEP) was reported. A comparison of the 1H NMR signals from the poly(DL-lactide) (PLA) initiation sites along the poly(1,5-cyclooctadiene-co-5-norbornene-2-methanol) (PCN) backbone and the terminating end groups revealed a slight excess of the terminal methine proton suggesting the graft copolymer may contain a small portion of PLA homopolymer. The calculated number-average molecular weight (Mn) of all the PLA chains in the system was 57 kg/mol. The size exclusion chromatography (SEC) data for the macroinitiator, PCN-332-10.9, showed a relatively symmetric, monomodal peak. Transmission electron microscopy (TEM) of thin sections of PCNL-332-10.9-95 revealed a phase-separated morphology consisting of spheroidal domains rich in poly-(1,5-cyclooctadiene) surrounded by a matrix of PLA.