This paper describes controlled ring-opening metathesis polymerizations (ROMP) of norbornene derivatives that bear photoreactive o-nitrobenzyl ester (NBE) moieties. Termination reactions have frustrated previous reported attempts to execute controlled radical polymerizations with nitrobenzyl ester-containing acrylate derivatives. We therefore prepared new NEE-containing norbomene C derivatives, and found that polymerization with Grubbs's ruthenium carbene catalysts led to complete consumption of monomer in minutes to hours and yielded polymers with predictable molecular weights. We also demonstrate the preparation of NBE-containing block copolymers and show through UV irradiation of these polymers in solution and in thin film that the NBE moieties remain photoreactive.