Benzonorbornadiene polymers synthesized by ring opening metathesis polymerization (ROMP) are typically prone to oxidation at the benzylic/allylic position under ambient conditions. Accordingly, the use of benzonorbornadiene polymers in practical applications has remained limited. In this manuscript, we report the synthesis of poly(benzonorbornadiene) polymers using a strategic blend of benzyne chemistry and ROMP. Through a comparative study, we show that substitution at the benzylic/allylic position prevents oxidative deformation, yet does not inhibit polymerization by common ruthenium catalysts with good control over molecular weight dispersity. We expect the benzyne/ROMP reaction sequence will allow easy access to air-stable benzonorbornadiene polymers for various applications.