Polyolefins represent the largest class of commodity materials due to their excellent material properties; however, they have limited pathways to chemical recycling and are often difficult to mechanically recycle. Here we demonstrate a new catalyst for the isoselective copolymerization of propylene and butadiene capable of favoring 1,4-insertion over 1,2-insertion while maintaining good molecular weights and turnover frequencies. This isotactic propylene copolymer with main-chain unsaturation was depolymerized to a telechelic macromonomer using an olefin metathesis catalyst and 2-hydroxyethyl acrylate. After hydrogenation, the telechelic macromonomer was repolymerized to form an ester-linked polypropylene material. This polymer shows thermal and mechanical properties comparable to linear low-density polyethylene. Finally, the telechelic macromonomer could be regenerated through the depolymerization of the ester-linked polypropylene material, which allows for the chemical recycling to macromonomer. This process provides a route to transform partially unsaturated polyolefins to chemically recyclable materials with similar properties to their parent polymers.