Summary: The metallocenes rac‐C2H4(Ind)2ZrCl2 ( 1 ), rac‐Me2Si(Ind)2ZrCl2 ( 2 ), and rac‐Me2Si(2‐Me‐benze]Ind)2ZrCl2 ( 3 ) efficiently copolymerize propene and 5‐vinyl‐2‐norbornene (VNB). 1 and 2 give a high VNB content and high productivities, whereas 3 gives moderate incorporation. Surprisingly, precatalysts 1 and 2 , which have very closely related structures, showed very different reactivities toward VNB, with 1 having a greater affinity for VNB than for propene. The copolymers are quantitatively converted into polyolefins with polar functionalities.