The mean lifetimes of the lowest energy 2+, 8+ and 9− states in 166Os have been measured using the recoil distance Doppler-shift method in conjunction with a selective recoil-decay tagging technique. These measurements extend studies into the most neutron-deficient mass region accessible to current experimental methods. The B(E2; 2+ → 0+) = 7(2) W.u. extracted from these measurements is markedly lower than those observed in the heavier even-mass Os isotopes. The 8+ and 9− states yield reduced transition probabilities that are consistent with single-particle transitions. While these values may indicate a departure from collective structure, the level scheme and the underlying nuclear configurations can also be interpreted in terms of a simple collective picture. This contrasting behaviour suggests an intriguing dichotomy in the description of heavy transitional nuclei.