The transformation of a 30 m long timber pedestrian bridge into a wobbly (laterally swaying) bridge with a dramatically reduced first lateral modal frequency has been monitored by seven annual, multi-sensor surveys. This evidence, in combination with analysis of the wind record, observations of local damage and evidence of wind-induced excitations from other bridges, is used to present a multi-stage scenario of the extraordinary structural weakening of our study bridge in only a few years. Our analysis is constrained by observations of asymmetric damage (longitudinal splitting cracks around metallic connections along the south side of the deck, not explained by ordinary, essentially symmetric lateral oscillations) and over-threshold analysis of strong northerly wind events, including gusts. The proposed scenario is that an unexpected for the area icing event took advantage of construction vicissitudes and produced damage that reduced the lateral stiffness of the bridge, especially of the arch superstructure. In addition, strong winds sharing common direction with gusts produced a combination of semi-static lateral bending and of dynamic oscillations, leading to numerous cycles of asymmetric high amplitude lateral deflections producing tensile stress normal to grain, cracks localized in connections, and fatigue. The vertical stiffness of the bridge was only slightly affected.