The rapid polar sea ice retreat and its drivers are challenging and still unresolved questions in climate change research. In particular, the relationship between near-surface wind speed and sea ice extent remains unclear for two main reasons: (1) observed wind speeds over Polar Regions are very sparse, and (2) simulated winds by climate models are dependent on subjective parameterizations of boundary layer stratification, ultimately leading to large uncertainty. Here, we use observation-based data (passive microwave sea ice concentration and six different reanalysis datasets) together with output from 26 climate models (from the CMIP5 archive) to quantify the relationships between near-surface wind speed and sea ice concentration over the past 40 years. We find strong inverse relationships between near-surface wind speed and sea ice concentration that are consistent among the six reanalysis datasets. The poleward wind component is particularly increasing in years of reduced sea ice concentration, which contributes to the enhancement of the atmospheric (surface oceanic) poleward heat flux by up to 24 ± 1% (29 ± 2%) in the Arctic and 37 ± 3% (51 ± 3%) in the Antarctic seas, therefore boosting the impact of polar sea ice loss and contributing to polar amplification of climate warming. In addition, our results show a marginal contribution of the dynamical (pushing/opening/compacting) effects of wind on sea ice compared to the thermodynamic effects which in turn play a lower role than the associated change in local surface Autumn-Winter turbulent and Spring-Summer radiative fluxes. Climate models generally produce similar results but with lower magnitude, and one model even simulates the opposite relationship wind/sea-ice. Given the rapid changes in polar climate and the potential impacts on the mid-latitudes, it is urgent that model developments make use of evidence from satellite observations and reanalysis datasets to reduce uncertainties in the representation of relationships between polar winds and sea ice.