The majority of wind damage is to building envelope components. Large eddy simulations (LESs), which can predict flow fields at high resolution, have significant potential for analyzing component loads. This study aims to (1) demonstrate that LESs can elucidate flow phenomena behind peak pressure loads, and (2) quantitatively compare LESs to full-scale measurements performed on the roof of the 184 m tall Space Needle. The simulations revealed unsteady flow features responsible for pressure signals observed in separation regions and shear layers. Furthermore, predictions for fluctuation pressure coefficients were quantitatively representative of field data. The main discrepancy observed was a more pronounced variability of measured, compared to simulated, shear layer peak pressures. Detailed measurements of the incoming wind field would be needed to further investigate this discrepancy. The results demonstrate the value of joint field measurements and LESs for studying wind effects.