Uncertainty exists in signal-matching techniques. The quake and damping obtained may not be the actual response of the soil. In this paper, the final sets, strain gauge readings, pile driving analyzer, and Case pile wave analysis program of 12 high-capacity long H-piles at the end of initial driving as well as two of them at restrike are studied. Measured and deduced data show that the soil response underneath the pile toes has limited movement and yielding despite the piles being set using very heavy hammer rams and large ram drops. The quake and damping decrease with increased shearing strain and shearing stress, but are influenced by pile whipping, rebounded stress wave, and load-transfer mechanism. The lumped Case damping factor decreases with increased side resistance to total resistance ratio. This factor can decrease or increase with time due to changes in the load-transfer mechanism after set-up, thus affecting the proportion of viscous damping of soil along the pile shaft and at the pile toe. A Case damping model is proposed that approximates the lumped Case damping factor as the sum of hysteretic damping of the pile and viscous damping of the surrounding soil. The effects of variation in load distribution and set-up along the pile shaft in layered soils and incomplete mobilization of soil at the pile toe on the Case damping factors are explained.