Cloud structure and evolution of Mesoscale Convective Systems (MCSs) retrieved from the Tropical Rainfall Measuring Mission Microwave Imager (TRMM TMI) and Precipitation Radar (PR) were investigated and compared with some pioneer studies based on soundings and models over the northern South China Sea (SCS). The impacts of Convective Available Potential Energy (CAPE) and environmental vertical wind shear on MCSs were also explored. The main features of MCSs over the SCS were captured well by both TRMM PR and TMI. However, the PR-retrieved surface rainfall in May was less than that in June, and the reverse for TMI. TRMM-retrieved rainfall amounts were generally consistent with those estimated from sounding and models. However, rainfall amounts from sounding-based and PR-based estimates were relatively higher than those retrieved from TRMM-TMI data. The Weather Research and Forecasting (WRF) modeling simulation underestimated the maximum rain rate by 22% compared to that derived from TRMM-PR, and underestimated mean rainfall by 10.4% compared to the TRMM-TMI estimate, and by 12.5% compared to the sounding-based estimate. The warm microphysical processes modeled from both the WRF and the Goddard Cumulus Ensemble (GCE) models were quite close to those based on TMI, but the ice water contents in the models were relatively less compared to that derived from TMI. The CAPE and wind shear induced by the monsoon circulation were found to play critical roles in maintaining and developing the intense convective clouds over SCS. The latent heating rate increased more than twofold during the monsoon period and provided favorable conditions for the upward transportation of energy from the ocean, giving rise to the possibility of inducing large-scale interactions.