Due to push and pull factors, millions of Chinese migrants fanned out into the Nanyang from the mid-1800s onward. The G1 (first generation) diasporic Chinese left China with a sojourner mentality, compelling their philanthropic action back to motherland China. As G1 diasporic Chinese and their second or third generation ethnic Chinese (G2, G3 …) eventually settled as nationals into various countries in Southeast Asia, their Confucian Chinese values were confronted, severely tested, remolded, and evolved as they assimilated and converged with the political, social, and economic circumstances of the times. With self-help and mutual aid philanthropy, they thrived and prospered in the Nanyang and were soon propelled to lead local communities. As they engendered gratitude to where they built their wealth, raised families, and honored ancestry in their resettled new homes, their loyalties, generosity, and philanthropy also began to shift away from China. This study investigates these traditions, ethos, and value systems through the lens of philanthropy.