In 1996, Chiang's illegitimate son Chiang Hsiao-tzu suffered a brain hemorrhage while giving a lecture in Beijing. Despite returning to Taiwan to undergo therapy, he passed on some months later. The same year, Chiang's third son Chiang Hsiao-yung lost his battle with esophageal cancer.
1996 年，庶出的蔣孝慈在北京講學時發生腦溢血，返台治療幾個月之後仍不幸過世；同一年，三子蔣孝勇也因罹患食道癌，離開人世。