[6] Chou Chin-hua (周錦華), the boys' maternal grandmother, and the 7-year-old brothers moved to Taiwan amid the Chinese Civil War.

With Helen H. Huang (黃美倫), he has two daughters, Hui-lan (惠蘭) and Hui-yun (惠筠), and a son, Wan-an (萬安).

In 1993 he was appointed to the cabinet-level post of Chairman of the Overseas Chinese Affairs Commission and served as a member of the KMT Central Standing Committee.

He was speculated as a potential running mate for Lien Chan on the KMT ticket in the 2000 presidential elections until a sex scandal involving a mistress caused him to resign on 22 December 1999.

In January 2006, Chiang declared his candidacy as a KMT candidate for the Taipei Mayor,[13] but withdrew from the race in April, stating he did so for party solidarity.

In the 2008 Republic of China legislative election, John Chiang won re-election in his district of Taipei City North.

[19] Chiang Wan-an subsequently won the KMT primary in May 2015,[20] quickly gaining name recognition thanks in part to his chats with prospective voters as they waited for garbage trucks.