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Taipei Mayor Chiang Wan-an with his team after the annual Minan civilian defense drill, which this year focuses on the response from various agencies and volunteer groups if under attack by China in front of Taipei City Hall in Taipei, Taiwan May 4, 2023.ANN WANG/Reuters

Chiang Wan-an, the boyish-looking mayor of Taiwan’s capital, Taipei, has perhaps the most interesting backstory of any politician in this Asian democracy. He is known as the great-grandson of the island’s first and most controversial president: Chiang Kai-shek.

Mr. Chiang, 45, is already being eyed as a possible presidential candidate in Taiwan for the Nationalist Party, or the Kuomintang, whose name was once synonymous with power on this self-governing island claimed by China. The Kuomintang has lost the past three presidential elections to the China-skeptical Democratic Progressive Party – an unprecedented streak of failures.

Former president Ma Ying-jeou, the last Kuomintang leader to win the president’s office, in 2008 and 2012, said in a recent interview with The Globe and Mail that he thought Mr. Chiang would make a good candidate once he has more experience under his belt.

Many presidential candidates in Taiwan get their start in municipal politics. Mr. Ma noted he himself was once mayor of Taipei. He said Mr. Chiang, who was elected twice for the Kuomintang to Taiwan’s legislature, could be ready in several election cycles.

“He, by and large, is following my path,” Mr. Ma said of the mayor. “I hope he could be successful in getting a second term in Taipei City and then run for president,” he said. “He has a good chance. He’s popular – very popular.”

Mr. Chiang declined an interview, saying through staff he was not talking to foreign journalists because he was busy with city council business.

That didn’t stop him from embarking on a work trip in September to New York, Boston and Philadelphia, where he gave U.S. policy-makers a chance to watch him in action. The United States is Taiwan’s most important ally.

Mr. Chiang, whose party faces criticism that it’s too friendly with authoritarian China, used an address at Harvard University to defend Taiwanese democracy, comparing it to “spicy hot pot” cuisine in Taipei. “It’s not perfect. Its spices may make you sweat, but you keep coming back for more,” he said in September.

“We believe that democracy, freedom and rule of law provide the bedrock for sustainable prosperity,” he said. “Our hot pot remains ever fresh and never runs dry.”

Should Mr. Chiang seek and win the presidency, it would vault Taiwan’s political dynasty, the Chiang family, back into the international spotlight.

The elder Chiang Kai-shek was still in charge of Taiwan in 1970 when then-prime minister Pierre Trudeau cut off Canada’s formal diplomatic relations with the island and established ties with the People’s Republic of China.

China’s Communist Party considers Taiwan a breakaway province despite the fact it has never ruled the island, where Chiang Kai-shek’s defeated Nationalist forces retreated after losing the Chinese civil war more than 70 years ago. China still seeks to annex Taiwan and has not ruled out using force. It has staged military exercises near the island more than 10 times since 2018.

The Canadian government soured on Chiang Kai-shek after lending him as much as $60-million during the Nationalist forces’ civil war with the Communists, a fight he lost in 1949. In a May, 1949, letter to Ottawa, Thomas Clayton Davis, Canada’s then-ambassador to China, spoke derisively of Chiang, who at one point in false humility had declared himself unworthy and unsuited for the post of president of China. “As events have developed it is now apparent that in actuality he sized himself up with a remarkable degree of accuracy,” Mr. Davis wrote.

Chiang Kai-shek ruled Taiwan, formally called the Republic of China, with an iron fist until his death in 1975; the island peacefully transitioned to democracy in the late 1980s and 1990s. Since then, Taiwan’s political system has been dominated by the Kuomintang (KMT), leader of what’s called the blue camp, and the DPP, which heads the green camp. The KMT favours more co-operation with China, has traditionally encouraged closer ties with Beijing and identifies with its Republic of China (ROC) past. The DPP, conversely, has traditionally championed a more distinct Taiwanese identity and Taiwanese nationalism.

Lev Nachman, an assistant professor in the Graduate Institute of National Development at National Taiwan University, said the Taipei mayor’s family history would serve him well if he were to pursue higher office.

“Because he is sort of the new face of the Chiang family, I think there is a non-trivial number of blue voters in Taiwan who look at him as sort of the next generation holding the Republic of China torch,” Dr. Nachman said. “I think that’s very powerful for blue voters here.”

Mr. Chiang’s father is John Chiang, a former foreign minister and vice-premier of Taiwan who in 2002 was recognized by the Taiwanese government as the illegitimate son of the late president Chiang Ching-kuo, who was Chiang Kai-shek’s son. Back then the government accepted his application to change his family name from Chang to Chiang.

Dr. Nachman predicts rival parties will question Mr. Chiang’s bloodline. “When he eventually runs for president, which I anticipate he will one day, I absolutely believe that there will be a deep dive into his family background,” he said. “That’s because it will be fodder for the DPP to say he’s not truly the great-grandson of Chiang Kai-shek.

Mr. Chiang’s political rivals think he will be a contender.

DPP legislator Fan Yun said she believes the Taipei mayor has ambitions for the presidency. “He is a rising star.” She said: “He’s very cautious.”

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