MUSE, Myanmar — She was born to royalty in British colonial Burma, but rejected that life to become a cross-dressing warlord whose C.I.A.-supplied army established opium trade routes across the Golden Triangle. By the time of her death, last week at 90, she had led hundreds of men, endured prison and torture, generated gossip for her relationship with a film actress and, finally, helped forge a truce between ethnic rebels and the government.
Olive Yang grew up as one of 11 children in an ethnic Chinese family of hereditary rulers of what was then the semiautonomous Shan state of Kokang. According to relatives, she wore boys’ clothes, refused to bind her feet and frequently fell in love with her brothers’ romantic interests.
Concerned about their unconventional daughter, her parents arranged for her to marry a younger cousin. Shortly after she became pregnant, archives show, she left her husband to pursue a life among opium-trafficking bandits. Her son, Duan Jipu — named for the American jeeps Ms. Yang had seen in the Chinese city of Kunming during World War II — was raised by other family members.
Ms. Yang’s pursuit of a career as a militia leader and opium smuggler grew in part out of her desperation to escape traditional gender roles, her relatives said. “It was a temptation she couldn’t resist,” wrote her niece Jackie Yang in “House of Yang,” a family history published in 1997.
By age 25, she commanded hundreds of soldiers guarding caravans of raw opium on mules and trucks across the hills to the Thai border. Those trade routes served what would eventually become the world’s most productive opium-growing region, supplying raw ingredients for the heroin that was trafficked across the United States and Europe.
Ms. Yang partnered with remnants of the Chinese Nationalist troops who had been defeated by Mao’s Communists but continued to fight from havens in Burma. Intelligence dispatches at the National Archives in Yangon described her as a menace to the peace.
The Nationalist troops had won support from the C.I.A. because of their shared interest in stemming the spread of communism during the early stages of the Cold War. The covert plan, called Operation Paper, included an agreement by which American weapons were airlifted to Southeast Asia using planes owned by the C.I.A., Alfred W. McCoy wrote in his 1972 book, “The Politics of Heroin,’’ as the Nationalists and Ms. Yang’s troops financed their operations through opium sales.
The C.I.A.-supplied arms found their way into Ms. Yang’s hands in 1952, as documented by the Burmese government in a complaint submitted at the United Nations General Assembly the following year. Ms. Yang’s army was observed traveling across the border to an airfield in Thailand, where an unmarked C-47 aircraft arriving from Taiwan, the seat of the Chinese Nationalist government, was reported to have unloaded weapons.
Shortly thereafter, Ms. Yang was intercepted by the Burmese authorities while traveling by car from the Thai border with her deputy, Lo Hsing Han. She spent five years in prison in Mandalay, on charges that she helped Chinese Nationalist soldiers illegally cross the border into Burma. It was the first of many imprisonments for Ms. Yang and Mr. Lo.
Mr. Lo would go on to earn the designation “kingpin of the heroin traffic in Southeast Asia,” by United States drug enforcement officials, after striking a deal with the Burmese military government that allowed him to resume trading in opium in return for assisting government forces against rebel forces.
After her older brother Edward abdicated in 1959, along with dozens of other hereditary rulers in Shan state, Ms. Yang took control of his former army, becoming the de facto ruler of the territory. She also, according to her relatives, entered into a relationship with a Burmese movie actress, Wah Wah Win Shwe, lavishing her with gifts and adding her name to the deed of her house in Yangon.
Ms. Yang’s family considered them a couple, though in an interview in 2015, Ms. Win Shwe, who still lived in a house on Ms. Yang’s former property, denied an affair. In any case, the arrangement came to an abrupt end in 1963, when Ms. Yang was arrested by police officials under Gen. Ne Win, who had seized power in Burma the year before. She spent six years in Yangon’s Insein Prison, where she reportedly endured torture.
Her career took another turn in 1989, when she was in her 60s. Retired as a warlord but respected among the ethnic rebel groups, Ms. Yang was recruited by the Burmese government’s chief of intelligence, Khin Nyunt, along with her former colleague Mr. Lo, to help negotiate peace agreements for the government. The agreement struck with Ms. Yang’s distant relative Peng Jiasheng and his Kokang rebel force, the Myanmar National Democratic Alliance Army, largely held until new fighting broke out in 2009.
Confined to a wheelchair, Ms. Yang spent her twilight years in relative obscurity, living in the care of her stepson and his militiamen in a compound in Muse. Visited there not long after she had a stroke in 2015, Ms. Yang said she was happy to be living surrounded by deferential soldiers. When shown a photograph of Ms. Win Shwe at her home, Ms. Yang responded with a knowing smile and a devilish laugh. With a Chinese cigarette in her hand, she said, “That whole property was mine.”
Ms. Yang, who died on July 13, is survived by two younger sisters and her son. None of her immediate relatives remain in Kokang. Ms. Yang’s eventual tomb, built for her with the help of one of her former soldiers, stands near Muse, just outside Kokang.
“It’s very sad for all of Kokang,” said the former soldier, Liu Guoxi, reached by phone as he was preparing for the funeral. “We have all come to say farewell to our leader.”
Olive Yang (Chinese: 楊金秀; pinyin: Yáng Jīnxiù; also known as Yang Kyin Hsiu, nicknamed Miss Hairy Legs) was the half-sister of Sao Edward Yang Kyein Tsai, the saopha (chief) of Kokang, a state in post-independent Burma from 1949 to 1959. She received an education at Lashio's Guardian Angel's Convent School. At the age of 19, she organized ethnic Kokang forces, nicknamed the Olive's Boys, an army of over a thousand soldiers and consolidated control of opium trade routes from the highlands to lowlands. She dominated Kokang's opium trade from the end of World War II to the early 1960s. In the 1950s, after the Nationalist defeat and their subsequent expulsion from mainland China, she partnered with the Kuomintang to establish opium trade routes along the Golden Triangle (Southeast Asia).
From 1948 to 1950, she was married to Twan Sao Wen, the son of Tamaing's chieftain, and had a son, Duan Jipu (段吉卜), in 1950. Her son is a teacher in Chiang Mai, Thailand.
From the 1950s to the mid-1960s, she was the commander of the Kokang Kakweye (People's Defense Forces). She was a prominent figure in opium trafficking and gold trading. She was arrested in 1962, along with her brother Jimmy, a member of parliament in Yangon, by Burmese authorities, to remove them from power and place Kokang territory under Burmese administration. She was imprisoned at Insein Prison and released in 1968.
Yang was known to be a bisexual who carried on affairs with film actresses and singers, including Wah Wah Win Shwe (ဝါဝါဝင်းရွှေ). In the late 1980s, she was recruited by Khin Nyunt to help broker ceasefires in Burma with ethnic rebel groups.