Portugal celebrated 50 years of democracy a few weeks ago on the 25th of April. On that day in 1974, a military coup ended 48 years of authoritarian rule under the Estado Novo. The almost bloodless uprising was called the "Carnation Revolution" because blossoms were placed in the barrels of soldiers' guns. A major driver was the unpopular Portuguese Colonial War that had lasted 13 years, a costly counterinsurgency effort against armed independence movements in Portugal's African colonies of Angola, Guinea and Mozambique.

The Carnation Revolution swiftly led to a wave of decolonization in Africa, and with Goa having been annexed by India in 1961, and East Timor effectively abandoned in 1975, the Portuguese Empire that started in 1415 was down to a tiny territory in Asia: Macau.
Macau was a unique case because of the complicated issue of sovereignty stretching back to the establishment of the trading post in China in the 16th century. It wasn't until 1783 that Portugal claimed an equal (if not greater) stake in Macau's sovereignty, and in 1849, in the wake of the First Opium War between China and Britain, the Portuguese proclaimed de facto sovereignty over Macau. There would be more diplomatic twists and turns until the People's Republic of China (PRC) was established in mainland China by the Chinese Communist Party (CCP). The Nationalist Kuomintang retreated to Taiwan, and for the CCP, Taiwan then became the top territorial priority ahead of both Hong Kong and Macau.

Mainland China went into the Cultural Revolution in the 1960s, which meant that all political energies were focused internally. Nevertheless, the growing influence of communist China in Macau contributed to the "1, 2, 3 incident" on December 3, 1966 that saw martial law being declared and at least eight people killed by the police and the Portuguese Army. As a result of the backlash, the Portuguese government issued an apology in 1967 and formally recognized Macau
as a Chinese territory. In fact, the Portuguese foreign minister at the time, Alberto Franco Nogueira, referred to Portugal's role in Macau as “zeladores de um condomínio sob supervisão estrangeira” (caretakers of a condominium under foreign supervision). Diplomatically, Portugal still recognized the Kuomintang-led Republic of China (ROC) in Taiwan, but after the "1, 2, 3" episode pro-Beijing trade unions and business leaders started gaining more political power. This led to the closure of the ROC diplomatic mission as well as Kuomintang-run schools in Macau.
As "a Chinese territory under Portuguese administration", Macau was not listed as a colony by the United Nations, and while China continued to criticize Portugal's colonial wars in Africa and provide support to the independence movements, it remained silent on Macau.
Indeed, after the Carnation Revolution of 1974, the Portuguese government tried twice to return this "condominium under foreign supervision" back to China, then ruled by paramount leader Mao Zedong. However, the Chinese were in no rush and turned the Portuguese down, saying that the time wasn't right, even after Portugal formally switched diplomatic recognition to communist China in 1979. Despite reports in Western media that China "didn't want" Macau, there were good reasons why the Chinese decided to play for time:
Their top territorial concern was recovering Taiwan and finishing the civil war that ended in 1949 only because the communist forces were in no position to continue the fight to the island.
Macau was still useful for trade purposes. Under Portuguese administration, Macau would not be affected by blockades and boycotts targeting mainland China and it was, in fact, a major trading zone during the Korean War in 1950-53.
China was wary of the new Portuguese government that had started to alarm other European countries and the US with its pro-Soviet tendencies; ironically, communist China had antagonistic relations with the Soviet Union at the time.
Hong Kong was of far greater importance economically and diplomatically than Macau, and also far more complicated as the British, unlike the Portuguese, did not seem to be in any hurry to leave. Taking back Macau too quickly risked destabilizing Hong Kong.
The Chinese finished their negotiations with the British on the return of Hong Kong in 1984, and the Sino-British Joint Declaration was ratified by both governments in 1985. The following year, the Portuguese reinitiated discussions with the Chinese, and in 1987 the "Joint Declaration on the Question of Macau" was signed in Beijing, setting the date for the return of Macau to full Chinese sovereignty on 20 December 1999. This would be more than two years after the return of Hong Kong, and gave the Portuguese the historical distinction of being not only the first Europeans to establish themselves in Asia, but also the last to leave.
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