Actually, there was no free press under Chiang. He found that to be annoyingly counterproductive to maintaining his dictatorship over China. Whoever acted like a free press,l he'd get his fascist organization the Blue Shirts to assasinate them. He even outlawed reporting of the KMT-c aused 2-28 Massacre, under penalty of death. Martial law existed in Taiwan from 1949 until 1989, and essentially whatever reversals made were b/c of the courageous waishengren and benshengren who fought the system.
Frank Dikötter says it better than I could:
(emphasis mine)
The Age of Openness: China Before Mao said:It goes without saying that politically offensive publications could be closed down and journalists were arrested and executed, although the degree of government interference varied hugely during the republican era. Under the early republic, for instance, many new publications flourished thanks to the decentralisation of power, while publishers in Xi’an were free to criticise Chiang Kai-shek even at the height of censorship under a unified Nationalist party in 1936, thanks to the patronage of two powerful governors. Stephen MacKinnon is right to point out that freedom of expression during the republican era was limited, but one wonders in which countries between the two world wars the press was entirely free from political influence.^52 In contrast to countries such as Germany and Russia, a large number of publications in China in the 1930s were relatively open thanks to a politically diverse situation in which editors and writers could always find either foreign protection or political patronage, from foreign concessions in Shanghai to cities controlled by regional governors critical of the central government. The Dagongbao, China’s most important newspaper before 1949, published commentaries which often lambasted Chiang Kai-shek, and advocated press freedom and political opposition.^53 Edgar Snow could not only visit Mao Zedong in Yan’an, but his propaganda piece in favour of the Communist Party was translated and distributed in most parts of the country. Even with censorship, often erratic and inconsistent, the opportunities for political expression outside of the ruling party before 1949 by far exceeded anything even remotely possible under emperor or Mao.
The relative freedom enjoyed by the press, as well as the even greater freedom of religious belief and personal movement (no hukou system back then) come from the fact that the KMT was not a totalitarian-minded system, even if it was authoritarian. It was demonstratively open to reforms and improvements, and did not see Tiananmen-style repressions as the norm. Yes, the 228 massacre was horrible, but how often did it happen, and under what desperate circumstance?
Were it not for the relatively open and corrective nature of the KMT, the Taiwanese dissidents who campaigned for democracy would long be either vaporized, in labor camps, or transformed after long sessions of "thought work." Suffice to say Taiwan would not be a democracy either and the benshengren would have had their identity erased completely.
EDIT: I'm not trying to say that Chiang Kai-shek was some enlightened dictator or that he was correct to be corrupt. It's more that in criticizing him and his government one has to look at the context, and in his particular context he wasn't worse than the other viable players of his time. Otherwise the discussion just devolves into emotional reactions to isolated details, and loses rationality.
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