How and why did the "Green Gang" hold the balance of power in Shanghai in 1927?

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For what I remember, Chiang's relationship with the Green Gang is addressed in detail in Sterling Seagrave's The Soong Dynasty ("One loved power, one loved money, one loved China: three remarkable sisters who shaped China's greatness") and to a lesser extent also in Jay Taylor's The Generalissimo: Chiang Kai-shek and the Struggle for Modern China. Here's from the introduction of a Seagrave's 1985 account:

Chiang's direct connection with the notorious Shanghai Green Gang after the winter of 1926-27 has been known for many years, but there has been only a vague understanding that those links went back much earlier, and of how they affected this career. It is now possible for the first time to see the "Divine Skein" linking them all the way back to his youth, before 1910, and the manner in which the Green Gang leaders used Chiang decisively (and were used by him) to snatch the revolution from the hands of Dr. Sun Yat-sen's coalition. Things that have only been rumoured can now be seen rather starkly, and Chiang's takeover, which never made much sense in the official version, begins to make sense now for the first time.

Unfortunately at present I cannot remember how events unfolded in this book's account, so I'd rather direct you to it rather than revisiting it myself all-too-quickly.

BTW, I do remember repeating fun occurrences of Chiang's dentures in Taylor's biography of the great man :)

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The Green Gang were among Chaing Kai-shek's largest financial backers - they saw the communists as bad for business, and the Nationalist forces welcomed the money and street-level intel the triad could provide. Kai-skek needed the Green Gang to retain his hold on the KMT over challenges from Jingwei, and bring the left wing of the party to heel.

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I am writing this answer as the son of two Chinese immigrants to the U.S. My father happens to be a nephew of this man: http://en.wikipedia.org/wiki/Liang_Shiyi. Elder members of my mother's family were also involved in Chinese politics. As my mother would say, "Chiang Kaishek did not have a very big chest" [heart]

Chiang Kaishek was a military man who didn't have many friends outside the military, with the notable exception of this man What family or other connection bound Chiang Kaishek and Cai Yuanpei, two ideological opposites? As "gangsters" the Green Gang was "paramilitary," which meant that Chiang Kaishek was more comfortable with them than with non-military people. Chiang, in fact, formed a friendship with Du Yue Sheng during his stay in Shanghai from 1915-23.

Chiang's army could handle a few thousand Communists by itself, no problem. The issue was that Chiang was also against the labor unions, whose members numbered in the hundreds of thousands. In this particular fight, he didn't even have the full support of his own (Nationalist) party. So he had to user "outsiders" who happened to be his personal friends.

The Green Gang provided more than just "guns." They were "locals" to Shanghai, which means that they could find political opponents more easily than Chiang's army. Also, they did a lot of "dirty," extralegal work.

According to this link http://en.wikipedia.org/wiki/Shanghai_massacre_of_1927 some two or three hundred Communists (representing about 1% of a Communist party numbering in the tens of thousands) were arrested, and executed with great fanfare. But there were 5,000 "missing," mostly labor unionists, representing about 1% of the union members. Most of these died "accidentally on purpose' ("jumped" out of a tall building, "fell" into the river, suffocated and entombed in some cellar, etc.) Interestingly, top level Communists like Chen Duxiu and Zhou Enlai were not killed, because Chiang's strategy was spare the generals and slaugther the captains (the 1% below the very top).

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