Chiang's police record in the British-administered International Settlement grew over the years to include murder, extortion, numerous armed robberies, and assorted other crimes. He was indicted on all the listed charges, but was never brought to trial, or jailed.
[Chiang Kai-shek] abandoned himself to a life of intense dissipation. He would disappear for months from headquarters in the houses of sing-song girls, and for some reason or other he acquired a fiery, uncompromising temper which weighed very tryingly on his friends...He also came into contact with the leaders of the secret societies of Shanghai, which later on became very useful to him in his dealing with the Shanghai capitalists.
In an act of calculated treachery, Chiang ordered his army vanguard to stop 25 miles outside Shanghai. Some of the headless bodies that littered the streets of the city clutched handbills that read: 'WELCOME CHIANG KAI-SHEK, GALLANT COMMANDER OF THE CANTONESE.'
But Chiang Kai-shek had other ideas. He had to replenish his army' bankroll. Shanghai's financiers had regarded him as their savior. Now they discovered to their everlasting dismay that he was to be their tormentor. The White Terror was turned against the wealthy merchants. According to journalist Sokolsky, 'Every form of persecution was resorted to on the pretext of hunting Communists. Men were kidnapped and forced to make heavy contribution to the military fund..
Next, Chiang issued his own short-term 'government' bonds, and used soldiers and Green Gang toughs to force everyone from small shopkeepers to bank presidents to buy them. When one millionaire refused, his son was kidnapped. Another youth, the son of a dye merchant, was arrested as a 'counterrevolutionary,' but released when his father 'donated' $200,000 to Chiang.