He founded the . in Daitōtei, a district in modern-day Taipei, and invited fellow intellectuals to the hospital to discuss contemporary affairs. In 1920 he began participating in the movement to found the Taiwan Assembly. In 1921 he helped found the Taiwan Cultural Association. He was imprisoned for four months in 1923 and again in 1925 for his opposition to the Japanese colonial government. During this time, Chen Tian would lecture in his stead, continuing the promotion of his ideas. In total, Chiang was imprisoned twelve times.