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Paul Wyatt Caraway was the third High Commissioner of the United States Civil Administration of the Ryukyu Islands (USCAR) from February 1961 to July 1964. He is regarded as a figure who exercised considerable influence as High Commissioner and is known to have delivered a speech “autonomy is a myth.” Meanwhile, it is a lesser-known fact that the American jury system was introduced in Okinawa around the same time. Furthermore, the extent of Caraway’s involvement in the introduction of this system has not been adequately addressed in previous research. This paper does not address the evaluation of the speech, however, the fact that Caraway’s distress regarding the implementation of the jury system was the underlying factor in this severe rhetoric offers a novel perspective on the speech. This paper elucidates the jury system, which could be regarded as a form of self-government within the judicial framework, was established in Okinawa mere three days after his speech (March 8, 1963), as well as Caraway’s contradictory contribution. This research examines the Ikeda case, which was a trigger incident in the establishment of the jury system in Okinawa, and provides a comprehensive examination of the circumstances surrounding the introduction of the jury system and the correspondence between the Army authorities in Washington D.C. and High Commissioner Caraway. Consequently, it becomes evident that Caraway himself was the individual who, ironically, played a pivotal role in the establishment of the progressive jury system.