As a newly elected delegate from Hawaii, Wilcox proved to be fairly ineffective. On the floor of the United States House of Representatives, Wilcox was challenged by his poor command of the English language, and his lack of alignment with either of the main parties (Democrat and Republican). Although upon his election, he took a more moderate tone, the Home Rule Party proved to be obstructionist and was blamed for a distinct lack of progress in the Territorial legislature. One particular political miscalculation of note was Wilcox's support of the so-called leper bill, which cost him a great deal of support amongst his native Hawaiian base.