That summer, N.K. Fairbank, who claimed rights to the area, arrived to inform Streeter he was an illegal squatter and would have to leave. Street chased Fairbank off with a shotgun. Shortly thereafter, Streeter chased away the constables who had come to evict him. Further attempts to remove them were met with gunfire and scalding hot water. After one such raid resulted in an arrest for assault with a deadly weapon, Streeter was acquitted on the grounds that buckshot was not considered deadly.
Although Fairbank sued Streeter in 1890 and won, Streeter maintained his hold on the District, which was now home to prostitutes, transients and other "undesirables." During the World Columbian Exposition, Streeter refloated the Reutan and used it to ferry passengers to Jackson Park and Streeterville.
From 1894 on, there were many attempts to forcibly remove Streeter from the District. In cases in which police were injured by axe and gunfire, Streeter and his men were invariably found not guilty due to acting in self-defence. Streeter's fight for what he considered his land continued until his death on January 24, 1921, although he and his second wife left Streeterville to move to East Chicago, Indiana in 1918.
The site of Streeter's shanty is currently occupied by the John Hancock building.