Although the tone of these newspaper articles (and most others as problems progressed) suggests a light-hearted tale, action against Streeter proceeded to the state's courts, as seen in the ongoing legal battle between Streeter and N.K. Fairbank.

An 1889 legislative act (later contested) authorized the Lincoln Park Commissioners to create Lake Shore Drive by claiming and filling lake land. The commissioners sold the open space west of the road to lakeside property owners who agreed to fill the land. One of these landowners, N.K. Fairbank, alledgedly gave Streeter permission to dock on his property and then was unable to convince him to leave. Fairbank won his suit to have Streeter ejected from his property, but the case was overturned on a technicality and Streeter remained in place.