Apparently the Bull Moose impersonator hangs out on the most distant edge of town, where the towers of the city are visible only in the distance:

A little history:

The Two-Mile Crib was constructed as part of a scheme by Ellis S. Chesbrough in 1865, to help with the purification of the water because of damage caused by the city dumping sewage into the lake. Construction of the crib began in May 1864, miners and workers worked 24 hours a day and six days a week. The total completion of the project was in March 1867 and cost the city $380,784.[8] Purified water was pumped to the Chicago Avenue Pumping Station which still stands to this day on North Michigan Avenue.

I guess people were expected to know what a water crib was.

The Municipal Pier - which you know as Navy Pier - opened July 15, 1916. This cartoon ran on June 8. SCOOP COULD SEE THE FUTURE