Entry in progress—B.P.

22 March 1892, The Daily Inter Ocean (Chicago, IL), pg. 7:
“I WILL.”
This Chicago Expression is Disturbing the Brethren of the Hub and New York.
Boston : THE INTER OCEAN has awarded Charles Holloway of that city a prize of $200 for a typical figure of the occidental metropolis. Mr. Holloway’s sketch is that of a female of heroic pose with a crown of flames and emblems suggesting the Phoenix. On her breast is a cuirass bearing the words “I will.”

“I will”—what?

“I will” hornswoggle Congress or “I will” keep my promise to pay the cost of constructing and opening the World’s Fair. I will pause for reply.

Chicago (IL) Tribune
City Spurns Its Old Symbols
Has `I Will’ Become `i Want?’
November 09, 1999|By Doug Bukowski. Special to the Tribune.
(...)
It was a fair, represented by one of those stars on the flag, that prompted the creation of no less than three of our city symbols. In 1892, the approaching Columbian Exposition spurred the Chicago Inter-Ocean to sponsor a contest for the best image “typical of (Chicago’s) spirit,” as one of the newspaper’s editors put it. So was born the “I Will” woman.

“I Will”—Chicago’s longtime motto, which contrasts with the millennium celebration’s frothy slogan, “For the time of your life”—was meant as a testament to civic gumption and perseverance.

Both woman and motto were the product of contest winner Charles Holloway, a prominent Chicago artist. Holloway created a figure that was a mix of Helen of Troy and Dame Liberty, with a helping of Chicago attitude. She wore a breastplate adorned with the phrase “I Will.”