[5] By 1903, an anti-Harrison coalition had begun to arise in Chicago, consisting of members of union ( including in the Chicago Federation of Labor), former Harrison ally Robert "Bobby" Burke's followers, and remnants of what had been the once-strong Altgeld wing of the Democratic party.

[5] The convention, however, was noted as having been a rather unenthusiastic affair, appearing to signal more tepid or reluctant support of Harrison by his party.

[8] With an exceptional reputation for honesty and public service, Stewart had long been considered a potential candidate for mayor of Chicago.

[5][12] Beginning at the start of 1903, there had been a strong push among members of the Chicago Federation of Labor and others to draft Darrow as an independent candidate for mayor.

[5] After an active and organized effort to draft him, which even included a nominating convention-style pro-Darrow mass meeting held at the Auditorium Theatre on February 16, and active consideration of a prospective run on his part, it appeared in late February that Darrow might be preparing to enter the race.

[13] Stewart advocated making immediate improvements to its conditions by accepting the best terms the streetcar companies were willing to offer.

[13] Harrison worked to paint Stewart as a puppet of corporations and special interests, particularly the streetcar companies.

[5] They also worked to paint him as having made few substantive accomplishments in his tenure as mayor, and utilized the slogan "six years, nothing doing" against Harrison.

[5] In the coinciding Chicago City Council election, Republicans won a weakened majority.

[13] Stewart had overwhelmingly won the vote in first precinct of the twenty-first ward, where both he and Harrison resided.