[5] Many of his political allies were notorious and seedy figures such as "Bathhouse" John Coughlin and Michael "Hinky Dink" Kenna,[5] both members of the so-called Gray Wolves.

[5] Harrison's aspirations of power in the Democratic Party came in to conflict with former Governor John Peter Altgeld.

[5] Despite having lost his bid for reelection as governor in November 1896, Altgeld was a prominent national political figure,[6] and had, since early 1896, held fragile control over Illinois' Democratic Party.

[5] Altgeld had been the most prominent Democrat in the state, and had strong advocacy of free silver and an obtained a pro-labor record as during his governorship.

[5] Altgeld also was supported by reformist Chicagoans, such as Clarence S. Darrow, Murray F. Tuley, and Edward Fitzsimmons Dunne.

[5] In March 1898, Harrison's allies, through ward-level victories in Chicago, gained control of the Cook County Democratic Party Central Committee.

[5] Harrison also, soon after, announced that he had negotiated a formal alliance with Tammany Hall leader Richard Corker, much to the preterition of Altgeld's wing of the party.

[5] In response, Altgeld would imply that Harrison was abandoning the cause of free silver (Tammany Hall had notably opposed it during the 1896 election cycle).

[5] In December 1898, after consideration, Altgeld made a widely anticipated announcement that he would challenge Harrison for the mayoralty.

[6] Realizing that he could not win the Democratic nomination, as Harrison had coalesced control of the city party, Altgeld opted to challenge him as a third-party candidate in the general election, backed by the Municipal Ownership League.

[5] With Harrison removed from office, they believed that Altgeld would again be the undisputed leader of the state and local Democratic parties.

[5] Harrison began to, out of what appeared to be desperation, solicit the endorsement and support of individuals such as Timothy Ryan, whose candidacy he had earlier opposed for Cook County Democratic Party Chairman.

[5] Altgeld accused Harrison of turning a blind eye to corruption and abandoning the reformist platforms he had campaigned on in 1897.

[5] Starting in February, Altgeld began delivering public speeches to increasingly large and excited crowds.

[5] Republican nominee Zina B. Carter sought to run a positive campaign focused on returning business values to city government, and largely avoided attacking either Harrison or Altgeld.