First came the announcement Monday afternoon that Emanuel's primary rival, Chicago Teachers Union President Karen Lewis, will not be running for mayor.
Lewis had yet to formally enter the race, but was seen by most pundits as the challenger with the best shot at defeating Emanuel in the mayoral election Feb. 24.
The fiery union leader was hospitalized on Oct. 5 and it was reported by both the Chicago Sun-Times and Chicago Tribune that she is suffering from a cancerous brain tumor, reports that the Lewis exploratory committee has not confirmed.
Her exit from the race took place the same day that campaign contribution limits in the contest disappeared thanks to an Illinois state law that voids contribution caps should any candidate contribute at least $100,000 to their own campaign within a year of the election. Conservative candidate William J. Kelly topped that amount Monday with a $100,000 donation toward his mayoral campaign.
The Chicago Tribune notes this move will allow supporters of Emanuel, who has already raised over $9 million toward his reelection effort, to contribute beyond what they've already kicked in at or below pre-existing contribution caps.
The remaining mayoral challengers include Ald. Robert Fioretti, community activist Amara Enyia, former alderman Robert Shaw and police officer Frederick Collins. Fioretti, the best-known candidate in the race to date, has so far raised just under $400,000, according to the Tribune.
Dick Simpson, a University of Illinois-Chicago political science professor and former alderman, told HuffPost that he expects the campaign contribution limit change will benefit both Emanuel and Fioretti, though the incumbent mayor will likely get a bigger boost via more of the large-sum, out-of-state contributions he received during his 2011 campaign.
Another high-profile rival of the mayor's, Cook County Board President Toni Preckwinkle, already announced in July she would not be running for mayor.
The filing deadline for Chicago's mayoral race is Nov. 24, giving leeway for additional candidates to submit petitions but little time to lay the groundwork needed for such a major campaign, Simpson said. He expects Fioretti to remain the highest-profile challenger to Emanuel in the 2015 race.
"You can't decide today to run for mayor and be a credible candidate," Simpson said.