The power of incumbency not only helps the mayor raise his own money, but it also tends to discourage wealthy business owners from contributing to other candidates because of potential backlash.
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But Rocky Wirtz bucked that trend with a large donation to Paul Vallas. Wirtz gave the Vallas campaign a total of $200,000 through five companies he owns.
"I think the Rocky Wirtz contribution to Paul Vallas kinda awakens the business community that if he can do it, maybe I can," said political strategist Thom Serafin. "Historically, here in the city of Chicago, it's always been intimidating to break out and give money to someone who's opposing the incumbent mayor."
Willie Wilson's $100,000 donation to his own campaign lifted fundraising limits in April. That move opened the door for Emanuel to tap into big donors.
"There have been 23 contributions of $100,000 or more since the loophole," said Executive Director of Illinois Campaign for Political Reform Mary Miro.
Miro said these large donations raise concerns about what influence the average Chicagoan can have in the mayor's race.
Emanuel's campaign fund is currently $8 million and far outpaces his nearest rival, Lori Lightfoot. Lightfoot reports $500,000 in campaign contributions since her campaign began 50 days ago.
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Garry McCarthy reported a $50,000 donation from his campaign chairman, Brian McCormack, Tuesday.
Dorothy Brown has reported $36,000 in campaign fundraising. Her quarterly report filed Monday lists just $2,500 on hand.
Willie Wilson loaned his campaign $90,000 last week after his $50,000 donation in June.
According to Serafin, Emanuel is sending a message with his early campaign stockpile.
"Well, he's telling everybody, 'No matter who you are, where you come from, and what you think, I am going to be there ahead of you, in front of you, behind you, and around you and before you know what's happening I will have created the narrative,'" Serafin said.
Emanuel declined to comment on the race at a Pianos in the Park event Tuesday.