Wilson visited a senior home on Chicago's South Side last Friday, creating excitement with residents with a cash giveaway.
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"People who answer it, maybe a couple people, we're gonna give them $100," Wilson said.
But this is also generating concern on the campaign trail.
"Well, you're running for mayor of the city of Chicago, you're passing out money to our older individuals in their senior homes and with campaign literature," mayoral candidate Roderick Sawyer said. "If you add it up, it's totally unethical."
Wilson also posted on his campaign's Facebook page another cash giveaway, one of five similar stops he made that same day.
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Wilson is defending his philanthropy as something he's done for years.
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"We always done that," Wilson said. "I'd rather lose the election versus see somebody starving to death."
In fact, Wilson came under scrutiny in 2018 for giving out cash at a church where he campaigned with Governor Bruce Rauner. The State Board of Elections investigated, but cleared Wilson of any wrongdoing.
Mayor Lori Lightfoot's campaign called Wilson's recent cash handouts "seriously concerning," adding: "We all need to protect the integrity of the vote - even the appearance of vote buying must be taken seriously by the Board of Elections."
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Wilson denies he was trying to buy votes.
"I don't have to do that. I wouldn't do that. It wouldn't be fair of me. I don't take advantage of anybody," Wilson said.
But as Jesus "Chuy" Garcia launches his first TV ad in this campaign, hitting the airwaves Wednesday, he also is raising concerns about Wilson's campaign.
"He may have good intentions, but there are campaign ethics and there are laws an effort to buy votes," Garcia said.
Wilson says regardless of the scrutiny or the optics of his cash giveaways, he will continue to help people in need, saying that is more important than winning an election.