Obama hopes to swing the same vote of confidence for Harris that Black men had in him during his term.
A New York Times poll shows 78% of Black voters say they will vote for Harris, which is significantly lower than the 90% Democrats have pulled in past elections.
"I'm speaking to men directly," Obama said at his campaign event. "You're coming up with all kinds of reasons and excuses... It makes me think that, well, you just aren't feeling the idea of having a woman as president."
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At Leo High School, students debated in their morning journalism class that one of the reasons Black men may not support Harris is her history as an attorney.
"She did prosecute a lot of Black men," said TyShaun Glenn, student.
"I think a lot of people go, OK, she's putting our brothers and sisters in jail," said first time voter Kaleb Larry. "Even though she is trying to go for affordable housing, healthcare, a lot of the expectations of Black communities."
The high schoolers, some of whom will be first time voters, say some men are having trouble trusting a woman as president.
"That's like, that' just basically an excuse to me, like, you don't want to vote," said first time voter Derrion Anderson.
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And they say she should take the direct approach to overcome that hesitance.
"She just got to take the risk and, like, talk to Black men," Glenn said.
Former CPS teacher and education expert Ernest Crimm III said he doesn't want young Black men to overlook the support the vice president does have.
"Kamala announced that she was running, you have all these black men getting on the call to raise all of this money, and that seems to be a complete afterthought," he said.
But these students emphasized they care less for the online arguments, and think the heat is social media-driven.
"The comments, people trying to call out and generate a little bit of outrage," said student Kamren Cato.
They care more for the policies a candidate brings to the table.
"We don't have time for misogynistic views or preconceived bias," said Larry. "We need to focus on the policies that aid us as American people."