Jefferson, who was the nation's third president, owned slaves. Webster was a former senator who supported slavery. Renaming committees were formed for each school, and included people in the community, students and staff.
The school board heard concerns from the public Tuesday night over one of the finalists in the running to be the new name for Thomas Jefferson Middle School.
The country's first Black President and First Lady, Barack and Michelle Obama, is one of the top three choices for the school's new name, but is drawing opposition in the area with a large Latinx population.
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"I will not be part of renaming a school after someone who did not and does not represent the undocumented community," said District 60 school board member Edgar Castellanos. Castellanos said he came to the United States undocumented as a child.
Waukegan activist Julie Contreras works with a group that runs shelters for undocumented children at the U.S./Mexico border.
She said former President Obama failed to deliver on promises to help the immigrant population.
Contreras, who leads United Giving Hope, is organizing protests against naming the school for the Obamas.
"From the time Barack Obama became President until 2017 when he left, he today is still the highest ranking president with deportations in our nation," Contreras said. "We feel that Barack Obama did disservice to us. He denied us, and he didn't stop the deportations, the way he promised."
"I personally don't object to the name, but I have to be aware of the concerns," said school board president Brandon Ewing.
Members of the area's Latinx community held a protest outside the meeting's doors Tuesday night.
"If you're removing the name of Thomas Jefferson - one oppressor - the name of Obama is another oppressor and our families do not want to see that name," Contreras said.
Mauricio Sanchez's father was deported in 2015 under the Obama administration.
"It was something very sad," Sanchez said. "We couldn't even say goodbye to our dad. We just hoped for him to be able to get out."
His dad is still in deportation hearings to this day. The Sanchez family said the Obama name is a reminder of their current struggles.
Others who spoke about the name change endorsed another popular choice to rename the school after: Civil Rights icon John Lewis.
A final decision has not yet been made.