Last month, Chicago’s top cop, Eddie Johnson got into a highly publicized spat with President Trump after he refused to attend the president's speech at the International Association of Chiefs of Police conference hosted by the Windy City. On Wednesday, reports emerged that Johnson may step down amid an investigation into an incident in which officers found him allegedly asleep in his car at a stop sign.
The president went after Johnson from the podium in Chicago last month by saying, "Here's a man that could not bother to show up for a meeting of police chief – most respected people in the country – in his hometown and with the president of the United States. And you know why? It's because he's not doing his job."
Trump also went after Chicago's leaders for embracing an official sanctuary city policy and alleged, "People like Johnson put criminals and illegal aliens before the citizens of Chicago."
Chicago Mayor Lori Lightfoot came to Johnson's defense and dinged the president by tweeting, "It’s no surprise that @realDonaldTrump brought his insulting, ignorant buffoonery to Chicago. Luckily, in this city, we know the truth and we will not let anyone — no matter how high the office — denigrate who we are as a people or our status as a welcoming city."
"When you have a person like President Trump that comes to the city of Chicago for a police conference, I would think that the city officials would take the opportunity not to criticize the president, but to go and say, 'Listen, these are our needs,'" he argued in an interview on Monday.
"But instead," he continued. "People like the mayor of Chicago is putting ego and politics in front of the black bodies that are being buried in the streets of Chicago on a regular and consistent basis."
Caldwell argued that he understands the issues plaguing Chicago better than most because he was born and raised there.
"I grew up extremely poor. Lights, gas, water off at the same time. Mom addicted to drugs," he recalled. "We moved out to a new house seemingly every year because we would either close to being evicted or something of the sort... I've seen the city in decay. I lived it. It's the lived experience. I lived in the projects. So I understand it from an angle that many people don't.
Fox Nation host David Webb suggested that the elected officials in Chicago cannot be relied upon to fix some of these issues on their own.
"This is a problem that [Mayor] Lori Lightfoot has been clear about. She's not going to address it because she believes in [the sanctuary city policy]. So does [Chicago Police superintendent] Eddie Johnson and we can only take them at their word and their actions," said Webb.
"It has become a sanctuary to everyone except for the people that live in Chicago and that's truthfully a sad situation," said Caldwell, recounting the story of his own family. "My grandfather, small business owner, plumbing-construction guy, south side of Chicago, during the 90s, he did very well... until he began to get underbid by contractors who were using illegal help. That's when I began to develop my views on illegal immigration because I saw that it was legitimately hurting individuals within my family."
"It's a really personal dive into a city in which I love so much," said Caldwell. "As a city that gave me everything, I got involved in politics when I was 14-years-old, and I'm really disappointed and disgusted by what has happened to this great American city... We interview gang members. We interviewed teachers, police detectives. I talk about my personal life story and journey coming up in the city of Chicago. And I'm really, really excited that individuals across this country will be able to get a very inside view of the city of Chicago from someone who really loves it."
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Fox News' Greg Norman contributed to this report.