He Grew Up Poor in Chicago. Then Conservative Values Helped Transform His Life.

Katrina Trinko /

“After I began to volunteer with this alderman and learn the ways of the Democratic Party … I began to question some of the narratives,” says Gianno Caldwell. “Why is it that although these politicians come every year during election time, why is it the conditions and the communities never get better?” 

That was the beginning of his journey to the right. Learn the full story by reading his lightly edited interview, posted below, or listen on the podcast:

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Kate Trinko: We’re at President’s Club, The Heritage Foundation’s annual meeting, and I’m joined by Gianno Caldwell, a political strategist, a Fox News political analyst, and the author of the new book “Taken for Granted: How Conservatism Can Win Back the Americans That Liberalism Failed.” Gianno, thanks for joining me.

Gianno Caldwell: No, thank you for having me.

Trinko: OK. So you’ve recently tweeted, “Conservative values helped me—a kid from the South Side of Chicago—find a life of opportunity.”

Caldwell: Absolutely.

Trinko: Tell me about that.

Caldwell: So, to know what that means, you have to know a little bit about my story. I grew up on the South Side of Chicago, extremely poor, lights, gas and water off at the same time. Mom addicted to crack cocaine. Grandmother who at one time was a private duty nurse when she gave over temporary custody of me and my siblings, ended up having a car accident, injuring her back and things were really, really bad. What ended up happening—

Trinko: And was your dad in the picture at all?

Caldwell: My dad, I saw him on the weekends and that’s what I was about to go into. My dad, I was blessed to see him on the weekends, most weekends, and he would take me to his father’s house—which was my grandfather—and small business, plumbing, construction, that kind of thing. And he would take me with him on Saturdays to go work with them. He’ll pay me $10 a day to hold the flashlight, hand them tools, and I felt extremely blessed to be able to earn something for myself. And from there … there was a moment really that transcended my life.

One day I was about 14 years old and we’re riding through this area in Chicago called Englewood, it’s one of the hardest hit areas or the hardest hit area in Chicago in terms of the guns, the violence, drugs, prostitution, etc.

And as we were riding, I see this lady who looks beat down, drugged up. She was clearly someone who was addicted to drugs. And I saw my mom and as we were riding, I’m tearing up, my grandfather sees me tear up and he says in this very Southern voice, “What’s wrong with you, boy?” And by that time we were passing this lady and I realized it wasn’t my mother, but it could have been.

And I said, “This lady, what can I do to prevent this from happening?” When he said, what’s wrong with me. He tells me about the elected officials, the power that they have to change people’s lives. … It creates different penalties for those who sell and distribute drugs—the power that they have to provide grant funding for those who want to be rehabilitated from drug use.

And I said, “I want to be an elected official.” So that very next week, at 14, I started volunteering for my local alderman at that time. And I was there every day after school, like it was a job. And that’s what created this trajectory of politics and certainly public service.

So when we talk about conservatism and how I got there, that’s a longer version of the story. But I’ll tell you, what ended up happening is after I began to volunteer with this alderman and learn the ways of the Democratic Party, and I began to question some of the narratives, “Why is it that although these politicians come every year during election time, why is it the conditions and the communities never get better?”

And they will try to shut me down and blame white people for it. Like, “Oh, we’re in Chicago, the white politician, they just give them money to the white neighborhoods.” “OK, well, the politicians here are black. Why is … nothing changing and they’re coming with the same rhetoric year after year?”

So at that point I began to really think really deeply about the differences between both parties. And after having a conversation with a Democrat, a senior Democrat on the street—he’s the alderman who challenged some of my viewpoints on the Republican Party—I went and researched the distinctions between Democrats and Republicans. And I learned that the Republican Party was started in 1854 in opposition to the Kansas-Nebraska Act, which went to expand slavery into the West.

I’m like, “Wow, this doesn’t sound right. This isn’t a Republican Party that people have talked about in my community. The ones that they’ve said were racist and slave owners and pushed Jim Crow and all these other different policies,” which wasn’t true. It was all lies. Democrats were the ones that were pushing those particular policies.

And as I began to further examine, it just seemed like propaganda. Because why is it that I haven’t heard this before and why is it Republicans aren’t talking about this? And after really examining that and realizing that it was all true, [that the] Republican Party pushed every civil rights bill pretty much that there was … even the 1964 Civil Rights Act. I get Lyndon B. Johnson was a part of that, but if it wasn’t for Republicans in the Senate, it wouldn’t have passed, and mind you, Democrats had the majority, they didn’t want to pass it.

So learning these things and understanding the morals and values of conservatism—I come from a line of ministers in my family—learning that the party was anti-regulation. My grandfather, a small business owner often talked about how regulation would drive his business out of business. Immigration policy—my grandfather lost a lot of business deals due to illegal immigration.

I began to see the virtues of the conservative movement as a part of me and that ended up itself was a longer story reconciling what that meant, especially considering what people in my community had said about the conservative movement or the Republican Party for years.

Trinko: Great. And I find that so interesting because I grew up in a different background from yours, where family and friends tend to be very conservative and I always find it very interesting when people are able to convert, as it were. And were you upset when you started to think, “I might agree more with conservative ideas”? And what was the response of your community?

Caldwell: You are asking excellent questions, by the way. Was I upset? I felt sad and depressed, to be honest.

Trinko: Yeah, that’s hard.

Caldwell: Because, you got to keep in mind that Democrats have been really marketing geniuses, it’s painting a picture of the Republican Party and the conservative movement that doesn’t exist. It’s not backed by any factual basis. It’s really emotional rhetoric that’s driven or derived by way of pointing to racism and slavery. That’s really the angle in which they choose to push their messaging.

So what ends up happening is you get a whole community of people who believe this rhetoric and everyone just begins to believe the same. Nothing changes, there’s no one with an individual thought.

That’s why when you look at now the number of African Americans that vote for the Democratic Party [it’s] about over 90%. … And it’s not like their policies are making our lives better. Their policies are looking to entrap us into not just a victimhood mentality, but keep us dependent on government, and that’s troubling. It’s really troubling.

So yeah, I felt sad. I felt depressed. I said, “How could I be one of them?” And it was a long time of soul-searching before I really was able to reconcile what the truth was, how this aligned with me. And when I came out and told folks in my family, they disowned me. I lost a lot of friends. There were women who chose not to date me because of my political affiliations. Things were bad in that sense. And the worst of all, there was not really any conservatives around me … So what group am I going to really go to?

Trinko: Sounds like a rough time.

Caldwell: Yeah, it was rough. It was rough, but it led to a life of opportunity. It really did.

Trinko: In your book, you’re talking about the conservative ideas and the conservative solution. So for neighborhoods like the one you grew up in and inner city neighborhoods, what are the conservative ideas that you think will help them?

Caldwell: Entrepreneurship is a conservative idea that will help people. I think so often, especially considering the dependency the Democrats have empowered themselves with, saying, “Hey, if we can just give you another check, you don’t have to work. Just let me give you another check.” Or if you see in today’s policies, you see counties and cities saying, “Let’s give you a universal income, $1,000 a month so you don’t have to do anything.” That’s a trap. It really is.

Trinko: It sounds a little bit great. No—

Gianno Caldwell: It sounds a little bit … no—

Trinko: … just kidding.

Caldwell: … it really is a trap.

So let’s think about, for example, the ’94 crime bill was something that was pushed by both Clintons—just follow me. [The] ’94 crime bill was something that was pushed by both Clintons and within this ’94 crime bill, if you were an individual who had went to jail for something like having a bag of marijuana, you could not go into public housing. You couldn’t have that person go and live in your public housing, which left women, a lot of African American women, without a man in the home, which brings about those traditional family values.

This left them trapped and dependent on government, because you don’t have anybody that can earn. So what else are you going to do? You’re going to stay in this same cycle.

If we think about the fact that if you received these particular benefits and you say, “OK, I want to come out of this cycle and I want to go get a job,” maybe you don’t have skills, maybe you don’t have education. So what kind of jobs are you willing to get? A minimum wage job.

“Well, I’m going to go and get this job and I’m going to try.” Well, maybe on your first, second, third check, you’re getting a letter from the state government or whomever saying, “You’re making a little bit too much money. We may have to cut you off from your benefits.” What does that do? “Well, if you’re going to cut me off on my benefits and I’m not making much money, I’m just going to stay collecting your checks.” That’s a trap. Are you following me?

Trinko: Yeah.

Caldwell: So, how do we break through? We reform the system. Legitimately you reform the system and you bring about individuals within the community. It can really be a testament to a change in the dynamic.

Trinko: So how can conservatives communicate this message? Because you just told me half the people in your life rejected you when you became a conservative, even after knowing you for years and years and hopefully, eventually, some of those relationships healed. But, conservatives walk into an African American community and it’s like … there’s no credibility. So how do conservatives reach African Americans?

Caldwell: This is like a very interesting thing that I’m about to say. And truthfully speaking, in 2016 when President Trump ran—I have always been a defender of the president where I believed appropriate. That’s the key word—because I don’t defend everything—when I believe appropriate.

And President Trump was one of the smartest messengers that the party has ever had. He went in and said, “Listen, your schools are broken. You can walk down the street in Chicago and get shot. Unemployment is bad. They’ve taken your votes for granted.” This is what he said to the African American community. Unlike some Republicans that may say it one time, he continued to say it.

But it wasn’t just him saying it, we got a list of deliverables from this president: the lowest African American unemployment rate in history, deregulation of the economy, more people to work than we’ve ever seen ever, a change in the immigration dynamic, where we know a lot of African Americans are disenfranchised by illegal immigration, including my grandfather.

Who’s the messenger? We need messengers that are forceful like President Trump. We’re going to speak the facts and we’re going to communicate them continuously. And by virtue of the results through the Trump administration, we have credibility, and that’s really it.

And I know it’s a tough pill to swallow for a lot of people, but you definitely don’t want to go and speak in a way that may not be appropriate, but certainly you definitely want to communicate the results that have been done by where this administration, and Republicans usually run away from that kind of thing.

Trinko: So do you think overall the African American community thinks well of Trump and thinks of his results or do you think the message is not getting out or what’s actually going on in the ground here?

Caldwell: OK, so let me take you back because I can tell you something by using the factual data, the reference.

So during the 2016 election, you had about every influential African American on television saying, “Don’t vote for Trump, etc.” Then we see his rhetoric, him continuing to mention policies that impact the black community, what he’s looking to do for the black community.

Again, something we had not seen from, and let me be clear, a Republican president in that … way, because a lot of Republicans are very concerned about being considered racist or being called racist … [for mentioning] just the simple facts about the unemployment rate in the black community or how some of these communities have really and truly marginalized. “Look at Baltimore, look at Chicago, look at … ” Then people will say, “Oh, you must be racist because you’re mentioning these things.” No.

So when considering that, he continued to do it. The data show that he won more African Americans than Mitt Romney and John McCain. He was double digits for African American men at 12% and he was about 8% for African Americans overall. He was over in the 30 percentile for Latinos because he kept on message. He continued to communicate that, and I think that’s important and powerful.

Trinko: OK. … So to switch gears a little bit, you grew up in the inner city and I think one of the things that the left talks about a lot these days that there’s a lot of concern about is, is the American dream still alive for all Americans and is it possible? You had your dad in your life, it sounds like it’s a really positive influence—

Caldwell: My grandfather especially.

Trinko: … and your grandfather, but for other kids who may not have any father figure, is the American dream still alive for them?

Caldwell: I would say, yes. And let me be very clear. There’s a total of nine of us, my siblings and I. There’s seven different dads of these nine kids, and what? It was maybe my dad was active. He was the most active of them all. … Yeah, one of them would send gifts on Christmas, that kind of thing, maybe a birthday. And I can tell you, some of my siblings aren’t doing well, but then there’s others that are doing very well. They may not be doing the kinds of things that I’m doing, but they needed examples of what was possible.

That’s why I push in my book, “Taken for Granted: How Conservatism Can Win Back the Americans That Liberalism Failed,” the power of mentorship.

… There’s [a group] called 100 Black Men of America, and these guys, their philosophy is, “Kids will be what they see.”

So you got all these successful African Americans who went out and they’re business owners, they’re politicians, they’re lawyers, they’re doctors, and their focus is on giving back to communities that they may have come from. And I think that’s important to do, whether you be black, white, or whatever.

If you’re listening to this and you feel like you can fill a void of mentoring people, not just black kids, because my book, although my story is where I come from, I’m black, but there’s kids in the Appalachian region, they can benefit. Those are people who have been told that the American dream is dead. They’re experiencing similar problems as I did growing up. The difference between me and them is the color of our skin, but it’s just as bad [for] them.

And I think, that’s really for me, that’s the focus. The American dream is for everyone and it’s available for everyone. But the liberals have really made it a punchline, like, “Oh, unless the government is really helping you, you can’t make it.” And that’s a lie.

Trinko: Okay. Now, you mentioned all the good things that President Trump has done for the black community, but a clip of you talking about Charlottesville two years ago went viral and you were crying and very upset. … Do you think that’s still affecting how blacks perceive the president? And do you think there’s other areas where maybe the President could grow in his outreach to African Americans?

Caldwell: Let me be very clear, and I talk about Charlottesville in this book, this president, as I told you, in 2016, I defended him where I believed appropriate and I lost even more friends and family over that. I believed in his messaging on a number of issues.

And yes, I also talk about in my book, “Taken for Granted,” about holding members of your party accountable, even more so than even the other side. Because in that moment we needed a president that was going to unite us and not divide us, and his language to me was divisive, and there was a number of members of the Republican Party who support him, senators, Congressman, etc., who also said that it was dividing language. So I wasn’t alone on that front.

And it really impacted me, because I happen to work for the No. 1 cable news network in the country. People actually listen to what I say and I was hired for a reason and certainly to express how I felt in that moment coming from where I come from with something that the president needed to hear, and the White House did hear me. They heard me loud and clear and they let me know about an hour or two after that segment began to go viral what they thought about it.

And a matter of fact, even to be even more clear, and I talk about it in a book, before that segment even aired, I was in touch with the White House, saying that President Trump needed to get in front of the cameras and we needed to have a dialogue on race in America.

Think about what happened in 2001, I know it’s different, but when we were attacked in 9/11, we needed somebody that was going to bring us together, and that’s what George Bush did. It didn’t matter if you are a black life, black or white, we were brothers and sisters, we were Americans. And that was an opportunity I think that the president certainly missed, certainly.

Trinko: OK. So lastly, you write very movingly in your book about your mom’s drug addiction, and that’s a problem that we see more and more, the opioid addiction. But even here in D.C., there are certain places, Union Station, a corner of New York Avenue, where I regularly see people who seem to be on drugs and addicted, and it’s heartbreaking, and it seems like a problem that no one is able to solve. What do you think we both as communities and as policymakers should be doing?

Caldwell: And I’m going to have to go to this point again: President Trump in 2016, he talked about this crisis and he said he was going to do something about it. Him, with him, his administration, and Congress, they passed the bill and they provided a lot of money, hundreds of millions of dollars I believe it was, to this fight and it’s been working out.

There’s been a reduction in deaths for opioids and there’s also been a change in dynamic on how people view it. There’s been more education, there’s a more serious consideration around it versus some kids that are just popping pills here and there. So people are taking this matter very seriously. So that’s something that we can thank the administration for.

For me, it was a lot different when I was growing up. Crack was something that impacted mostly black communities. There was a lot of people who said, “Lock them up.” There wasn’t a lot of compassion for those who were on those drugs.

And you see the continuation of that through the ’94 crime bill. People were demonized and that’s why I’m so big on that, because they really created a mass incarceration generation, the Clintons and the Democratic Party. Republicans didn’t support that bill. There were a few Republicans that supported it, but the majority of Republicans didn’t support it.

So having these discussions and putting politics aside, I think we’re going in the right direction on it. And so long as more people are informed about the ability to get help and be rehabbed from this addiction, which is very serious and impacts millions of families, I think that’s really the route to go in terms of changing the dynamic in our country. And I see it going on every day. I see a change. I really do.

Trinko: OK. Gianno Caldwell, he’s the author of the new book-

Caldwell: Wait, wait. Don’t jump out yet. I mean, we’re talking a little bit more, am I right?

Trinko: Well—

Caldwell: I get it. It has been endorsed by Ann Coulter, Brian Kilmeade, of course, Mrs. [Kay Coles] James, the president of The Heritage [Foundation], Ben Shapiro, Newt Gingrich, and Clarence Cox III. I thank you so much for your time, and please have everyone now follow me on social media, @GiannoCaldwell.

Trinko: OK. Thank you so much.

Caldwell: Thank you.

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