A Fox News political analyst tackles some of our communities’ toughest challenges with timely insight from his own life: the story of how conservative values helped a kid from the South Side of Chicago find a life of opportunity.
“A must-read.”—Brian Kilmeade, bestselling author of Sam Houston and the Alamo Avengers
Born to a mother consumed by drugs and raised by his grandmother in poverty on the South Side of Chicago, Gianno Caldwell saw firsthand how lawmakers from both parties have failed African American voters on issues like poverty, welfare, and education. But as someone who beat the odds growing up under a fear-based mentality that limits what people can achieve, Caldwell believes there’s another way.
In this groundbreaking book, the Fox News analyst describes his personal journey while detailing a hopeful vision for a nation no longer beholden to identity politics and self-limitations. Trapped within the expectations and traditions of our communities, families, political parties, faith, race, and gender, we fail to challenge our politicians and ourselves to create real change. Now more than ever, we need to confront preconceived notions about the Democrats and Republicans, public policy, and American history.
Looking at the obstacles facing urban communities, such as crime, education, and social mobility, Caldwell digs beneath the statistics. By spotlighting the moments that enabled his rise to success, he proffers steps that can help more people overcome the odds—whether through policy reform or the heroic efforts of men and women who are already working to make a difference in their own communities.
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Gianno Caldwell is a Fox News political analyst and the founder of a bipartisan consulting firm based in Washington, D.C., that provides strategic advice in the areas of public affairs and government relations. For seventeen years, Caldwell has held roles at the federal, state, and local levels of government.
Chapter 1
A Spy for Obama
My Introduction to the GOP
Not long ago, I walked up to a well-known black actress to introduce myself, someone you’d know from the movies she’s starred in. As I extended my hand, she shot back a damning look of revulsion. “I know who you are,” she said. “You’re that Republican from Fox News.” It was the end of that conversation.
Another time, at a Hollywood party, I was having a great chat with another popular actress and comedian. Just as we were about to exchange contact information, it became clear I was a Republican, and the conversation ended abruptly, without another word, as she turned and walked away. I stood there alone for a long time, like a kid stuck against the wall at an eighth-grade dance.
A couple years ago, on a blind date, the two of us got around to discussing our work. “Oh my God!” my new friend gasped, as if she’d just discovered she was sitting in the car with Jack the Ripper. “You work for Fox News . . . and you’re . . . a . . . Republican.” She asked the Uber driver to stop the car—you can’t make this stuff up—and was going to walk away, at night, in the middle of nowhere. We ultimately agreed to have the driver drop her off safely at home.
Most times, when someone learns I’m a Republican, the reaction is one of dismay or disgust. White folk usually fall within the dismay category (“I assumed you . . .”), while members of the black community, as shown in all three of these examples, often look at me as the worst kind of enemy. A traitor. A . . . you got it, “Uncle Tom.”
Can I blame any of them? The truth is, I don’t. More than a decade ago, I thought similarly.
If you asked what party I belonged to then, I’d have told you I was a Democrat. This had little or nothing to do with my actual beliefs. Rather, I knew this because everyone around me—family, neighbors, friends—was a Democrat, and more than 70 percent of voters keep the same political allegiances as their parents. I knew this because I was black, and almost 90 percent of African American voters identify with the Democratic Party.
I also knew all about the Republicans. All the “facts.”
The ones ingrained in me and many members of the black community since birth. “Republicans are racist.” “They don’t care about black people, don’t care about poor people.” “They want black men in jail—or, better, dead from drugs or gang violence.” “Republicans are the party of racist, rich white people.” “Republicans created and led the KKK.” “They try to keep blacks from voting.” “The GOP intentionally blocks the advancement of blacks and always has.” “If you ever become one, you’ll get kicked out of the family and be an ‘Uncle Tom’ and a ‘coon.’ ”
Maybe you find these accusations and words offensive. I certainly do. Maybe you agree with some of them and think they’re worth debating. All I’m telling you is that this was the narrative as I knew it. At the time, everyone I knew thought exactly the same way. During the formative years of my life, I had no clue what a Republican—or a conservative—even was. As a result, I had no idea who I was politically.
Growing up on the South Side of Chicago, I heard it all the time. From my parents and friends, my teachers, my girlfriend and her grandmother, the guy working next to me. It was always the same spin on things: The Republicans were the “racist party” who spent their days keeping people of color down.
The message even held sway in our churches. For decades, Democratic politicians have gone to pastors in black communities and given them their talking points and marching orders. These pastors see that the Democrats have something they need—sources of income, ways to expand their reach, influence with the mayor—and the next thing you know, some politician is standing in the middle of a service giving a partisan speech. Chicago’s ex-mayor and former Obama chief of staff Rahm Emanuel was infamous for popping into black churches, giving a quick talk, and walking out before the next hymn even started. (How often do you see a black politician speaking in a white church, or any politician taking over a Catholic mass or synagogue service to give a speech? You don’t.) That’s how entrenched the Democrats’ agenda, and falsehoods, were in my community.
So why would I think differently? My family, my friends, my school, and even my pastors at the time were all saying the same things. Where would such differing ideas even come from? More troubling, who would support those ideas if I dared have them?
It wasn’t worth the time to investigate the matter further. The earth was round, wood floats, and the GOP was basically the KKK in better-looking jackets. And “better-looking” was debatable.
Then, one evening, as I was talking on the street with a neighbor I hardly knew, there was a catalyst—or at least the chance for one—that helped change my narrative. I was barely twenty. We were discussing politics, each of us pontificating on this and that, when this older black gentleman openly challenged me on one of my viewpoints.
I don’t remember the specifics of what I’d said, but it had been something nasty about the GOP and some social injustice I’d laid at their feet. Whatever criticism I’d just made, this man didn’t simply let it pass or look the other way when such inaccurate “facts” were being shared. He knew my take was wrong, and he did what few ever do in a closed community: He pushed back. “Where’d you get that?” he said. “That’s not right.”
He mentioned that most black people had once been Republicans themselves. I’d never heard that before, so I didn’t believe it. Out of pure shock that this guy would openly lie to me like that, my tone became more aggressive.
The gentleman held out his hands. “Listen,” he said. “I’m not trying to convert you. I’m a Democrat. But what you’re saying is . . . wrong.”
Whatever defense or counterargument I may have tried that night, it didn’t hold up for long. Clearly this man knew more than I did, so I stopped talking and told myself that he and I would meet again.
Here’s something you should know about me. Whenever I’m challenged, I always go off to find more information, in hopes that I’ll have a stronger argument in the conversations to come. I hoard facts like a magpie preparing for his next debate.
In the eighth grade, for example, if I knew that our teacher, Mr. Horton, was going to discuss a particular subject, I would always research ahead in order to debate him. I wanted to stand out in class. I was the kid who’d scour the dictionary for a word I’d never heard anyone use, just to see if Mr. Horton knew it. Although it was his first year teaching, he always knew the word, and he stayed one step ahead of me in all of our arguments. (Still, this strategy endeared me to Mr. Horton, who believed I had a real future in politics. When I ran for class president and it didn’t look like I was going to win, he informed the class that he’d likely use his weighted vote for a Caldwell presidency, swaying more voters my way.)
At some point, I knew, there would be a round two with the man who’d challenged my...
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