I was born Black, and I’ll die Black. I grew up Black, whatever that’s supposed to mean. Raised by Black parents, went to Black churches, and attended Black schools. I lived in a Black community. Simply put, the Black community and culture are in my blood, part of who I am. Now, I’ll be fair—those spaces weren’t exclusively Black. Some of my schools weren’t 100% Black, but most were predominantly so, especially my high school. Why didn’t I lead with that? Had to grab your attention.
The point is, I’m a Black man raised in Black culture. So, what does this have to do with anything? Glad you asked. I come from a long line of Black Democrats. In my family, we’ve always voted Democrat, and I can’t think of a single person who identifies as Republican. Now, that doesn’t mean they don’t exist in the family; I’m just not aware of any. And as you know, as of 2020, around 83% of Black Americans identified as Democrats or leaned toward the Democratic Party, according to the Pew Research Center. It’s a longstanding trend—Black voters are tied to the Democratic Party, with only about 10% leaning Republican.
But as I got older, I started thinking. I was raised Christian too. And here’s where it gets interesting—Republicans seem to align more with some of the Christian values I was taught growing up. Take abortion, for example. The Republican Party typically supports pro-life policies, a stance that resonates with many Christian voters, especially evangelicals. There are other values too, but we’ll save those for another day.
Now, let’s pause for a second. I started out as a Democrat, because of family tradition, but I ended up an independent. That’s a whole topic by itself, but let’s keep moving.
So, what does this have to do with Donald Trump? Well, putting race aside for a minute, the question is: As an American, should I vote for Donald Trump this time around? I sure didn’t help get him in office the first time. Why? I prejudged him. I thought he was racist, and truthfully, I didn’t even know enough about him to back that up. What’s strange is, before he got into politics, I never saw him as a racist. In fact, I remember when rappers—who tend to be Black—used him in their lyrics like he was someone to aspire to. Back then, Donald Trump was just a wealthy man you could look up to. But politician Donald Trump? He came off as racist to me.
Then Trump ran again in 2020, and he lost. Even with that loss, he’s still in the conversation—people either love him or hate him. But for me, the 2020 election hit differently. By that time, I had started my business, but it was still new, just getting off the ground. I wasn’t thinking too much about taxes, regulations, or the things business owners care about when they vote. I was still focused on tradition and what I thought I knew.
But now, things have changed. My business is not just new; it’s successful. And I’ve always been told that if you own a business, you might want to lean more Republican.
But I didn’t want to just jump on the bandwagon because I’m a business owner now. So, I started digging deeper into who Donald Trump really is and what he’s done. What follows is my attempt to break down what I’ve learned.
Donald Trump Loves to Win—And I Can Relate
The first thing that I learned about Donald Trump is that he likes to win. And let’s be real: who doesn’t? I can get behind that. I like to win too, and if you’re in business, winning is the whole game. From what I’ve learned, Donald Trump has spent his entire life obsessed with winning. Whether it’s building skyscrapers, getting his name in lights, or running for president, the man has one goal—winning. And hey, that’s a checkmark in my box for him. There’s nothing wrong with wanting to come out on top. After all, I didn’t build a successful business just to be second place. So yeah, I see eye-to-eye with him on that one. Winning is good.
But here’s where it gets interesting, especially from a business perspective. Trump’s not just about winning—he’s about making big investments to secure those wins. Whether it was Manhattan real estate, his hotels, or even his presidential run, Trump goes all-in. He sees opportunities, makes bold moves, and takes risks. That’s something I respect, because in business, the same rules apply. You don’t win by sitting on the sidelines; you win by investing strategically and being willing to put something on the line.
Think about it: Trump has had successes and failures, but through it all, he’s maintained his brand by playing the long game. Even when he faced setbacks—like when his casinos went bankrupt—he didn’t fold. He regrouped, rebranded, and kept pushing. That’s a winner’s mentality, and anyone who’s ever made serious moves in business knows that persistence and resilience are key to success. If you want to win, you have to be willing to make the kind of investments that position you for long-term gains, not just short-term wins. And Trump? He understands that.
So for me, as someone who built a successful business, I can appreciate that mentality. Winning in business, like winning in politics, requires grit, risk-taking, and a refusal to back down. Trump may be controversial, but when it comes to the mentality of winning, I can relate to that approach. It’s about playing big and staying in the game.
Donald Trump’s Discrimination Lawsuit: A Red Flag?
The second thing I learned about Donald Trump was less encouraging. In the 1970s, Trump and his father were hit with a massive lawsuit for housing discrimination. Uh-oh, right? This kind of backs up my original prejudice: could Trump be racist? Here’s what happened—back in 1973, the U.S. Department of Justice sued Donald Trump, his father Fred, and their company, Trump Management Inc., for discriminating against Black and Hispanic tenants. The government had sent undercover applicants to Trump properties, and what they found wasn’t good. Black people were often told there were no apartments available, while white applicants were shown open units right after.
This lawsuit wasn’t just some minor legal hiccup either—it was one of the biggest fair housing cases at the time, and the evidence was hard to ignore. It came out that property managers working for Trump would mark rental applications with a “C” for “colored” to signal not to rent to Black people. There were even testimonies from employees who said they were directly told not to rent to Black families. One doorman admitted he had to tell Black applicants that the rent was twice as high as it really was. Pretty damning stuff.
Now, instead of settling quietly, Trump did what he always does—he fought back. He didn’t admit any guilt, and even countersued the government for $100 million, claiming they were defaming him. The countersuit was thrown out, but Trump and his team dragged the case on for two years before eventually reaching a settlement. The kicker? Trump never had to admit any wrongdoing. Sure, he had to agree to better policies, but his main goal—like in many of his battles—was to walk away without admitting fault.
So, naturally, this is where my concerns about Trump being racist started feeling justified. The facts from the lawsuit painted a clear picture of discriminatory practices, and Trump’s response wasn’t to own up or make things right—it was to deny, deflect, and fight it out. This moment in his career made me wonder if my initial prejudice had some merit. Was Trump more than just a shrewd businessman? Was there something deeper, something uglier, behind the way he handled his affairs?
Donald Trump’s Surprising Actions That Benefited Black Americans
The third thing I learned about Donald Trump is that, despite my earlier assumptions, he did take actions that benefited Black Americans. This was a curveball for me, especially after the discrimination lawsuits. But looking at his presidency, there were tangible moves he made that had a positive impact on Black communities.
One of the biggest accomplishments was the First Step Act, a criminal justice reform bill he signed in 2018. This law directly addressed issues that disproportionately affected Black Americans. It reduced mandatory minimum sentences for non-violent offenders and gave inmates more opportunities to shorten their sentences by participating in rehabilitation programs. Considering how much the Black community has been impacted by harsh sentencing laws, this was a significant step toward change. Trump took credit for this, and whether you agree with his motivations or not, the results were real.
Another surprising fact was his support for Historically Black Colleges and Universities (HBCUs). Trump signed a bill that permanently allocated $250 million annually to HBCUs, which provide critical educational opportunities for Black students. Now, many presidents before him made promises, but Trump actually followed through with significant funding. Again, this was one of those things that went under the radar for many, but it was a real action that made a difference.
Then, there’s the Opportunity Zones initiative, part of his 2017 Tax Cuts and Jobs Act. These zones offered tax incentives to encourage investment in low-income communities, many of which are predominantly Black. The idea was to spur economic development and job creation in areas that had long been neglected. While the program had its critics, it did direct significant investment into underserved communities.
And let’s not forget the record-low Black unemployment rate during his presidency, which hit 5.4% in August 2019, the lowest it had been in history at that point. Now, you could argue that this trend started before Trump took office, but the fact remains that it happened under his watch. For Black Americans struggling to find jobs, this was a clear, positive result.
I have to admit, this was all unexpected. It didn’t line up with the image I had of Trump going into this. He’s a complicated figure, but these actions show that he did make efforts that, on paper, benefited the Black community. The reality is, things are rarely black and white (no pun intended). Trump’s policies may not have been perfect, but they certainly weren’t all negative, and I had to recognize that.
Wrapping It Up
So, what have I learned? Donald Trump is undeniably a complicated man, and he’s made decisions that pull me in opposite directions. On one hand, as a business owner, I can see why his policies might be compelling. Trump’s focus on winning and making bold moves in business resonates with me. For the first time in my life—I’m a middle-aged Black man who’s always voted Democrat—I’m actually considering voting Republican. That alone feels like a huge shift for me.
But here’s the struggle. Trump has said and done things that I just cannot agree with. His words, his actions—some of them are downright harmful and go against the very values I hold dear. From the housing discrimination lawsuits to his divisive rhetoric, there’s no denying that Trump has done some pretty damning things. Things that are really messed up, to be honest. And this is where the internal conflict comes in for me.
Obviously, there’s much more to Donald Trump than just these three things I’ve learned. It would take a novel to truly capture everything about him because he is indeed a complicated person. But for now, these three points are what stand out the most to me, and they’re forcing me to rethink things in this election.
The election is coming up fast, and I’ve got to make up my mind soon. I haven’t decided yet, but after learning more about Trump, I can say that as a business owner, his approach makes me stop and think. Is it enough to sway my vote? I’m not sure yet, but the clock is ticking, and time is running out.
How about you? Have you struggled with this same decision? If so, I’d love to hear your thoughts. You can email me, leave a comment below, or even drop a comment on Facebook. I need to hear from you. Let me know that I’m not in this alone.