This week, Wes Moore was elected Maryland's first Black Governor. He's only the third Black person in American history to receive the honor of being elected into the position of executive of state. I'm extremely inspired by Wes and all of his accomplishments. And I'm equally terrified.
Once, Wes — then CEO of Robin Hood Foundation, our nation's biggest nonprofit organization dedicated to serving people living in poverty — invited me and four other friends from Baltimore who all have a history of doing community work, just like he does, out on boat ride. Wes being Wes, he would be driving the boat.
"I joined this boat share," Wes told us. "It's so much better than owning a boat because you aren't directly responsible for the upkeep. You learn how to sail and you get a good selection of boats to choose from."
Despite my fear of sinking ships, I hopped aboard with no problem, because I trust Wes. I've always trusted Wes even when I don't trust the murky water we sail across.
That's the day Wes told us he'd be considering a run for governor. None of us were shocked. We've always viewed Wes as the kind of dude who could or should be president.
Before I met Wes in person, I met him by reputation. In 2010, I was undergoing my own personal transformation, trying to transition from decades in the streets to the real world of jobs, credit scores, bills, cheesy cruise ship vacations, polo shirts, creased khakis, stuff like that. And in between my studying, learning, complaining about the system, and trying to properly starch and press my khakis, I happened to be watching "Oprah" when a brother who seemed to have all of my dreams figured out flashed across the screen. That brother was Wes, who was appearing as a guest to talk about his memoir, "The Other Wes Moore."
Dude was perfect at articulating his thoughts and ideas, a skill that I wanted to learn. He had written a book, and I badly wanted to be a writer. He was an Army vet, and while I wasn't going anywhere near the Army, he also graduated from Johns Hopkins University, a school I had dreamed of attending. I would be accepted to that school the following year.
We've always viewed Wes as the kind of dude who could or should be president.
Like a zillion other people who caught his interview with Oprah, I went out and bought the book. "The Other Wes Moore" delivers a first-class lesson in empathy by clearly explaining the ills of the multiple Americas that exist. Wes accomplishes this by writing about himself and a guy with the same exact name as him.
"The other Wes Moore is a drug dealer, a robber, a murderer. I am a Rhodes scholar, a White House Fellow, a former Army officer. Yet our situations could easily have been reversed," he wrote.
"The Other Wes Moore" was a smash because of the way it humanized poverty for so many people, showing how it was much more than an individual's problem — it was an American problem. Moore dispelled the bootstraps myth by not preaching about hard work but instead focusing on the role society plays — how easy it is for a person living in poverty, even a hard worker, to get caught up in the system — and the role luck plays in Black success, and why we all need to fight to change that as a collective. Wes was preaching, even though he wasn't a reverend. This was the first time I thought, this guy could be president.
This happened during Obama's first term, when stories from clean-cut Black men who could articulate their struggles were being considered, I imagine, because we had a guy with the perfect American come-up story in the White House. We didn't see immediate physical changes in our neighborhoods; however, these triumphs — Obama's election, Moore's success in telling his story of perseverance while shining a light on poverty and the role it plays in destroying communities, rather than solely championing himself and his own abilities, gave the rest of us a kind of American optimism we didn't quite have in the previous generation. Guys like Wes and Obama made us proud. That American optimism they promoted helped motivate us to finish college, build stronger bonds with our families, start those businesses, write those books and try. Try to push past what our ancestors went through, and claim a piece of this country for ourselves.
We didn't all win. And we didn't all get it right. Some of us quit; some of us fell back into our old ways. And unfortunately, some of us died with that optimism. But luckily, some of us excelled.
I wanted to write a book that kids loved as well. I didn't know how I could make that happen.
I graduated from John Hopkins University still squeezing that American optimism, not fully knowing what to do with it, when I bumped into a professor from my first semester.
"Mr. Watkins, what's next for you?" she said, adjusting items in her stuffed New Yorker tote. "Still looking to write?"
"I'm doing it," I responded. "I'm going to figure it out."
She patted me on the shoulder. "You'll figure it out. Next Wes Moore?"
"Who knows?" I laughed. I really didn't know. I had been seeing copies of "The Other Wes Moore" all over the Baltimore City public schools I had been working in. The children loved the text because it gave them hope while acknowledging the struggles they faced. I wanted to write a book that kids loved as well. I didn't know how I could make that happen. I also didn't know I'd publish in Salon, Rolling Stone, The New York Times and other outlets just a few years later.
My writing landed me on the cover of Johns Hopkins Magazine about two and a half years after I graduated. That cover brought in emails from all kinds of Hopkins affiliates, telling me, I needed to work with Wes Moore. "Do you know Wes Moore?" they wanted to know. The funniest was a person asking, "Are you the other Wes Moore?" because of my background.
Finally, someone connected us. A popular architect based in Baltimore, Anna Castro, introduced me to Wes Moore via email and group chat. I met Anna at a bar while trading highschool school jabs with a local politician named Bill. (High schools are everything in Baltimore — much more important than colleges. Bill went to City, and I attended the legendary Paul Laurence Dunbar.) Anna chimed in, telling me about the school libraries and cafeterias her company had renovated, showing me the "before" pictures of crumbling city school structures I was used to and then the glowing "after" photos of the spaces she transformed. "I wish you were redoing libraries and cafeterias when I was in school," I told her.
After I confessed to being a writer, someone else at the bar flashed a cover of the magazine and Castro connected me to Wes. The two of us had coffee a few days later.
I admit I was nervous. Even though I had just been featured in a magazine affiliated with a prestigious university, I still kind of felt like I would be exposed as just another street guy who could never beat his own trauma and be tossed back to where I came from. Wes — a dad who dressed like one, the same way I started dressing years later when I became a dad myself — bopped in with a huge grin, speaking to everyone in the coffee shop, giving hugs and shaking hands. Everyone knew who he was and it felt like he knew them as well. When he found me he dived right into the conversation, asking me, "What do you want to do?"
I didn't quite understand the question. I was new in this game with limited opportunities — at least, not enough to be choosy. He started telling me about his newest venture, Bridge EDU, a nonprofit to help first-year college students find the connections and internships they need to graduate. I thought about my first years as a college student and how the culture shock didn't even allow me to last two months. I was almost 30 by the time I made it to Hopkins for my successful attempt at a degree.
Initially, I didn't fully understand what he was saying. I needed money. I couldn't imagine saying no to an opportunity.
By then, Wes had a new book coming out, "The Work," which highlighted people who were actually making a difference in their respective communities. We talked about the book rollout and what that looks like, all of which was new and valuable information to me — the kind of information new writers need and rarely get from seasoned writers because of petty competitiveness. Wes was different. Before we closed out, he asked me again, "What do you want to do?"
"I don't know, everything," I said. "I want to do it all."
"You can't," Wes laughed. Then he got serious. "But I will tell you this: I think you are a great writer, and I just don't say that. You have a bright future and a whole lot of opportunities are going to be coming your way. If you want to put yourself in the best position to be happy, you need to learn how to say no. This may sound crazy to you now, D, but say no, because if you say no, you will have the bandwidth to work on the things you really care about."
We flicked up and parted ways. Initially, I didn't fully understand what he was saying. I needed money. I couldn't imagine saying no to an opportunity. But he turned out to be right. Opportunities started pouring in and I found myself learning how to connect with the projects that spoke to me the most.
I thanked Wes for that advice time and again, and continued to follow his career. As one of the busiest guys I know, he always took time to do everything from offering advice to me and other writers on publishing and media and popping up at all kinds of community events to stopping me at functions to make sure my jacket and tie was right, or my handkerchief was folded correctly. He's a real big brother — the kind of big brother I try to be to other creators coming into this game behind me.
The way Wes expanded America's perspective on poverty and the care he showed to me, that's what resonates with so many voters. I know guys who have never voted — and never cared to vote — stop me to promote Wes' campaign, proudly saying they were registering to vote for him because he spoke at their school, community center, church or youth program back in the day. Wes has real community connections. And that's what scares me about his election. Losing a guy like Wes to the public sector means his energy and attention will have to stretch far beyond people in poverty. He'll have to be governor of the whole state of Maryland, not just the poor people.
The other scary part is that it is 2022, not 1960, and Wes is still only the third elected Black governor in American history. What's even scarier is how Wes is perfect on paper: a graduate of Johns Hopkins, a Rhodes Scholar, an Army vet, a Wall Street banker who left Wall Street to do community work, a family man. Never had a real scandal other than weak and failed attempts made by other politicians to ruin his campaign. Maryland's last governor was just a white Republican white whose dad had been in Congress. But Wes had to be exceptional — perfect — to win. That's how flawed this country is, and why we need a person like Wes working with and directly advocating for us. However, I also understand that we all have to grow.
I trust Wes Moore. If the state of Maryland is the boat he wants to drive, then I trust his vision. I will gladly hop on for the ride.
