'Republicans could be woke': A Black conservative from Chicago's South Side makes the case for ditching Democrats

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Former President Donald Trump arrives at an airport.

CHICAGO — There may be a Trump Tower right in the middle of Chicago, but voters here are no more amenable to Donald Trump’s brand of politics than the residents of his native New York. In 2020, Trump won only a single ward in the city, the 41st, on Chicago’s northern edge.

One of the more surprising of the 558,269 votes for Trump in Cook County — which includes Chicago and some of its suburbs — came from the South Side, a majority-Black area that is among the most reliably Democratic sections of the city, as well as the onetime home of former President Barack Obama.

It came courtesy of Devin R. Jones, who heads the Southside Republicans, an organization he founded in 2000. “Fix Where We Live” goes the organization’s motto, alluding to decades of official disinvestment and neglect.

A native South Sider who served in the Navy, Jones is unapologetic about his conservative beliefs. If anything, he thinks that many Black Americans would benefit from Republican policies, if only the national GOP stopped waging culture wars and focused instead on economic empowerment and policies.

Republican politics is especially moribund in Chicago, whose most famous GOP candidate for many years was simply known as Spanky. At the same time, Black voters are showing signs of disenchantment with Democrats. If that trend holds, Chicago could present an opportunity for Republicans to court Black voters.

Yahoo News spoke to Jones with the Chicago mayoral runoff looming. Moderate Paul Vallas is facing off against progressive Brandon Johnson, in a race widely seen as having national implications. The conversation has been edited for clarity and brevity.

Devin R. Jones holds a microphone as he speaks.
Devin R. Jones. (Southside Republicans)

What made you start this organization?

Being a native South Sider, I had never had an option. Oftentimes, there weren’t even Republicans on the ballot. And so I felt that, as Americans, we deserve, at the very least, a two-party system. We deserve options.

Some people would say that the Republican Party, despite becoming more diverse in recent years, is mostly attuned to white concerns.

People would say that, but it’s a party that was founded for Black liberation. Frederick Douglass was a huge Republican. Booker T. Washington. Ida B. Wells, who was a native Chicagoan and Second Amendment rights proponent.

Even [former President Richard] Nixon won with a sizable Black vote.

Do the Democrats take the Black vote in Chicago for granted?

Absolutely. And the Republicans allow it to happen. There are no policies from the Republican Party in the state that address Black people.

Do the Democrats deserve the Black vote?

A man casts his ballot at a polling place.
A man casts his ballot at the United Center in Chicago on Nov. 3, 2020. (Kamil Krzaczynski/AFP via Getty Images)

No, no, no. Not in this city, not in this state. When you go through the South Side, you go to Bronzeville, Englewood, Roseland, the depth of poverty and destruction, the disinvestment, the institutional racism — they have allowed it. We haven’t had Republicans running this area for 100 years.

How would you describe the mood of this city ahead of next week’s election?

People are nervous. A lot of people don’t know what to make of this election. People are tired. They are not feeling hope from either camp. There’s no sense of hope. It’s just like, ‘Whichever one we get, we’ll just figure out how to deal with,’ and that’s a terrible place to be.

[Mayor] Lori Lightfoot said that she lost because she is a Black woman.

I think some of the attacks on how she looks were because she is a Black woman. But who cares? I don’t think she lost because people hate Black women. I think she lost because she was not able to win the battlefield of ideas. She was not able to prove why her policies were best.

Chicago Mayor Lori Lightfoot stands at a podium.
Chicago Mayor Lori Lightfoot at an election night rally on Feb. 28 in Chicago. (Kamil Krzaczynski/Getty Images)

Some have said the crime issue has been exaggerated.

It’s not exaggerated. The numbers don’t lie.

Are you afraid for your safety and your property?

I’m not afraid. I carry.

[Jones clarifies he is a legal gun owner.]

Do you know a lot of Black people who carry?

I know more who carry than who don’t. We have seen crime for so long in the Black community, we just know we need to carry.

To you, the Second Amendment is empowering.

That was instilled in me by my grandparents. They grew up in the Jim Crow South, outside of Vicksburg, Miss. They had shotguns to keep the Klan from coming back. I know a lot of people who have similar stories.

Jordan Landis, a Black gun collector, examines a pistol in a gun shop.
Jordan Landis, a gun collector, examines a pistol in EJB’s Gun Shop in Capitol Heights, Md., on March 14. (Andrew Caballero-Reynolds/AFP via Getty Images)

Democrats claim they’re fighting for equity and social justice.

The only thing that will allow for the movement of Black people — and we have seen this throughout history — is for the government to move out of our way.

Did you vote for Trump?

I voted for him the second time. I did not vote for him the first time.

That’s odd, because there are people who voted for him the first time but not the second.

I saw his policies. I saw what he wanted to do. I saw his Platinum Plan, which I don’t think went far enough. But it was more than what the other side offered. Democrats offered lip service — and no tangible policy.

Will you support Trump next year?

[Laughing] No. Absolutely not.

Why not?

He produced a lot of good policies. I just don’t see where he’s going this time. He’s reverted back to his reality TV personality. We have serious political work that needs to be done.

Florida Governor Ron DeSantis speaks at a GOP town hall.
Florida Gov. Ron DeSantis at a GOP town hall in 2021. (Pedro Portal/El Nuevo Herald/Tribune News Service via Getty Images)

What do you think of [Florida Gov.] Ron DeSantis?

I like many of Ron DeSantis’s policies. I am still iffy on his approach to attacking critical race theory. I think, oftentimes, what Republicans do is, they throw the baby out with the bathwater. We have never had Black history taught with American history. So many Americans don’t know that Crispus Attucks, a Black man, was the first person that died in the Revolutionary War. Many people don’t know how impactful Frederick Douglass was on the Republican Party and on Abraham Lincoln.

DeSantis says Florida is where woke goes to die. What do you hear?


“Woke” [is] originally a term for Black people waking up. Republicans could be woke. There’s a lot of Republicans that are woke.

I think I just found your presidential slogan. Whom are you going to support in 2024?

Just based on who’s out there now, it would probably be DeSantis. I’m leaning towards DeSantis. But I am so undecided. Definitely not a Democrat.

I want to ask you about a couple other national figures. I’ll say the name and you give me your impression.

Let’s start with [South Carolina Sen.] Tim Scott.

If I had to choose between DeSantis and Tim Scott, it’d be Tim Scott. I like his policies. He has offered criminal justice reform. He’s staying true to what it means to be a conservative. You don’t really hear him getting into the culture wars. He’s very policy-focused. If he ran, he’d be my top choice.

Senator Tim Scott shakes hands with someone at a Senate committee hearing.
Sen. Tim Scott at a Senate Banking, Housing, and Urban Affairs Committee hearing on Tuesday. (Tom Williams/CQ Roll Call via Getty Images)

[Former Vice President] Mike Pence.

I like Mike Pence. We have a similar vision of faith. I’ve been a fan of Mike Pence since I was a kid.

[Virginia Gov.] Glenn Youngkin.

He’s doing a good job in the state of Virginia. I like his lieutenant governor, Winsome Sears, a lot more. I’d like to see them switch.

Should we be supporting the war in Ukraine?

We need to completely cut that off. That is not for the defense of the United States.

That is not our fight. We have too much going on at home.

That money should stay at home. We can pass bills to send billions of dollars to another country. And then we have a debate about whether Englewood deserves a water system without lead in it.

We need to reallocate resources.

Concertina wire covers the U.S.-Mexico border fence in Nogales, Arizona.
Concertina wire covering the U.S.-Mexico border fence in Nogales, Ariz., in 2019. (Ariana Drehsler/AFP via Getty Images)

Do we need a border wall?

I think there should be whatever is going to close that border to illegal substances and people crossing. Take the entire United States Army and put it across that southern border.

People would say you’re not being an ally to immigrants.

We don’t allow people from Africa to come the way we allow them to from Central and South America. We don’t allow Haitians. I mean, how Haitian migrants are treated when they come illegally is abysmal.

Mexico is not going to allow me to come down there and roam around, homeless. They’re gonna send me back after I spend time in prison.