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Don Lemon
Host, The Don Lemon Show; Political Commentator, The Don Lemon Show

LEMON DROP - Trump Supporter Goes Head-To-Head With Don — Things Get HEATED!

📅 Oct 20, 2026 Don Lemon 37 MIN 9336 VIEWS 108 SEGMENTS · 4 SPEAKERS
Things get heated as conservative activist and outspoken Trump supporter Michaelah Montgomery goes head-to-head with corporate attorney Diriki T. Geuka, an independent who backed Kamala Harris in 2024. Montgomery rose to prominence as one of Trump's most vocal Black supporters during the 2024 campaign and now says she's open to becoming his next White House press secretary. But what happens when she faces tough questions from Don and a fellow Black voter who sees Trump very differently? From Trump's appeal among Black voters to the political divisions shaping America, Don brings two opposing...

What Don Lemon said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

Don Lemon hosts a debate on why Black voters feel voting won't change anything ahead of the midterms. He argues Democrats are failing to connect with Black voters, pointing to economic struggles and the racial wealth gap. He clashes with Michaela Montgomery over Trump's record, challenging her claims about HBCU funding and opportunity zones, and insists most Black Americans are suffering under Trump's policies. Lemon rejects the 'pull yourself up by the bootstraps' narrative, citing Brookings data showing Black households hold $15 for every $100 of white household wealth. He criticizes Trump's mockery of Abdul El-Sayed's name as racist. Deriki Gayuka adds context on political fatigue and the need for candidates to engage communities beyond election cycles. Lemon concludes by promoting prediction markets like Kalshi for tracking races.

Key takeaways

  1. Lemon says Black households hold $15 for every $100 of white household wealth, citing Brookings data.
  2. Lemon calls Trump's mockery of El-Sayed's name a racist statement, saying Trump 'quacks like a racist.'
  3. Lemon argues most Black Americans are worse off under Trump, rejecting claims of Black economic success as exceptional.
  4. Lemon says Democrats fail to articulate progress and connect with Black voters, leading to political fatigue.
  5. Lemon promotes Kalshi prediction markets, citing El-Sayed at 69% and Rogers at 33% in Michigan Senate race.

Numbers and commitments

FigureWhat it refers toTypeAt
$16 billion Total support for HBCUs cited by Montgomery metric 4:15
$255 million Trump-era HBCU funding cited by Montgomery metric 4:28
69% Kalshi prediction market odds for El-Sayed in Michigan Senate race metric 21:20
33% Kalshi prediction market odds for Rogers in Michigan Senate race metric 21:20
$15 Black household wealth per $100 of white household wealth metric 25:00

Chapters

  1. 0:00Black voters and Democratic failures
  2. 3:39Trump's record for Black voters
  3. 7:27Economic struggles vs. Black wealth
  4. 25:00Racial wealth gap and history
  5. 27:24El-Sayed's Michigan Senate race
  6. 31:00Trump's mockery of El-Sayed's name
  7. 32:37Racism and Trump's behavior

Questions asked in this interview

7
  1. 13:54Deriki, did you hear me say all Black people are struggling?
  2. 17:18Is that where I jump in?
  3. 20:22So, what Black child does not have access to education?
  4. 20:38What Black child doesn't have access to education?
  5. 20:59That's okay. Don, is that your story?
  6. 22:00But how does that get relayed into barbershops, into family reunion conversations?
  7. 36:19Why is a cabinet appointee the only position you can have in the White House?
Don Lemon 0:00 ↗
15 days until the midterms and Democrats need to confront a question that they cannot afford to ignore: Why do some Black voters feel voting won't change a damn thing? MSNBC's reporting from Ohio examines Black men sitting out elections and whether anyone is listening to their reasons. There's also reporting from Michigan that Democrats need to be concerned about, or at least pay attention to. Black voters have long been the backbone of the Democratic Party. So, are Democrats earning that support? And can Republicans offer more than a celebration of Democratic failure? Joining me now, two guests with very different perspectives on that. Michaela Montgomery is a conservative activist and a strategist who became a prominent Black supporter of Trump during the 2024 campaign. She also says she's open to becoming his next White House press secretary. Michaela, we'll get to that in a moment. And then Deriki Gayuka is a corporate lawyer, an independent who supported Kamala Harris in 2024 and president of the Emerging 100 of Atlanta. He has written about understanding Trump's appeal even as somebody who voted against him. Welcome to both of you. Okay. Deriki, I want to get to you. You supported Harris, but you understand Trump's appeal. Why are Democrats failing, if you believe that they are, to hear from Black voters, and what would actually persuade those voters that the party is listening?
Deriki Gayuka 1:19 ↗
Thanks, Don, for having me on. And you know, happy to have served with the Emerging 100, as the immediate past president. I supported Vice President Harris. I supported President Biden when he was president. I think the thing that Democrats have been struggling with is not just paying lip service to Black voters. That's where Trump, you know, as you artfully articulated in the introduction, is excelling at — pointing out all of the faults and mistakes that are real and perceived that the Democratic Party has made. And he's been able to capitalize off that, not so much in getting a swing in support for him, but I think it's effective in blunting the excitement and exuberance that people have when they go to the polls. If you think about, you know, Black people's fight to get the right to vote in this country, you know, over 50 years ago and all the obstacles that stood in our way to go to the polls, and you think about some of the momentous legislation that was passed and the way that the Supreme Court interpreted laws, there was an intense amount of hope that things were going to get better for us over time. And I think they have in a lot of ways. I think Democrats struggle to articulate how things are getting better. We live in a much more diverse society than maybe just, you know, 60 years ago. So they have trouble speaking directly to concerns in the Black community. And I think if you wait until election time to start having those conversations, you're going to have trouble connecting the dots and understanding that the community isn't monolithic, but we do have some shared synergies that need to be addressed. And I don't think that they've done a horrible job at it. I just think that there's always work to be done. And I'm certainly happy to support candidates who are qualified and have competency and want to improve, you know, everyone's station in America, but specifically address some of these long-standing issues in the Black community.
Don Lemon 3:25 ↗
Michaela, you've heard my concerns about the Democrats. Now, can you make the affirmative case for Republicans? What has Trump delivered for Black voters that make their lives better? And specifically, give me specifics if you will.
Michaela Montgomery 3:39 ↗
Okay. Well, we can start with opportunity zones that came in Trump 1.0 that not only boosted economic development but also encouraged the creation of more jobs. We also saw historic funding for HBCUs, and me being someone who works with the White House initiative on HBCUs...
Don Lemon 3:54 ↗
Well, Michaela, hold on. Hold on. The HBCU thing is not real. Joe Biden gave billions more dollars to HBCUs. And that's an argument that I would expect you to make. However, Joe Biden's billions of dollars was split between HBCUs, MSIs, HSIs, and then other minority-serving institutions.
Michaela Montgomery 4:15 ↗
$16 billion in total support of HBCUs.
Don Lemon 4:18 ↗
And all $16 billion did not go to HBCUs. And if we look at the specification...
Michaela Montgomery 4:23 ↗
Stand by, stand by. Let's be honest here.
Don Lemon 4:26 ↗
I thought I was asking a question. My bad.
Michaela Montgomery 4:28 ↗
No, because I like to cut it off before people give misinformation. If you're comparing $16 billion to $255 million, even if that's spread over different things, $16 billion is a much more substantial number in billions of dollars to HBCUs rather than $255 million from the Trump folks.
Don Lemon 4:54 ↗
And as I was saying, I know you guys would love to frame it that way. However, those $16 billion, the majority of it did not go to HBCUs. They actually went to minority-serving institutions, which, as I'm sure you know, are universities that have majority...
Michaela Montgomery 5:07 ↗
Billions more for HBCUs. It's still...
Don Lemon 5:10 ↗
It's not billions more for HBCUs if they have to share the... No, they got less...
Michaela Montgomery 5:24 ↗
I'm speaking.
Don Lemon 5:25 ↗
Yes, sir.
Okay. So, if you're looking at opportunity zones, the American Rescue Plan also offered said opportunity zones and many more opportunities than just the opportunity zones. Again, you're comparing something that is specific that doesn't give much to something that is not specific but says that it's giving a lot and is not.
Michaela Montgomery 5:45 ↗
Well, for you to say it doesn't give much, the fact that it gives something answers your question, because you asked, 'What has Trump done for Black people?' And therefore, I answered your question by letting you know opportunity zones have done a lot to benefit Black people. And as somebody who works with a number of Black mayors, they have all told me how much they love opportunity zones and they're grateful that they're now permanent. And I'd like to keep talking. You have to let me get in here. Okay.
Don Lemon 6:11 ↗
I would have to be able to answer a question.
Michaela Montgomery 6:12 ↗
You are answering a question and we're talking. This is not a soliloquy. Okay. And so if we're having a conversation and you're talking about what someone has given, we're doing it in comparison to Democrats and Republicans giving, or Joe Biden versus Donald Trump. That was the crux of the question. There are certainly things that he has done for the African-American community, but we're talking about the question.
Don Lemon 6:36 ↗
That is a question.
Michaela Montgomery 6:37 ↗
The question wasn't proportionality. The question was what specifically has he done for Black people. And now you don't like it.
Don Lemon 6:43 ↗
No, it's not that I don't like it. I didn't get to finish saying what he did for Black people. I didn't even get to talk about the First Step Act and how we're giving chances to our returning citizens and how, unfortunately for Black men, they disproportionately make up where...
Michaela Montgomery 6:55 ↗
Prison returning citizens is what we call them. We don't call them felons over here on this side. And so if you go to prison and you come out, we believe that you should be able to find a job. You should be able to purchase a home or rent an apartment. And thanks to the First Step Act, these things are now possible for a lot of Black men who are returning home, some of which are returning home for crimes they didn't even commit. So I think that that does a lot in this... and excuse me, I'm misspeaking. I think that that is a great step forward when we're looking at delivering for Black people and actually addressing the things that affect us the most.
Don Lemon 7:27 ↗
Okay. People can't afford rent and mortgages now in...
Michaela Montgomery 7:30 ↗
Is that only Black people?
Don Lemon 7:32 ↗
No. No. Yeah. Well, that affects Black people more. Yeah. I would say specifically it affects Black people more than anybody else because Black people, as you know, according to the facts, are always at the bottom of the totem pole when it relates to economic opportunities, when it relates to inflation, as it relates to prices, jobs. Look at the historic number of Black people who have lost their jobs under the Trump administration. So, if you're talking about returning, okay, fine. You want to talk about people who are returning from the prison system, as you say, or as we say, you don't call them felons. And I'm sure Donald Trump doesn't like that word because that's what they call him or that's what he is. But if you're looking at the overall economy, it is Black people, returning or not, who are much worse off. The general population of Black and white people are worse off now with inflation, with the cost of gas, with a war in Iran and such. So, you know, you're pointing out these things that in a vacuum might mean something, but if you look at it in the overall economy right now, everybody is suffering and those returning people that you're mentioning now are suffering even more under Trump's policies right in this moment.
Michaela Montgomery 8:45 ↗
That's what I mean. When I say proportionality and facts, that's what I'm talking about.
Don Lemon 8:50 ↗
Okay. Well, when we look at proportionality, I don't know what time frame we're comparing it to, but we have more Black millionaires and billionaires than we've ever had ever before. And a lot of them are right here in the United States. For us to talk about how Black people are at the bottom of...
Michaela Montgomery 9:02 ↗
Billionaires compared to the overall population of America.
Don Lemon 9:05 ↗
Okay, hold on. You have, at the end of the day, the overall population. Everybody might not be a millionaire or billionaire, but the fact that we have so many Black people who have reached that status, that lets you know that it is possible. So this whole victim mindset of, 'Oh, Black people are at the bottom of the totem pole, oh my God, we are suffering so bad,' I don't understand how, when Black people... I'm here in Atlanta right now at Level's Mobile Cigar Lounge, a Black-owned business. Black people are opening up businesses, Black people are hiring other Black people. So for us to go ahead and say that Black people are suffering the most, when Black people are creating opportunities for not only themselves, but other people that are a part of their communities, it's interesting. But we can sit here and act like we're all victims. We're super oppressed. We can't do anything because the economy is so bad. Black people literally thrived immediately after slavery was done. And we can open up a university right after emancipation and we can survive in an economy that might...
Can we please stop it? Can you stop like filibustering here? Because I'm wondering if you actually get out and talk to people, especially Black people outside of your bubble, and if you actually see the economic statistics about who is getting what. If we have more Black billionaires, maybe some of them are selling out and buying into these, you know, these economic plans that are not so good for the entire country. However, if you just look at the statistics, the facts, the numbers that don't lie, more people are worse off than better off in the economy, in the environment that we're in right now under Donald Trump's policies. I'm not talking about somebody sitting around a damn cigar bar smoking cigars talking about how well they're doing. Good for them. Most people are sitting at home and not doing well. Most people don't have access to the funds, access to loans, access to the types of... to be in the tax bracket where if they're maybe a millionaire, they can become a billionaire, or if they're a thousandaire, they can become a millionaire. Most people don't have access, they don't have those, as you say, 'pull yourself up by the bootstraps.' Most people don't have bootstraps. And I think yes, people should have a mindset of abundance, but we should also have a mindset of reality. And rather than just sitting around saying, 'Do you go to the cigar bars? Do you actually go to the malls and see the people who are shopping?' That has nothing to do with the actual economy and with the economic numbers.
Michaela Montgomery 11:22 ↗
I've been a community organizer for 10 years. I've been a community organizer for over 10 years. I've done mobilization and engagement for over 10 years in every neighborhood for every socioeconomic class. Therefore, yes, I can speak to exactly how Black America is doing because I actually get out and speak to Black America. Now, I don't know if you get out of your bubble.
Don Lemon 11:40 ↗
Not if you have the bias. No, I'm out every single day talking to all kinds of people. I'm not picking the groups that I'm speaking to. I'm just talking to average everyday people. You know what they tell me? 'I'm doing worse than I was two years ago. The Democrats and Republicans don't care about Black people. We've had them do more for women and members of the LGBTQ or whatever, and this is Republicans and Democrats, they are not for Black men and for Black people.' That's what I'm hearing every single day. And that's not a partisan issue. That is a fact. When you go to a gas station and people say, 'Damn, I can't afford gas.' And you're out here talking about we have more Black millionaires and billionaires. People are going to go, 'F that, I'm not a millionaire nor a billionaire. I'm out here struggling and you're talking about millionaires in a cigar bar.' That's insulting.
Michaela Montgomery 12:27 ↗
You're trying to misconstrue the point that I'm making as if me being in a cigar bar with Black people is apparently a representation of how all Black people are doing. That's not the case. The point that I'm making is Black people own businesses. Black people are here supporting businesses. Black people have money to waste. Therefore, to act like all Black people are at the bottom of this totem pole, to act like all Black people are perpetual victims, to act like all Black people cannot survive an economy that might be going up and down... You can't say that you account for the majority when the majority of Black people I run into are doing a lot better than what you're implying.
Don Lemon 13:00 ↗
Please stop. I'm going to mute you. Okay? Because you're not listening. No one...
Michaela Montgomery 13:07 ↗
Oh, I am listening. Don't tell me that I'm not listening. I am listening. You're saying that all Black people aren't struggling. Of course, I know that. But most of them are. Okay.
Don Lemon 13:16 ↗
You can't say most of them are because they're not.
Michaela Montgomery 13:19 ↗
They are.
Don Lemon 13:19 ↗
No, they're not. Most Americans are struggling.
Michaela Montgomery 13:23 ↗
Most Americans, but not most Black Americans. If we're making it specific to Black people, carrying on the trope that Black people are victims and Black people cannot do better.
Don Lemon 13:32 ↗
You're saying that Black people are better off in this economy than others?
Michaela Montgomery 13:35 ↗
I'm saying Black people are not doing anywhere near as bad as you're trying to imply that they are doing.
Don Lemon 13:39 ↗
No, I'm not implying that they're doing poorly. I'm telling you most people are struggling and Black people are struggling even more than most because of Donald Trump's horrible economic policies. Nowhere did I say everybody or all Black people. You said that.
Michaela Montgomery 13:54 ↗
That's definitely what you were saying. But I will let my friend here, the data guy, the guy who's good with numbers, go ahead and take over. Deriki, did you hear me say all Black people are struggling?
Deriki Gayuka 14:02 ↗
Yeah, I'll jump in. I think what we have is a tale of two cities in the United States. You know, yeah, there's a lot of Black wealth. I think, Don, you were alluding to it. Atlanta has a higher than normal class of Black successful people than you would find in a lot of other major cities. But I volunteer in some neighborhoods in Atlanta that don't look like you're in the United States when you drive through and you see the amount of dilapidation there. I've actually directed a documentary on the power of mentoring because we have so many homes that are struggling in what I would say are disproportionately our communities, and we have work to do as a country at all levels to try to make sure that everyone's station improves. I appreciate where Michaela's coming from because part of being a Black American is having self-determination and a dedication to improving yourself. But I see the split every day. You know, I work for well-off institutions that are doing well, but I see people who, even if their wages have gone up a little bit, inflation has eaten away at their ability to take a vacation. The airline carrier they may have used, Spirit Airlines, is gone. So, they've seen their flights go up, so they can't travel quite as easily during the holidays. And that is a real level of pain even for people who may be doing better, you know, on paper than a generation before them. They aren't doing perfect. They do have stress when they go to the gas station or they go to the pump. And they want to have competent leaders in government that understand that and that can speak to what's happening and that can make the pain go away, because at the end of the day, all of our elected officials have a job to do, which is to make life better for Americans.
Don Lemon 15:54 ↗
Which is to make life better. And I want people... because people misconstrue self-determination with pointing out a few people who are exceptional, like saying, 'Well, look, Tyler Perry is a billionaire, Oprah's a billionaire, Michael Jordan is a billionaire, this person...' Those are the exceptions and they're not the rule. And to point that out is doing a disservice not only to, I believe, Black people, but I believe all people in America. And it's doing a disservice to the Republican Party or Donald Trump, if that's who you support, because you're not being real with people. And people can sniff out BS in a second, just like they are sniffing out now that Donald Trump's economic policies are great for the wealthy. They're great for people who are in a certain income bracket, but they're not great for everybody. Everybody else who's below a certain income bracket and below a tax bracket is losing in this economy. People, you don't care about the economy if you're in a certain tax bracket because you don't care about the prices. But if you're below that, then you have, as you said, Deriki, it is a tale of two cities or a tale of two worlds where you have someone just pointing out the good things. 'Oh, you have more Black billionaires.' I live in a Black city and not everybody's living that way. That's why I say you need to get out of your bubble and actually go speak to people in different places who have an idea of what is going on. Black, white, Latino, Muslim, Christian, whomever.
Michaela Montgomery 17:18 ↗
Is that where I jump in? Because I definitely say that I travel the nation. Again, we keep trying to misconstrue what I would say. I'm not saying that the exceptions are the example. I'm saying that the exceptions prove that it's possible regardless of the circumstances you're in to get out of that and make a lot of money. We didn't have examples like that. Okay. So, for us to say that Black people are at the bottom of the totem pole when we're seeing Black people today become more successful than we've ever seen, own more businesses than we've ever seen, hire more Black people than we've ever seen. How...
Don Lemon 17:49 ↗
Do you know? Give me this. What is the average Black... Are you okay? Did we lose you?
Michaela Montgomery 17:58 ↗
Are we there?
Don Lemon 17:59 ↗
Yeah. No, somebody was trying... I want to ask you, what is the average worth of a Black family? Can you hear me now, Michaela?
Michaela Montgomery 18:08 ↗
Yeah.
Don Lemon 18:08 ↗
Okay. Income-wise, the average Black...
Michaela Montgomery 18:12 ↗
Black net worth is definitely at the very bottom. That has a lot more to do with mindset and cultural differences than the economy. And as somebody who travels everywhere, it has more to do with the lack of information than the lack of access. History has nothing to do with it. History has nothing to do with it.
Don Lemon 18:27 ↗
I've never said that. I said right now, our problem is lack of information and not lack of access to resources. There's no reason why Black people can't all reach a certain standard of living. There's a whole subset of folks who choose to live the way that they live, who choose to ignore all of the resources available to them, who choose not to reach out to the people who could help them. And if you are somebody who travels to different Black communities, then you know that you can come with resources. You can come with help and people will tell you, 'I don't want your help. You're not from here. Go back to where you came from.' That's a cultural issue that has nothing to do with these talks. What president is in power... You got to stop and listen.

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APA

Lemon, D. (2026, October 20). LEMON DROP - Trump Supporter Goes Head-To-Head With Don — Things Get HEATED! [Interview transcript]. Don Lemon. CEOInterviews.AI. https://ceointerviews.ai/interview/3100813/

MLA

Don Lemon. "LEMON DROP - Trump Supporter Goes Head-To-Head With Don — Things Get HEATED!." Don Lemon, 20 Oct. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3100813/.

BibTeX
@misc{lemon2026_3100813,
  author       = {Don Lemon},
  title        = {LEMON DROP - Trump Supporter Goes Head-To-Head With Don — Things Get HEATED!},
  howpublished = {Interview transcript, Don Lemon. CEOInterviews.AI},
  year         = {2026},
  month        = {oct},
  url          = {https://ceointerviews.ai/interview/3100813/},
  note         = {Speaker-attributed transcript with timestamps}
}