Dave Chappelle, Hakeem Jeffries, and the Luxury of Waiting

I wanted more from both men while people were getting hurt. I still do.

I’m frustrated with Hakeem Jeffries.

I’m frustrated with Dave Chappelle.

Not in the same way. Not even close. But recently, my frustrations with Hakeem Jeffries and Dave Chappelle have rhymed in ways that I don’t particularly enjoy.

My frustrations with Hakeem Jeffries have a lot to do with timing.

Hakeem Jeffries is the leader of the House Democratic minority. That means he’s not really in a position to enact much in the way of policy, since that’s largely the domain of the majority party. But he’s still the highest-ranking Democrat in the House, and as such, I’d like to think that he’d be able to use that power to effect some kind of change. [1]

And to be clear, I’m not expecting him to single-handedly drag the entire Democratic Party into alignment with the most progressive wing of the party. That’s not realistic.

By then, another speech was doing very little for me. I knew he opposed what was happening. I wanted him to make it harder for the administration to keep doing it.

There’s only so much you can do when you don’t control the levers of power.

But still.

Alex Pretti and Renee Good

Especially after Renee Good and Alex Pretti were killed by federal immigration officers in Minneapolis, I wanted to see something more from Hakeem Jeffries. [2] His leadership team had already opposed DHS funding without ICE reforms. [3] I wanted to see him harness his position of power as the leader of the House Democratic minority to press his colleagues harder. I wanted to see him organize. I wanted to see him strategize. I wanted to see him use sustained pressure to back up his support for the communities targeted by Trump’s authoritarian, fascist agenda.

But I haven’t seen enough of that. And after watching Jeffries respond to Democrats’ historic midterm victory, I’m left wondering if he even comprehends the full scope of the crisis that millions of Americans currently find themselves in. [4]

Cyberpunk fascist nightmares are supposed to be something you can switch off at the end of the movie. But for millions of Americans, that dystopian future isn’t some hypothetical scenario dreamed up by some sci-fi writer. It’s their reality. Waiting it out until the next election can be a strategic choice for people like Hakeem Jeffries. For people already in its path, that wait can be a death sentence.

My frustrations with Dave Chappelle are a little different.

Dave Chappelle has always had this way of turning the absurdity of powerful people back on them. There’s a reason that his stand-up specials are still so beloved years after their initial release. Dave had a way of making you look at something so commonplace that it almost ceases to register and realize just how goddamn stupid it all is.

But somewhere along the way, watching Dave Chappelle started to make me a little uncomfortable. The jokes themselves bothered me, and so did the audience he seemed to be cultivating. And as Dave has continued to bask in his celebrity and wealth, my discomfort has only grown.

So when Dave Chappelle joked that he’s felt better since Charlie Kirk’s murder, my frustration came back to timing. [5] The joke came just days after Democrats’ sweeping midterm victory. [4] Now he wants to punch up.

That’s what has me looking at Dave and Hakeem together. I wanted to see that fight before we knew how the election would turn out. People were getting hurt then, too. I’m having a hard time finding anything to celebrate in how long it took.

SHOW TLDRCOLLAPSE TLDR

• Hakeem Jeffries: I wanted more, but as minority leader there’s only so much he can do. His leadership team voted against funding DHS without changes at ICE. I wanted them to hold that line and make it costly for the administration to continue to wreak havoc. [3][6]

• Dave Chappelle: his joke about Charlie Kirk came days after Democrats won big in the midterms. It’s not the first time I’ve been put off by the audience he’s courted for what feels like years. I wanted to hear it before we knew how the election would shake out. [4][5]

• Tabitha Speaks: I agree with some of what she’s saying, esp. around being angry on Jeffries’ behalf at Jennifer Welch while questioning his leadership. We shouldn’t hold Black leaders to lesser expectations just because they’re Black. Black voters elected him & can be disappointed with him. [7]

• I don’t care what their intentions are. I care about how they used their platform & when. I have different expectations for a man vying to be Speaker of the House as opposed to a man whose primary goal is to sell out comedy tickets. I’m over justifying their actions to the people suffering in the interim.

I know, I know. Subscription fatigue is real. Honestly asking for subscriptions isn’t my strong suit, aight?

But if I don’t stick up for my own stuff, who the hell is gonna?

I’m not about to sit twiddling my thumbs hoping some Substack Digest editor decides to feature my writing alongside a bunch of cookie-cutter, pretty faced Substackers who would never in a million years write the word “ain’t” in one of their essays.

Nah.

So if you are lovin’ these deep dives and articles the mainstream press will never cover, consider subscribing to my free newsletter. It’s one less way the MSM can manipulate you. And hey, one less time you’ll have to read some Substack Digest featuring Karen’s lackluster, forgettable essay.

Ok, is my jealousy coming out just a lil bit?

I digress.

If for whatever reason you’re not down to subscribe…

RESTACK this biatch and keep reading.

Bye.

Waiting for the gavel

Democrats won control of the House last week, and that will have consequences. It also put Rep. Hakeem Jeffries (D-NY) in line to become Speaker, where he would still have to wrangle a fractious caucus into unity and discipline on votes. [4]

As House minority leader, Jeffries has spent much of his time in opposition to the GOP, which controls the White House. That’s the reality of politics, but it doesn’t mean there’s nothing Jeffries or Democrats can do beyond rallying their troops, racking up donations and otherwise preparing for the next election.

As minority leader, Jeffries did keep the party united on some important votes. [8] It’s what voters elected him and his House Democratic colleagues to do, after all. And while Jeffries deserves credit for the times he kept his caucus in line, he also deserves scrutiny for the times he failed to do so.

One of the first issues that came to mind when thinking about Jeffries’ leadership in the House was July 2025, when the House voted on a “big beautiful bill” that included Trump administration tax and spending proposals. Ahead of the vote, Jeffries took to the House floor for eight hours and 44 minutes in an effort to stop the legislation, a noble and courageous effort on his part that ultimately fell short. The bill squeaked through without a single Democratic vote, passing 218–214. [9][8]

Another vote that stands out to me happened on January 22, 2026, when the House voted to provide funding to the Department of Homeland Security, including the administration’s Immigration and Customs Enforcement agency. Ahead of the vote, House Democrats, including Jeffries, House Minority Whip Katherine Clark and Rep. Pete Aguilar (D-CA), called on Republicans to include guardrails in the bill, such as limiting use of force by ICE agents and requiring body cameras. When Republicans refused, all three announced their opposition to the DHS funding package. [3]

Seven House Democrats broke with that position, voting in favor of the legislation and ensuring its passage, 220–207. Had those seven voted no, with every other vote unchanged, the bill would’ve failed, 213–214. [6]

Both of these votes highlight the importance, and the limits, of party unity, particularly for the minority party, which can ill-afford to squander votes. On the DHS funding package, House Democrats had enough “no” votes to defeat the measure if all House Dems had voted in unison. Instead, seven Dems voted to fund ICE, ensuring that the measure passed. [6]

Those seven House Democrats should be called out for their votes, as should Jeffries, who, in my view, didn’t do enough to ensure that his caucus voted in unison against the DHS funding package.

As Jeffries seeks the Speaker’s gavel, I’ll be watching to see whether he’s willing to call out his own members when they vote contrary to his wishes, or whether, like many a Democratic politician before him, he’ll turn a blind eye to party insubordination when it suits his political needs.

Who gets to call him out?

Tabitha Speaks is an independent political commentator with hundreds of thousands of subscribers on YouTube. [10] And she went the hell off on Jennifer Welch for going after Jeffries. “Who are you? You are nobody,” she said, before telling Welch, “Shut up. Shut up.” In that same discussion, she praised Jeffries’ intelligence, strategy and experience while questioning whether he had the backbone for the job. [7] And this is the kind of thing where I get where Tabitha is coming from. If someone comes after a leader of color that I happen to disagree with on a bunch of issues, I’m still going to want to know if they’d be talking about a white person the same way. Progressives? Yeah, and? You’re still talking about a Black person. I hear you.

Tabitha questioned Welch’s support for Angie Nixon. [7] I will give Welch props, though. She did interview Angie Nixon and encouraged people to check out her website and send a few bucks her way in September. [10]

On his November 9 show, Don Lemon included a clip of Jim Clyburn defending Jeffries’ leadership in the midterm campaign and highlighting how historic it would be to have a Black Speaker of the House for the first time ever. Lemon also challenged Democrats to take the anger seriously. [11]

I want a Black man at that gavel, and I want Jeffries to have an answer for the Black voters who are angry with him. Why should they not be? What has his leadership done for them? What is he willing to hold his colleagues accountable for? We can think Jennifer Welch went too far and validate Tabitha’s anger and still expect an explanation from Hakeem Jeffries on those seven votes.

When Dave started looking comfortable

As a comedian, Dave Chappelle is brilliant. As a businessman, he’s getting on my damn nerves.

In The Closer, Dave Chappelle talked about “team TERF” and likened trans women to white people wearing blackface. [12] It wasn’t just that statement that rubbed me the wrong way. It was that his comments were met with praise and accolades as if he’d stood up to some sort of powerful entity by making them.

He’s a rich Black man telling an audience what it seemed happy to hear about trans women. To my ears, Black trans women, members of the Black community, were conveniently left out of the conversation. Again, punching down is not standing up for yourself or your people.

Fast forward to September 2025 and Dave Chappelle graces the Riyadh Comedy Festival. [13] This event is backed by the Saudi government and Human Rights Watch warns that the festival is being used to whitewash its human rights record. [14] According to HRW, comedians at the festival were urged to speak out for imprisoned activists like Waleed Abu al-Khair, who was then serving a 15-year sentence for his human rights work. [14] Chappelle commented on how it was easier to talk in Saudi Arabia than back in America. [13]

It might be easier for him. He’s a celebrity welcomed on stage by the government. I highly doubt it’s easier for the people HRW was requesting comedians speak out for.

Fast forward again to November 6, 2026, and Dave Chappelle takes the stage at Madison Square Garden and jokes about feeling better since Charlie Kirk’s murder. [5] This is three days after an election that saw Democrats take back Congress. [4][5] His joke drew backlash from Charlie Kirk’s widow, Erika Kirk. [5] To me, that timing looked opportunistic. I wanted more of that aggression aimed at the right before the election.

Dave Chappelle I still think is a brilliant comedian. The Dave Chappelle businessman I’m starting to lose respect for.

At the end of the day, the reason doesn’t matter

I don’t think understanding why they acted as they did changes my mind about whether what they did was OK. Or whether the people who are suffering the consequences of their actions should just be patient.

What I’d like to see is what kind of action Jeffries is willing to take vis-à-vis his caucus. If people in his party say something is having a bad effect on people, will that be something he tries to do something about? And if that means getting into a potentially uncomfortable skirmish with a colleague? Seven Democrats voted for the DHS funding bill his leadership team opposed. [3][6] I’d like to hear what he did about that. I’d like to hear what he expects of them in the future.

I’d like to see Jeffries be the first Black Speaker of the House. That’s something I want. And that tells you something about how invested I am in this man succeeding. I’m not writing about these two men if I don’t still give a damn about them.

I’m glad Democrats won. But what about those who were under the gun while everyone was waiting for Democrats to win? They still have to live with that. I’m getting tired of asking people to extend grace to people who have exponentially more power and money than them.

I’m tired of making excuses for Dave Chappelle. I’m tired of hearing his jokes about trans people and wondering why he can’t talk about something else for once. [12] I’m tired of how comfortable he was talking in Saudi Arabia. [13] I want to enjoy his comedy without thinking about who’s supposed to be laughing at those jokes. But you know what? I’m also tired of wanting that.

Sources

[1] Hakeem Jeffries’ official biography. U.S. House of Representatives.

[2] Evidence-sharing stopped in the Good and Pretti cases. AP, via MPR News. Oct. 23, 2026.

[3] Jeffries, Clark and Aguilar on DHS funding. Joint leadership statement. Jan. 22, 2026.

[4] Jeffries after the midterms. Claudia Grisales, NPR/WVXU. Nov. 4, 2026.

[5] Chappelle’s Kirk joke and Erika Kirk’s response. Variety Australia. Nov. 9, 2026.

[6] For the DHS funding vote, see the House Clerk’s record of H.R. 7147. It’s roll call 42 from Jan. 22, 2026.

[7] TabithaSpeaksPolitics, Morning Chat and Coffee, Nov. 6, 2026. I’m referring to the discussion at 53:21–59:44 and her return to Jeffries at 1:21:10.

[8] The House Clerk’s roll call 190 shows the final House vote on H.R. 1, July 3, 2025.

[9] Associated Press coverage of the bill’s passage, July 3, 2025. This also covers Jeffries’ eight-hour, 44-minute speech.

[10] Jennifer Welch with Angie Nixon. I’ve Had It / IHIP News. Sept. 2, 2026; 26:57.

[11] Don Lemon’s show on Democratic leadership, Nov. 9, 2026. For the Clyburn clip discussed above, go to 39:49–42:48.

[12] TIME’s report on the controversy over The Closer.

[13] Chappelle at the Riyadh Comedy Festival. Variety Australia. Oct. 3, 2025.

[14] Riyadh Comedy Festival and human rights abuses. Human Rights Watch. Sept. 23, 2025.

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