Tim Miller: Obama Accidentally Made the Case for Why Colbert SHOULD Run (Maybe)

Summary

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Podcast Summary: Bulwark Takes

Episode: Tim Miller: Obama Accidentally Made the Case for Why Colbert SHOULD Run (Maybe)

Host: Tim Miller (The Bulwark)
Date: May 7, 2026

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Overview

In this bite-sized Bulwark Takes episode, Tim Miller muses on a viral exchange between Stephen Colbert and Barack Obama, using the moment as a springboard for deeper questions about the Democratic Party’s future, political punditry, and what kind of leader could break through the 2028 race. The episode blends sharp humor with grounded political insights, touching on how pundits so often misunderstand the voters and highlighting Obama’s surprisingly candid comments about messaging—and who might actually be fit to run next.

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Key Discussion Points & Insights

1. Colbert for President?

• Tim introduces the premise after watching the playful Colbert-Obama interview clips, noting the comedic (yet telling) undertones of their mock campaign banter (01:00).
• Key Exchange:
  • Colbert: "A lot of people tell me I should run for president." (01:36)
  • Obama: "Well, you certainly have the look...the hair...I think that you could perform significantly better than some folks that we've seen." (01:42–02:12)
  • Colbert: "Is that an endorsement?"
    Obama: "It was not." (02:16–02:18)
• Tim laughs at Obama’s jab, speculating with genuine curiosity: “Who is he thinking of?”—pointing out the not-so-subtle critique of certain past or even current political figures (02:21).

2. Political Experience, Entertainment, & Breaking the Mold

• Tim reflects on how “the bar has changed” for presidential candidates, arguing that after Trump, the range of plausible backgrounds for candidates has widened (02:21).
• He questions the conventional wisdom that parties always seek the “opposite” of the last president, noting the cyclical shifts from Bush → Obama → Trump → Biden, and wonders if Democrats should consider an outsider from entertainment—someone who zags when others zig (03:00–03:50).
• Tim remarks that the party risks running the same “flavors of ice cream”—moderate and populist—with no one daring to be something different. He advocates for a Rocky Road or Cookie Monster entry into the primary:

  “I think somebody should try Rocky Road. I'm really running this into the ground. I think somebody should try Cookie Monster from Creole Creamery because voters just aren't like that.” (04:25)

3. The Perils of Punditry and Political Assumptions

• Drawing on 2016 and 2020, Tim highlights how both Republican and Democratic consultants misread their electorates:

  “All of the smartest, most experienced, wealthiest people in the political consultant class on the Republican side in 2016 were totally wrong.” (03:55)

• He urges that “conventional wisdom” ossifies too quickly in the Twitter/modern era, and that actual voters are much less predictable than party professionals assume (04:10).

4. Democratic Messaging: Speak Like a Real Person

• Tim plays a pivotal Colbert-Obama clip about the state of Democratic communication (07:43).
  • Obama: “What I’m more interested in for Democrats is do you know how to just talk to regular people? Like, we’re not in a college seminar, right? Can you talk plain English to folks?” (07:47)
  • Colbert: “Not only does he talk like a normal person, but...he names what’s obviously wrong...and he goes, we should change that thing.” (08:01)
  • Obama: “That doesn’t make any sense and not have a bunch of gobbledygook around it.” (08:14)
• Tim finds it ironic that Obama—himself once seen as academic and lofty—is now urging Democrats to drop the jargon and connect plainly (08:19).
• He mentions Mamdani (presumably a reference to Zohran Mamdani, a New York State Assembly member known for direct social media), and how both “Obama and Mamdani are so similar...super Democrat would like speak like, do speeches like Obama and talk like Zoron.” (09:30)
• Tim concludes this is a powerful endorsement for outsider candidates who can reach voters outside the “two flavors” narrative.

5. Democrats and Ethics: Obama on Trump’s “Side Hustles”

• Obama jokes that a key reform should be:

  “The president of the United States shouldn’t have a bunch of side hustles that those companies and foreign entities can invest in.” (10:23)

• Colbert responds: “How much of that is just jealous that you didn’t think of selling a sneaker because your sneakers would have flown?” (10:44)
• Tim notes the underlying truth of the joke, contrasting the Obama era’s ethical norms with today’s rampant Trump family profiteering, and how shifting the Overton window on presidential conduct would have drastically changed perceptions in earlier years (11:00).

6. A Lighter Note: The Return of the Tan Suit

• Colbert teases Obama about his “tan suit scandal,” referencing right-wing outrage from Obama’s presidency.
  • Obama: “Listen, I own that tan suit proudly, brother.” (12:21)
  • Colbert: “A shattered nation looked up.” (12:29)
• Tim jokes about how “tan suits work for Black people” and relishes the nostalgia for a seemingly more innocent time in politics (12:36).

  • “He did look fly. And boy, what a flashback to a simpler time.” (12:40)

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Notable Quotes & Memorable Moments

• Obama: “You could perform significantly better than some folks that we’ve seen.” (02:03)
• Tim Miller: “Who is he thinking of? I really want to know...” (02:21)
• Tim Miller: “Somebody should try Rocky Road...voters just aren’t like that.” (04:25)
• Obama: “Do you know how to just talk to regular people? Like, we’re not in a college seminar.” (07:47)
• Colbert: “How much of that is just jealous that you didn’t think of selling a sneaker because your sneakers would have flown?” (10:44)
• Obama: “I own that tan suit proudly, brother.” (12:21)
• Tim Miller: “Tan suits work for Black people...boy, what a flashback to a simpler time.” (12:40)

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Timestamps for Key Segments

• [01:36] — Colbert asks about running for president; Obama’s playful jabs
• [02:03] — Obama’s comment on performing better than others
• [03:55] — Tim on pundits misreading 2016 and 2020
• [07:47] — Obama’s candid take on Democratic messaging
• [10:23] — Obama jokes about Trump’s ‘side hustles’ and presidential ethics
• [12:21] — Tan suit flashback, Colbert and Obama riff
• [12:40] — Tim's commentary on the lighter side of political nostalgia

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Final Thoughts

Tim Miller closes by inviting listeners to weigh in on the idea of a Colbert run, acknowledging the real possibility that voters might want a dramatic switch—or that the party may be deeply averse to anything resembling Trump’s style, even with a liberal comedian. The episode is both a comic relief and a shrewd analysis of political currents, reminding listeners that what seems “impossible” in politics is just what happens the minute you set your expectations in stone.

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Transcript

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[Tim from The Bulwark]

Hey everybody. Tim, over from the Bulwark. I was watching some clips of Stephen Colbert and Barack Obama this morning and I got a laugh out of him. So I wanted to share that with you. We all need a little giggle these days and I think there's also, underneath the jokes, some interesting observations about the direction of our politics that's worth meditating on. So let's watch a couple of the clips together and I will give you my thoughts on the other side. First up, the one that really, really tickled my pickle was Colbert asking the former president what he thought about possibly Colbert 2028. Let's watch.

[Stephen Colbert]

I'm looking for a new gig soon and a lot of people tell me I should run for president.

[Barack Obama]

Well, you certainly have the look.

[Stephen Colbert]

Thank you very much.

[Barack Obama]

You have the hair.

[Stephen Colbert]

Well, for the record, I think it's a stupid idea. How dumb do you think it is for people to say that I should run for president?

[Barack Obama]

Well, you know, the bar has changed.

[Stephen Colbert]

That is true. At times subterranean. So I don't have to limbo so low.

[Barack Obama]

Let me put it this way. I think that you could perform significantly better than some folks that we've seen.

[Tim from The Bulwark]

Right?

[Stephen Colbert]

Yeah,

[Barack Obama]

I have great confidence in that.

[Stephen Colbert]

Thank you very much. Is that an endorsement?

[Barack Obama]

It was not.

[Tim from The Bulwark]

Obama's laughing over his own joke there. But I like my favorite part is when he says that Colbert would perform significantly better than some folks we've seen. I'm dying. I have a follow up with that for him. Who is he thinking of? I really want to know who was in Obama's mind when he was thinking about that, was he thinking about one of the Democratic nominees or somebody that his former vice president or somebody from the primaries of 2020. You know, he had to have somebody in mind when he was thinking about that. This is one of those. Is Colbert joking? Like, I assume he's joking and not really thinking about 2028. And there's some reasons to just dismiss it out of hand as Obama mentioned the fact that he has absolutely no experience for this job and no kind of relevant expertise. But also as was mentioned, neither does the current president. So there's that. And I think that the question is conventional wisdom has been people are looking for kind of the opposite of the previous president. Obama was opposite of Bush in so many ways. Trump opposite of Obama, of course Biden opposite of Trump in kind of a different way that Obama was then went back to Trump. If you don't remember the idea that there would be kind of a lib Trump like an not that Colbert and Trump are like it all beside besides the fact that they come from entertainment, you know, that they're good at the performance part of it, that seems kind of hard to imagine. You'd think that the Democrats would want to zag a different direction. On the other hand, I kind of want somebody to try it. And whether that's Colbert or somebody else, I feel like one area of expertise that I can bring to the conversation about 2028. So you'll probably be hearing me mention this. A lot is looking back at 2016 like the conventional wisdom inside Republican consultant class Republican politician circles was so thick like it whether you talk to Ted Cruz's consultants or Marcos or Scott Walker's or Jeb's or whoever's. Like everybody's analysis of the state of play was like basically the same. Right. What voters were looking for true conservatism, like what the lanes were in the primary, the weaknesses of Trump and everybody's wrong. All of the smartest, most experienced, wealthiest people in the political consultant class on the Republican side in 2016 were totally wrong. And by the way, on the democratic side in 2020, they weren't wrong quite as bad. But people were pretty wrong about what Democratic voters were looking for. And so people aren't as smart as they think. And yet conventional wisdom just especially in the Twitter age, modern political age, congeals so quickly that you're going to end up having, I think, a bunch of Democratic candidates that are just varying versions of two different flavors of ice cream. Like you'll have the vanilla ice cream moderate types and then you'll have the strawberry ice cream Bernie populist wing types and there'll be like 16 vanillas running and three strawberries. And I think that somebody should try Rocky Road. I'm really running this into the ground. I think somebody should try Cookie Monster from Creole Creamery because voters just aren't like that. Super engaged political voters are, but most of the people that are going to vote in 2028 primary aren't like that. And I think that the Democrats should have some people running who are kind of like I'm a little bit strawberry, I'm a little bit of. I have other views that are different and see if something works, particularly if they're very clear eyed about the threat of the right wing authoritarianism and they're able to carry a message about that the way that Trump was. You know, if you have somebody from the outside who's a fighter who doesn't fully map onto the Bernie or Hillary ideology, like that would be the person I would bet on. But I don't see any of them emerging. Is that going to be Stephen Colbert? I don't know, but I think it could be somebody. And it felt like Obama. I don't know, maybe we can get Obama on the pod and follow up on that because it kind of felt like he thought the same thing.

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[Tim from The Bulwark]

And I want to play for you a clip where they're discussing Democratic messaging.

[Barack Obama]

What I'm more interested in for Democrats is do you know how to just talk to regular people? Like, we're not in a college seminar. Right. You know, can you talk plain English to folks about.

[Stephen Colbert]

I think that's one of the powers that Mamdani has.

[Barack Obama]

That's correct.

[Stephen Colbert]

Is that he also. Not only does he talk like a normal person, but he lives a normal life, but he also. He names what is obviously wrong.

[Barack Obama]

Yes.

[Stephen Colbert]

And he goes, we should change that thing.

[Barack Obama]

That doesn't make any sense and not have a bunch of gobbledygook around it.

[Tim from The Bulwark]

It's so funny that it shows you how far afield that Democratic messaging has gotten from how real people talk. That Obama, who was criticized a lot in 2007 and 2008 for being a little highfalutin in his language, being a little academic, he's the one now that's like, could you please talk normal? Could you please just talk like a regular person? Obama was always a bit of a code switcher and kind of could turn on and off, you know, his oratorical style. But even still, like at times, if you even talk to my buddy Favs or, you know, his staff, like, they'd say, at times he's just, he'd get academic in response to questions. And so somebody like that, somebody like Obama who talks in prose and long form, looking at the other Democrats and saying, got to be a little bit more blunt. I think it's telling. And it also speaks to why an outsider I think could do well. They both shout out Mamdani. And it's Mamdani and Obama are so similar in this specific way because they're like inverse. Mamdani is really good in this short term form video coming off like a normal guy, somebody friendly, somebody affable. And then, I don't know, maybe he just needs John Favreau. I don't know who his speechwriters are, but his speechifying is very, you know, Bowdoin barred class president, you know, and he sounds like a liberal elite college rich kid who, you know, ran for class president and has, you know, deep thoughts about systemic structures in our country. And so it's kind of like super, super Democrat would like speak like, do speeches like Obama and talk like Zoron. But anyway, I, I think that, like the broader principle is there that separating from this kind of talking point speak, being more casual, it's something that Democrats could benefit from. And if Obama's saying it, you gotta, you know, it's true. There are a couple other clips that are just funny. Let's get a couple laughs together. We'll watch. First, Obama talking about what are the reforms that he thinks that we should put in place should we ever get out of this Trumpian nightmare.

[Barack Obama]

And then, you know, a good policy that I'd like to see followed is that the president of the United States shouldn't have a bunch of side hustles that those companies and foreign entities can invest in.

[Stephen Colbert]

How much of that is just jealous that you didn't think of selling a sneaker because your sneakers would have flown? You know that, right?

[Barack Obama]

You know, you would bank coin.

[Tim from The Bulwark]

It's the Colbert joke about Obama being jealous that he didn't invest in a snake sneaker. Just kind of like think about how much money Obama could have made at the peak of his powers. Like the Shepard Fairey Obama Hope poster. If the rules that we have now were the rules, right? If Michelle could have just had a side hustle that sold basketball sneakers where she did a deal with Nike. He's rich enough as it is, but they could have made billions upon billions. And so it's like one of, again, it was one of these funny jokes that carries this truth underneath it. It is so insane what the Trump family is doing right now and the fact that it is not leading news every night. And just think about the coverage if Michelle Obama did a Nike deal during 2009, or if the Hope posters were Shepard Ferry and the Obama family did an LLC where they sold them together. It's like it's all people that are talked about. And so I do think people don't like it. And I think that at some level, people know that Trump is a huckster. But I think that you'd be surprised to find out how little people know about how much money the Trump family is actually making off the presidency right now. And I think it's pretty important messaging tactic going forward. Okay, last laugh. We have Obama. We gotta ask him about the tan suit.

[Stephen Colbert]

Is there a wing dedicated to greatest blunders? Is the tan suit here? I'm asking if the tan suit is here.

[Barack Obama]

Listen, I own that tan suit proudly, brother.

[Stephen Colbert]

We have this. If you want to put this on display someplace.

[Barack Obama]

I mean, I look great.

[Stephen Colbert]

A shattered nation looked up.

[Tim from The Bulwark]

You saw that.

[Stephen Colbert]

When you look back at the tan suit, what occurs to you?

[Tim from The Bulwark]

Why he thinks he looks great. In the tan suit. I think he looks pretty good in the tan suit. We can just be honest about this. Tan suits work for black people. I would look very bad. I've tried to put on a tan suit. Not great. So, you know, if. And if you're even paler than me, stay away. Stay away from the tan suit. They're all, you know, you all got to just. You got to deal with the blessings that God gave you. There's certain things that we can wear that other people can't wear, certain things skinny people, muscly people can wear. There's a lot of muscle shirts I wish I could wear that I can't. I can't wear the tan suit. He did look fly. And boy, what a flashback to a simpler time. So, anyway, Colbert 2028. Let me know what you think about Colbert 2028 in the comments. I'm really torn about this. On the one level, I just, I do think that Democratic voters, like, there could be this just deep aversion to anything that even feels at all similar to the Trump model. On the other hand, I don't know, many Democratic voters are like, oh, fuck you. We want to get you back. We'll give you a comedian. We'll see. Let us know what you think. Tell me in the comments. Subscribe to the feed. Tell your friends. Hope you got a laugh out of this. We'll be seeing you soon.

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