Surrounded – Episode 1: Politician vs 25 Undecided Voters (Feat. Pete Buttigieg) | Surrounded Rewind

Podcast: Surrounded by Jubilee Media
Episode: #1
Date: November 9, 2025
Host: Jubilee Media
Special Guest: Pete Buttigieg
Theme: Candid, high-stakes debate where Pete Buttigieg takes on 25 Michigan undecided voters, addressing their concerns about the 2025 presidential race, the two-party system, Kamala Harris, Donald Trump, and the state of American democracy.

Episode Overview

In this inaugural episode, Pete Buttigieg steps into the center of a room filled with 25 undecided Michigan voters, aiming to win them over in a pivotal swing state just days before the presidential election. With voters voicing skepticism, frustration, and hope, Buttigieg addresses a series of tough, nuanced questions on leadership, policy, partisanship, and the very nature of democracy. The tone is direct, earnest, and deeply conversational, with frequent pushback and searching follow-ups.

Key Discussion Points & Insights

1. The Candidates’ Motivations: "Why Are They Running?"

Timestamp: 02:00–13:30

• Pete Buttigieg’s opening claim: "Donald Trump is only running for president for himself. Kamala Harris is running for president to make your life better."
• Voter Pushback: Skepticism prevails about whether any major politician is truly selfless, breeding distrust in the system at large.
• Memorable Exchange:
  • Undecided Voter (Sailor, 05:45): "Anybody that’s in politics is doing it for themselves, if we’re being honest."
  • Buttigieg (06:20): "Yeah, I mean, I get what you’re saying… but I really feel that the things she’s putting forward are more about solving our problems."
• Third-Party Discussion: Some voters voice support for Jill Stein, citing environmental priorities and a desire to break the 'insanity' of repeating the same two-party stalemate.
• Buttigieg counters:
  • Buttigieg (10:20): "Jill Stein is not going to become President… All the things from an environmental perspective… these are not like little differences. You’ve got one set that’s saying climate change is a hoax."

2. Character, Bias, and Trust

Timestamp: 13:30–20:00

• Doubts about Harris' Authenticity: Multiple voters cite Kamala Harris’s reputation for "word salad" responses, struggling to connect with her or see her genuine beliefs.
• Buttigieg defends her approach:
  • Buttigieg (17:50): "She’s the kind of person who would say, here’s what I’m leaning toward doing. Tell me the best argument against doing that. I just can’t picture Trump ever doing that."
• Concerns about Buttigieg’s bias:
  • Voter (18:55): "Do you think you have a little bit of an innate bias because you know her… well or somewhat well?"
  • Buttigieg (19:00): "Well, I’m definitely on her side, obviously… but there are people in my party who I don’t think of as kind of the ideal public servant."
• Voter Disconnection:
  • Voter (19:40): "I see interviews or different questions… I feel like she, like, I’ve seen this called word salad… I don’t feel like I can get an impression of what she really is believing."

3. The Economy & Manufacturing in the Midwest

Timestamp: 25:00–37:30

• Claim: "The economy, especially here in the industrial Midwest, will be better off under Kamala Harris."
• Concerns about messaging:
  • Voters feel Harris talks more about housing/tax credits than manufacturing, while Trump "talks a good game about manufacturing."
• Buttigieg’s Response:
  • Buttigieg (27:20): "There was a manufacturing recession under Trump, even before COVID… Right now there’s more investment in putting up factories in the United States than any time in the last 50 years."
• Broader Economic Frustration:
  • Voter (32:30): "You can’t have a strong economy if everybody can’t afford things… soft monopolies everywhere… Why are we having problems? It’s because people can’t afford anything."
• Policy Nuances: Harris’s platform includes child tax credits, affordable housing, and supply-side interventions, while Trump’s focus is on tariffs (Buttigieg warns these raise costs).
  • Buttigieg (35:15): "Tariffs have a place up to a point, but the level he’s talking about… will add to the price of things that we buy… about $4,000 more per family."

4. Presidential Power and Partisan Dysfunction

Timestamp: 37:30–45:00

• Presidential Limitations: Voters question how much any president can "actually get done" given consistent Congressional gridlock.
  • Buttigieg (39:10): "For very good reasons, the President doesn’t get to just go and do everything they want… but the powers of the presidency go a lot to whether unions get support… to how a law is interpreted… regulations…"
• On Bipartisanship: Buttigieg points to the infrastructure bill as an example of cross-party cooperation, but concedes that most gains have come via slim margins and tiebreaking votes.

5. Rights, Freedoms, and DEI

Timestamp: 45:00–57:10

• Claim: "Americans will have more rights and freedoms under a Harris-Waltz administration."
• Freedom of Speech Concerns:
  • Buttigieg (47:00): "Donald Trump has said that he wants to revoke the licenses of television networks that have broadcast coverage that he disagrees with. I can't think of a more direct attack on the freedom of speech."
• Pushback on Democrats' Track Record:
  • Voter (51:00): Highlights Democrats’ past failures to codify reproductive rights nationally, making promises but not following through.
  • Buttigieg’s reply (52:00): "But since when does civil rights disappear at state lines? And how is it pro freedom to take away a national protection…"
• Social Media & Free Speech: Discussed but clarified as a distinct issue from governmental censorship. Buttigieg distinguishes content moderation from state suppression.
• DEI (Diversity, Equity, Inclusion):
  • Buttigieg (55:13): "The opposite of diversity is uniformity… the opposite of equity is inequity, and the opposite of inclusion is exclusion… the point of government is to make more people better off without making people worse off."

6. Critiquing the Messenger

Timestamp: 57:15–60:00

• Voters press Buttigieg: Why can he answer clearly, while Kamala Harris sometimes comes off as less genuine or more constrained?
  • Buttigieg (58:00): "She faces some constraints that I don’t… she’s a sitting vice president… with the historic nature of her nomination… that can also make it more challenging."
• Unity as Achievement:
  • Buttigieg (59:00): "Our party is not famous for coming together… but one of the things I respect is that she has brought our party together. And… brought more Republicans into the fold than any Democratic nominee I can remember."

7. Crime and Public Safety

Timestamp: 60:00–73:00

• Claim: "Crime will continue to go down in America if we elect a career prosecutor over a convicted criminal."
• Myth-busting:
  • Buttigieg (61:30): "If it’s happened to you, you don’t care what the statistics are… but if you look at the homicide rate, it went up when [Trump] was in power, went down after Donald Trump got beat."
• Detailed Discussion:
  • Discussion covers gun control, criminal law reform (including rescheduling marijuana), and the role of social determinants in crime reduction. Buttigieg highlights recent policy steps and long-term strategies improving quality of life.
• Voters challenge: What has concretely changed for the better under the Biden-Harris administration to deincentivize crime?
  • Buttigieg (71:10): "Child tax credit that cut child poverty almost in half… replacing all the lead pipes is not sexy… but… is one of the best things we can do that will lead to a safer society and less crime."

8. Finale: Impact and Reflection

Timestamp: 74:00–End

• Voters share their evolving decisions:
  • Many express new clarity or at least a renewed commitment to engaging with the process.
  • Voter (75:34, paraphrased): "Before hearing Pete speak today, I was going to abstain… Now, after hearing him, I'm leaning more towards voting, but it's more because of keeping the other guy out."
  • Some shift to Harris, some still torn, and a few newly firm third-party or Trump votes.
• Buttigieg’s Parting Appeal:
  • Buttigieg (78:10): "If you’re skeptical of him and willing to give her a chance, I’m urging you not just to withhold your vote from him, but to use your power… [to] make sure she becomes the next President of the United States."
• Meta-commentary:
  • "These were all undecided voters who are also very well informed. They're not undecided because they haven't been paying attention… They're undecided because there are a lot of things that they care about, and they're working out how that is going to inform their decision to vote."

Notable Quotes & Memorable Moments

• On two-party system frustration:
  • Voter (12:50): "If the founding Fathers saw what we had today, they would riot with their muskets out of the grave. I mean, they didn't want parties. It's true."
• On climate:
  • Buttigieg (11:40): "Right here in Michigan. Right. We have factories rising out of the ground, making EV batteries that are going to power a different kind of future."
• On the economy:
  • Buttigieg (35:30): "The most important thing now is, okay, yeah, nobody's saying everything's perfect… But then what? Like what happens next?"
• On personal bias and knowing the candidate:
  • Buttigieg (19:00): "Well, I'm definitely on her side, like, obviously. Right. That's why I'm here. But there are people in my party who I don't think of as kind of the ideal public servant."
• On the uniqueness of the format:
  • Buttigieg (76:00): "[Voters] are undecided because there are a lot of things they care about… I helped move some people off the fence or clear up some questions or doubts that they had."

Timestamps for Key Segments

| Segment | Timestamp | |----------------------------------------------|-------------------| | Show Introduction & Setup | 00:00–02:00 | | Candidate Motivations & Trust | 02:00–13:30 | | Character, Bias, and Harris’s Image | 13:30–20:00 | | Economy & Manufacturing in the Midwest | 25:00–37:30 | | Presidential Power & Congress | 37:30–45:00 | | Rights, Freedoms, and DEI | 45:00–57:00 | | Critique of Harris’s Messaging | 57:00–60:00 | | Crime, Guns, and Policy Impact | 60:00–73:00 | | Closing Reflections & Voter Feedback | 74:00–End |

Conclusion

This tense, insightful conversation between Pete Buttigieg and 25 undecided voters captures a pivotal snapshot of American democracy in action. Buttigieg is pressed to defend the record and vision of Kamala Harris while being confronted by deep skepticism about politicians, the two-party system, and American institutions. Throughout, the tone remains candid, smart, and deeply human—anchored by voters determined to cast an informed, conscientious ballot.

Further Reflections

• Engagement: Several voters express that Buttigieg’s direct, specific answers provided more clarity than direct messaging from Harris herself—a recurring challenge for the Harris campaign.
• Impact: The episode demonstrates how a single, skillful advocate can sway ambivalent voters—not always to enthusiastic support, but away from abstention or the opposition.
• Final Word:
  • Buttigieg (77:30): "I’m not just here talking about what I believe in blocking, but what I believe in building… if you’re skeptical of him and if you’re willing to give her a chance, I’m urging you… to make sure she becomes the next President of the United States."

For anyone considering their vote, or simply invested in American political dialogue, this episode is an uncommonly raw look at what undecided America is grappling with, and how dialogue—not just advertisement or outrage—can still shape our political destiny.