Podcast Summary: To The Contrary with Charlie Sykes

Episode: Simon Bazelon: Deciding to Win
Date: November 2, 2025
Host: Charlie Sykes
Guest: Simon Bazelon, lead author of "Deciding to Win" (The Welcome Party)

Episode Overview

In this episode, Charlie Sykes interviews Simon Bazelon, lead author of the influential report "Deciding to Win." The discussion focuses on the Democratic Party’s strategic missteps since 2012, the disconnect between party elites and working-class/swing voters, and what Democrats must do to win elections moving forward. The conversation is a candid, data-driven exploration of how messaging, policy, and party priorities have shifted—and what needs to change to recapture national relevance.

Main Themes & Purpose

• Diagnosing the Democrats’ Electoral Challenges:
  Bazelon's report examines why Democrats have lost ground with working-class and swing voters since 2012, arguing that increasingly elite-driven priorities have alienated key constituencies.

• Rethinking Party Strategy:
  The episode makes the case that winning is a deliberate choice—and requires confronting uncomfortable truths, recalibrating policy stances, and prioritizing issues voters care about most.

• Finding a Path Forward:
  The discussion is not about Democrats becoming Republicans but about reconnecting with the center and emphasizing economic concerns, public safety, and pragmatic governance.

Key Discussion Points & Insights

Establishing the Baseline (04:00–06:00)

• Purpose of the Report:
  Bazelon clarifies the report is for “intra-party” discussion:

  “The entire point of this is not to tell Democrats to become Republicans. It’s to tell Democrats to be the kind of Democrat that used to win elections.” (Charlie Sykes, 03:42)

• Premise:
  The report launches from the proposition that Donald Trump is damaging for democracy and Democrats must win for the country's sake.

  “Donald Trump is damaging our economy and threatening our democracy… We really start from the premise of what is it the Democrats actually need to do in order to win elections.” (Simon Bazelon, 04:16)

How Democrats Lost the Working-Class Voter (05:40–09:00)

• Rise of the Democratic Elite:
  Highly educated staffers, donors, advocacy groups, and pundits have shifted the party’s agenda away from economic issues.

  “We allowed an increasingly out of touch set of donors, staffers, advocacy groups, pundits, loud voices on social media… to have an increasingly great share over our communications, priorities and positions.” (Simon Bazelon, 05:40)

• Shift in Party Language and Priorities:
  Charlie Sykes notes a dramatic pivot in Democratic messaging away from terms like “jobs,” “middle class,” and “economy,” toward “climate,” “justice,” and “transgender.”

  “If you’re not talking about economic issues, people think you’re not talking about things that affect their lives.” (Charlie Sykes, 08:27)

Disconnect with Voters’ Priorities (09:01–12:00)

• Polling and Voter Perceptions:
  Voters overwhelmingly want Democrats to focus on concrete economic and safety issues—Social Security, healthcare, jobs, crime, and border security rank highest; cultural issues lowest.

  “Voters overwhelmingly want Democrats to focus on concrete economic issues… At the bottom, we see more cultural issues that are a little bit more abstract to voters.” (Simon Bazelon, 09:01)

• Perceived Priorities:
  There’s a significant gap between what voters wish Democrats would prioritize (economic and safety issues) versus what they believe Democrats actually prioritize (cultural/identity issues).

Policy vs. Communication (12:00–14:55)

• It’s Not Just Rhetoric:
  Bazelon emphasizes it’s not only how Democrats talk, but the policy stances they’ve adopted—especially on immigration and crime—that are politically damaging:

  “It’s not just a communications issue… It’s also a governance question.” (Simon Bazelon, 12:09)

• Denialism and Voter Alienation:
  Liz Smith’s critique is cited, highlighting how dismissing voters' real anxieties as ‘right-wing talking points’ has driven many to Trump:

  “We stop treating voters like adults… [and] voters noticed that. They thought we weren’t listening to them.” (quoting Liz Smith, 12:47)

The Leftward Shift: A Real Phenomenon (14:12–17:05)

• Denial of Shift Unhelpful:

  “The Democratic party is just legitimately a lot more left wing than it used to be.” (Simon Bazelon, 14:12)

• Concrete Examples:
  The influx of undocumented immigrants and rise in public disorder/crime post-2020 were not Fox News fabrications but real phenomena, ignored at Democrats’ peril.

• Ignoring Pain Points:
  Presenting inflation and crime as mere perception rather than addressing them substantively fueled political backlash.

The Power of Party Branding and the Role of 'Denialism' (17:05–19:45)

• Bad Faith Attacks & Real Branding Issues:

  “You also have to recognize. Yeah, but you do have a branding problem… The degree to which the public believes these attacks is in large part related to how much truth there is in each of them.” (Charlie Sykes/Simon Bazelon, ~17:05–17:51)

• Empirical Data:
  Number of voters seeing the party as “too liberal” jumped by 9% since 2012. This isn’t just perception—it reflects real policy moves (e.g. Medicare-for-All sponsorships grew from 24 to 47 Democrats between 2013 and 2024).

Toxic/Losing Issues and Policy Blind Spots (19:45–21:27)

• Top Pain Points:

  • Immigration policy
  • Public safety/crime
  • Energy policy (particularly gas prices)
  • Certain cultural wedge issues (trans rights, border decriminalization)

  “I think there’s a real question for Democratic elites… if you talk to them, do you think it’s better for gasoline to be cheap or expensive? …A lot of them just, like, legitimately think more expensive gasoline makes sense. Obviously, voters really do not agree with that.” (Simon Bazelon, 19:53–20:28)

• Culture War as a Wedge:
  Issues like taxpayer-funded gender transition for prisoners became damaging national talking points.

  “In 2024…the whole trans issue… sometimes politics does boil down to those really simple things. Are you for me or against me?” (Charlie Sykes, 21:00)

How Primary Politics Skew the Agenda (23:11–25:59)

• The 2019 Pivot:
  Progressive stances in the 2020 Democratic primaries (e.g., decriminalizing border crossings, expanding federal benefits to undocumented immigrants) were not just theoretical—they continue to haunt candidates.

• Polling Illusions:
  Poll-driven assumptions about the popularity of progressive positions (“pollaganda”) mislead party elites about real voter sentiment.

  “A real cottage industry has sprung up among Democrats…pushing polling results that don’t really line up with what we see when voters actually vote.” (Simon Bazelon, 23:35)

The Myth of Demographic Destiny (25:59–28:43)

• The "Emerging Democratic Majority" Fallacy:
  The notion that demographics would automatically yield a progressive future proved false.

• Voter Self-Identification:

  “71% of voters identify as either moderate or conservative…shifts among minority voters are overwhelmingly among the moderate and conservative ones, not liberals.” (Simon Bazelon, 26:54)

• Evidence:
  Black conservative voter support for Democrats dropped from 86% in 2012 to 47% in 2024.

Lessons from Obama vs. Harris: What Changed? (28:43–31:23)

• Comparing Coalitions:

  • Obama won comfortably in 2012, despite being a “historic” candidate.
  • Kamala Harris, also historic, lost all swing states to Trump in 2024.

  “The share of voters who said Kamala Harris was ‘too liberal’ was about 5% higher than for Barack Obama in 2012. The terrain in which the 2012 campaign was fought was quite different… Romney committed himself to a number of extremely unpopular positions on issues that are quite important to voters, which Donald Trump ditched.” (Simon Bazelon, 29:38)

• Republicans Have Gotten Savvier:
  Trump abandoned unpopular policy stances (like attacking Social Security), while the Democratic Party moved left.

The Appeal of Outsiders & The "Strength" Dilemma (31:23–33:44)

• Establishment vs. Outsider:
  There is voter hunger for anti-establishment candidates—but only those who hold majority-backed views on issues like the border and crime.

  “We want outsiders who take positions that voters agree with…on immigration and crime. If you’re an outsider who hates the system but doesn’t believe in border security…that’s not a mix that voters are looking for.” (Simon Bazelon, 32:34)

Rising Democratic Stars & The Wrong Metrics for Success (33:44–35:37)

• Who Actually Wins Tough Districts:
  Those who appeal to swing/marginal voters (e.g., Jared Golden, Dan Osborne) rarely become party celebrities—but these need to be the models for national strategy.

  “The people who are best… at winning in tough races…really struggle to get Democrats to fall in love with them.” (Simon Bazelon, 34:41)

The Perils of Nationalized Politics & Message Discipline (35:37–39:08)

• Nationalization Means Local Extremes Become National Liability:
  Republicans will spend millions to brand the Democratic Party by its most left-leaning figures.

• Message Discipline Matters:
  Zoran Mamdani (NY state legislature) impresses Bazelon for relentless focus on affordability—a lesson for all Democrats.

  “Whatever you want to say about his policy agenda…he is laser-focused on the issues that New Yorkers care the most about… his slogan is about affordability.” (Simon Bazelon, 36:37)

• Mainstream Democrats Must Lead:
  The problem isn’t AOC or Omar, but the mainstream’s out-of-touchness:

  “What’s needed isn’t for senators from states that aren’t D+50 to get mad at the existence of Ilhan Omar and the squad…[it’s] to articulate their own substantive commitments that better match what voters want.” (Simon Bazelon, 38:13)

Future Shock: Will New Issues Redraw the Map? (39:08–44:16)

• The Disruptions Ahead:
  Sykes asks about the potential for issues like AI and wealth inequality to upend current political coalitions.

• AI as a Political Issue:
  Bazelon thinks AI is likely to rise rapidly as a top-tier political concern—and notes unusually strong public anxiety about under-regulation.

  “If I had to pick a single issue…in 2028 or 2032, it might explode onto the scene and become one of the top issues to voters, I absolutely think [AI] would be my number one choice.” (Simon Bazelon, 40:17) “If you ask voters…are you more concerned about overregulation or underregulation of AI? The overwhelming majority…are concerned the government is going to underregulate AI.” (Simon Bazelon, 42:47)

Reaction to the Report & Closing Thoughts (44:16–47:03)

• Types of Response:

  1. The left, hostile to compromise.
  2. Republicans, bewildered it took Democrats this long.
  3. Broadly positive responses from Democratic elites and some progressives.

  “The response to the report was much more positive than I expected. I expected it to be more controversial.” (Simon Bazelon, 44:29)

• Party Paralysis:
  The DNC is “captured by the same elites and the groups” critiqued in the report, unable to undertake genuine self-examination. (Charlie Sykes, 45:35)

• Direct Lineage:
  Bazelon explicitly aligns “Deciding to Win” with the autopsy ethos of Galston and Kamarck’s “The Politics of Evasion.”

  “We see ‘Deciding to Win’ as directly in the tradition of ‘The Politics of Evasion’ …an ethos of fresh ideas and reconfronting some difficult truths.” (Simon Bazelon, 46:02)

Notable Quotes & Timestamps

• “Winning an election is a decision. You make a decision to win, and then you make every decision in favor of winning.”
  — Quoting Nancy Pelosi, cited by Charlie Sykes, 01:55

• “Voters overwhelmingly want Democrats to focus on concrete economic issues.”
  — Simon Bazelon, 09:01

• “The Democratic Party is just legitimately a lot more left wing than it used to be.”
  — Simon Bazelon, 14:12

• “If you live in a blue state or a blue city, it’s just impossible to not notice that there was a real uptick in things like public disorder between 2020 and 2023… Voters not feeling like Democrats took public safety seriously.”
  — Simon Bazelon, 16:03

• “The degree to which the public believes these attacks is in large part related to how much truth there is in each of them.”
  — Simon Bazelon, 17:51

• “The people who are best… at winning in tough races…really struggle to get Democrats to fall in love with them.”
  — Simon Bazelon, 34:41

• “We need to be laser-focused on the issues that voters care about most.”
  — Simon Bazelon (on Zoran Mamdani’s message discipline), 36:37

• “If I had to pick a single issue…that might explode onto the scene and become one of the top issues to voters, I absolutely think artificial intelligence would be my number one choice.”
  — Simon Bazelon, 40:17

Important Segment Timestamps

• Introduction to theme and guest: 01:55–04:00
• Democratic Party’s leftward drift and consequences: 05:40–09:00
• Polling and priorities mismatch: 09:01–12:00
• Rhetoric vs. policy discussion: 12:00–14:55
• Pain points: crime, immigration, energy: 19:45–21:27
• Primary messaging and polling illusions: 23:11–25:59
• Myth of demographic inevitability: 25:59–28:43
• Obama v. Harris/policy differences: 28:43–31:23
• Mainstream vs. outsider candidates: 31:23–33:44
• Examples of effective centrist candidates: 33:44–35:37
• Party branding and message discipline: 35:37–39:08
• AI, future shocks, and preparedness: 39:08–44:16
• Reactions to 'Deciding to Win': 44:16–47:03

Tone & Style

The episode is frank, data-driven, and urgent. Both Sykes and Bazelon balance critique with a sense of loyalty to the party’s success, adopting a tone that’s critical but constructive, frustrated but hopeful. The discussion is filled with pragmatism rather than polemics.

Conclusion

Simon Bazelon’s “Deciding to Win” provides a sharp diagnosis and actionable prescription for Democrats: prioritize economic and safety concerns, listen to moderate and working-class voters, rigorously question internal polling and messaging, and embrace the tough work of confronting intra-party denialism about increasingly unpopular positions.
As Sykes concludes, “we are not the crazy ones”—but being less crazy isn’t enough; now, it’s time for Democrats to make the hard choices required to win again.