To The Contrary with Charlie Sykes

Episode: Matt Bennett: Lessons Democrats Can’t Ignore
Date: November 18, 2025

Overview

Charlie Sykes sits down with Matt Bennett, Executive Vice President of Third Way, to dissect the lessons that Democrats must confront after recent electoral setbacks and wins. The conversation focuses on the implications of the electoral success of New York City's new mayor, Zohran Mamdani, a prominent Democratic Socialist, and why his victory should not be misconstrued as a model for Democrats nationwide. The episode scrutinizes implications for swing-state races, the necessity for pragmatic moderation, and the challenges the Democratic Party faces in regaining working-class support.

Episode Highlights & Key Discussion Points

Setting the Stage: Who is Third Way and What is "Moderate"?

[01:52 – 04:28]

• Third Way: Founded to define and support center-left, moderate Democrats—not just relics of the 1992 Clinton era, but a movement that's continually evolving.
  • “We regard ourselves as combative centrists and we take a backseat to no one in our loathing of Donald Trump...The guy is destroying everything that we care about and we believe that we have to fight him with everything we've got.” – Matt Bennett [04:28]
• Moderation isn’t a lack of conviction; "combative centrists" also fiercely oppose Trumpism but believe in winning elections through practical means.

Democrats and the Perennial Problem of Learning from Defeat

[06:35 – 07:38]

• Democrats struggle with introspection after losses (2016, 2024) and return to pre-existing approaches, especially those that alienate swing voters.
• The need to focus on how elections are actually won, not just “scratching ideological itches.”
  • “We are big believers in learning from mistakes and learning from losses...but too often...Democrats are kind of immune to change and immune to recognizing where they've really made mistakes.” – Matt Bennett [06:43]

The Mandani Model: What’s Actually Replicable?

[08:44 – 09:52]

• Strengths: Youth, social media savvy, and a sharp focus on affordability (free buses, rent freezes).
• Key takeaway: Simplicity and stickiness of message is good, but promising undeliverable policies risks backlash.
  • “He stuck to one issue, which was affordability...it was a simple, sticky message, and all Democrats should emulate that.” – Matt Bennett [09:01]

Why Mandani’s Victory Isn’t a Blueprint for Swing States

[09:52 – 14:10]

• New York City is not representative; extremely Democratic and liberal.
• Mamdani underperformed predecessors and other centrist Democrats like Mikie Sherrill (NJ) and Abigail Spanberger (VA), even in his own deep blue turf.
• Turnout data show no historic surge in NYC compared to states where moderates won big.
  • “Mamdani ran 18 points behind Kamala Harris where Spanberger ran ahead of her by nine and Sheryl by eight.” – Matt Bennett [12:20]

Working Class and Minority Voters: An Ongoing Crisis

[14:10 – 16:18]

• Mamdani did poorly with nonwhite and working-class voters, winning only a sliver compared to centrists.
  • “Sheryl got 77%, Spanberg got 83%, Mandani got 56% [of nonwhite voters]...He certainly has not [found a way to reach working class voters].” – Matt Bennett [14:10, 15:58]
• Democrats must rebuild bridges with working-class voters; the party is stalling with college-educated Americans and hemorrhaging working-class support.

Who Flips Seats? Not the Far Left

[16:19 – 19:42]

• Historical evidence since 2018: Swing districts are won by moderates, not far left (DSA/Justice Democrats) candidates.
  • “Not a single one of those 40 seats that we flipped from red to blue were flipped by groups that were endorsed by Our Revolution or the Justice Democrats or the DSA or the far left. Every single one of them was either a moderate Democrat endorsed by the New Dems…That’s who wins elections in tough places and flip seats.” – Matt Bennett [17:49]
• Far left models are not only unworkable in purple/red states, they may be “rat poison.”

Republican Strategy: Nationalizing the Far Left

[19:42 – 21:49]

• GOP is adept at nationalizing outlier progressive positions—using wins like Mandani’s to paint all Democrats as “radicals.”
• Past examples like “defund the police” weaponized against moderates.
  • “That is what we’re worried about with Mamdani, with the Democratic Socialists of America, and all of those ideas being weaponized against lots of other people.” – Matt Bennett [20:51]

Messaging for Democrats: How Should Candidates Respond?

[21:49 – 22:23]

• Directness pays: “That was a terrible mistake…What’s going on in New York sure isn’t what’s going on here in Massachusetts…One of the problems I’m going to Washington to fix is that there are radicals in both parties.”
• Candidates must make clear distinctions, reject extreme positions, and connect with local values.

DSA Platform: Why It’s Something to Worry About

[22:23 – 25:05]

• DSA’s (Democratic Socialists of America) platform includes abolishing the Senate, closing jails, ending NATO membership, and more.
• Even if Mandani didn’t run on all these, his affiliation gives fodder to GOP attacks.
  • “Close local jails and free all people from involuntary confinement...defund the police and cut budgets annually towards zero...a second Constitutional Convention to write the founding documents of a new socialist democracy, and finally abolish the U.S. senate—that one I can get behind.” – Matt Bennett [24:14]

The “Boomerang” and “Fox News” Effects

[25:51 – 28:34]

• Defensive “rally around” responses can blind Democrats to problems with extreme positions: “If you hate him, he must be a good guy.”
• “Fox News Fallacy”: Just because the right demagogues an issue doesn’t mean it’s a non-issue.

Language and Relatability: How Democrats Alienate Voters

[36:00 – 39:19]

• Elitist or academic language signals disrespect for working-class voters and feels disconnected.
  • “Do people in the grocery store...say ‘people suffering from incarceration’ or do they say ‘people who are in jail’?” – Matt Bennett [38:53]

The Working Class Deficit: Roots and Fixes

[39:50 – 43:10]

• Causes: Democratic neglect of working-class pain (due to globalization, technology), focus on lower-priority (to them) issues like climate change, and talking down to voters.
• Self-identification gap: Most Democratic strategists/NGOs/philanthropies lack direct connection to non-college or working-poor Americans.

Who Gets It Right?

[43:10 – 44:35]

• Success stories: Alyssa Slotkin (MI), Ruben Gallego (AZ), Richie Torres (NYC), Jake Auchincloss (MA), and Becca Cook (WI). At governor level: Josh Shapiro (PA), Andy Beshear (KY), Wes Moore (MD).
  • “We need more people like her [Becca Cook] that really understand what it is to live a difficult economic life in Congress.” – Matt Bennett [43:36]
• Commonality: They win in swing territories—meaning their approach is applicable nationwide.

Notable Quotes & Memorable Moments

• On moderates fighting Trump:
  “We regard ourselves as combative centrists and we take a backseat to no one in our loathing of Donald Trump.” – Matt Bennett [04:28]
• Explaining the moderate strategy:
  “The only way to really stop and resist Donald Trump is to actually win elections, to win midterm elections, to elect governors, to elect members of Congress, not to scratch your ideological itch.” – Charlie Sykes [05:43]
• On Mamdani’s limits:
  “His policies and message are radical and politically toxic outside the deep blue confines of New York City. They do not translate.” – Charlie Sykes [09:52]
• Data on underperformance:
  “Mamdani ran 18 points behind Kamala Harris, where Spanberger ran ahead of her by nine and Sheryl by eight.” – Matt Bennett [12:20]
• On DSA's radical platform:
  “This is not just generic democratic socialism...You’re not going to find politicians in Denmark, you know, talking this way.” – Charlie Sykes [23:05]
• Advice for swing-district Dems:
  “I think that was a terrible mistake...All of that is crazy. One of the problems that I’m going to Washington to try to fix is that there are radicals in both parties.” – Matt Bennett [21:49]
• Relatability problem:
  “Do people in the grocery store...say ‘birthing person’ or ‘pregnant women’? Like, come on, talk like a normal human being.” – Matt Bennett [38:53]
• Fundamental decision for Democrats:
  “Do you want to win elections or do you want to be ideologically pure?” – Charlie Sykes [33:38]

Timestamps for Key Segments

• Introduction & Third Way’s Role: [01:28 – 04:28]
• Democrats, Introspection, and Learning from Loss: [06:35 – 07:38]
• Mandani’s Model—Strengths and Limitations: [08:44 – 09:52]
• NYC isn’t Swing-State America—The Numbers: [11:00 – 14:10]
• Working Class and Minority Voters Crisis: [14:10 – 16:18]
• Why the Far Left Doesn’t Flip Swing Seats: [16:19 – 19:42]
• GOP’s Nationalization Strategy: [19:42 – 21:49]
• Messaging Strategies for Democrats: [21:49 – 22:23]
• What’s in the DSA Platform: [22:23 – 25:05]
• Fox News/Boomerang Effects: [25:51 – 28:34]
• Language Matters: [36:00 – 39:19]
• Working Class Root Causes & Solutions: [39:50 – 43:10]
• Democrats Who “Get It”: [43:10 – 44:35]

Conclusion: The Core Lesson

Despite the allure of bold left victories in deep-blue strongholds, the evidence and electoral data suggest Democrats succeed nationally when they emphasize pragmatism, relatability, and moderate, persuasive politics—especially with working-class voters. As Charlie Sykes closes:
“It is so crucial to continually remind ourselves that we are not the crazy ones.” [45:52]

For more details, the full text of Matt Bennett’s memo is made available on Charlie Sykes’ To The Contrary newsletter.