Podcast Summary: To The Contrary with Charlie Sykes

Episode: Democrats Need a Winning Formula
Date: February 26, 2026
Host: Charlie Sykes
Guest: Adam Jentelson (Democratic strategist, president of the Searchlight Institute)

Episode Overview

In this episode, Charlie Sykes welcomes Adam Jentelson to dissect the challenges facing the Democratic Party in the wake of Donald Trump's resurgence. The conversation focuses on why Democrats struggle to translate anti-Trump sentiment into electoral wins, the pitfalls of ideological purity and special interest capture, effective responses to populist Republican messaging, and what winning formulas could look like for Democrats in 2026 and 2028. The tone is candid, introspective, and practical, as both discuss specific policy debates, campaign moments, and the broader cultural narratives shaping American politics.

Key Discussion Points & Insights

1. The Democrats’ Core Dilemma: Ideological Rigidity vs. Winning Elections

• Jentelson's Think Tank Mission (02:35–02:56):

  • Adam describes the Searchlight Institute as focused on pragmatic, result-driven policies rather than ideological purity:

    "Our whole thing is breaking free of rigidity and drawing from the best ideas from wherever they come from...being results driven, focused on policy outcomes, and reflecting the will of the American people." — Adam Jentelson (02:35)

• The Trap of Special Interest Groups (03:47–08:00):

  • Democrats are increasingly influenced by special interest and advocacy groups pushing the party to unpopular extremes.
  • Example: The ACLU’s pointed policy questionnaires compelled candidates into extreme stances, like supporting taxpayer-funded gender transition surgery for prisoners or voting rights for the Boston Marathon bomber.

    "What they've done…is that those groups…force Democrats and demand that Democrats take extreme positions...and over the years those positions have gotten more and more extreme." — Adam Jentelson (03:47)

  • The structure incentivizes ideologically extreme positions as a demonstration of organizational influence, not electoral appeal:

    "The way that you show your funders and your board of directors impact is to sort of say, look...look at this crazy position we were able to get Democrats to take." — Adam Jentelson (06:18)

  • These stances have alienated persuadable voters and aided Republican attack ads.

    "Why don't you just write the Trump campaign ads for them?" — Charlie Sykes (07:14)

2. Trump’s State of the Union & The Democratic Response

• Breakdown of Republican & Democratic Messaging (10:24–14:33):

  • Trump played to his base, not persuadables, posting record-low approval ratings post-address.
  • Democrats sometimes fell into Trump’s traps, most notably refusing to stand when Trump declared:
    "The first duty of the American government is to protect American citizens, not illegal aliens." (Viral moment at ~12:00)
  • Jentelson downplays lasting impact but critiques the lack of strategic discipline:

    "If you see your opponent laying a trap, just walk around it...The base isn't going to hammer you for standing up." — Adam Jentelson (13:29)

• State of the Union as an Overrated Event (15:15):

  "People are not paying attention. And people forget what happens at the State of the Union Address or almost immediately two weeks from now." — Charlie Sykes (15:15)

3. Immigration, ICE, & Populist Slogans

• Slogan Politics: “Abolish ICE” and “Defund the Police” (16:31–18:37):

  • Slogans like "Abolish ICE" and "Defund the Police" are toxic outside progressive strongholds.

    "'Defund the police' might be on its own special tier in terms of how toxic it is, but, you know, abolish ICE is still quite toxic..." — Adam Jentelson (18:37)

  • Democrats win when their message emphasizes both enforcement and humane treatment but lose when seen as anti-law enforcement or disconnected from mainstream concerns.

    "We need to win in swing districts and red districts...Abolish ICE could play perfectly well in a place like my home district of Takoma Park, Maryland...but...in states like Michigan...that's going to be absolutely radioactive." — Adam Jentelson (19:14)

• Public Opinion is Nuanced (22:10–25:30):

  • Polls show most Americans support deporting those accused of violent crimes, but not those who came as children or have been long-term residents.
  • Democrats alienate voters when unable to articulate support for both border security and humane policies, unlike, for example, Barack Obama in the late 2000s.

• Message Loss & Party Drift (25:04–26:42):

  "There was a time when the Democratic Party actually knew what the message was and how to sell it." — Charlie Sykes (25:04)

  • Jentelson underscores Democrats lost public trust on immigration by neglecting enforcement while focusing solely on humane policy.

• Who Gets It? Ruben Gallego as a Model (26:50–27:35):

  "Far and away on this issue in particular, [Ruben Gallego] has been Democrats best leader and really does get where we need to be on this issue." — Adam Jentelson (27:35)

4. Economic Message, Populism, and Swing Voters

• Affordability, Working-Class Appeal, and Prosperity (28:29–30:35):

  • Gallego's "big ass truck" line embodies the need for a populism based on economic aspiration, not deprivation:

    "Americans want to get rich...They want prosperity. They want to be successful. They want to own a big ass truck." — Adam Jentelson (28:29)

  • Democrats must balance criticisms of inequality with a positive vision for prosperity alongside holding corporations accountable.

    "As long as we're talking about fairness...holding them accountable when they do bad things. These are all things where we are 100% in the right on policy and in touch with the American people." (32:20)

• Losing the Working Class (32:20–35:41):

  • Democrats became seen as focused on elites’ concerns—climate, social issues, college debt—over traditional bread and butter issues.

    "Democrats have allowed themselves to come across as a party that is more concerned with fighting climate change than with the kitchen table issues..." — Adam Jentelson (33:59)

  • Language like "white privilege" and prioritizing culture war issues (e.g., bathrooms or student loan forgiveness) signals alienation to struggling working-class whites.

• Crowding Out Kitchen Table Issues (37:12–38:32):

  "...our focus on these other issues crowds out the issues that voters are more concerned with...if we have 15 seconds of a voter's attention, what do we want them to hear?" — Adam Jentelson (37:12)

5. Jentelson’s “Roundabout to Damascus” Moment

• Shifting Perspective after 2016 (39:00–41:12):
  • Jentelson describes being to the left of the Democrats he’s served but realized after the 2016 election that ideological purity isn’t a winning strategy.

    "After 2016, when Trump was elected, it felt to me like everything I learned about politics had perhaps been incorrect...so maybe we could throw caution to the wind...there was sort of a period where we experimented with that as a party and it didn't work." — Adam Jentelson (39:00)

  • The conclusion: Democrats must meet the electorate where they are.

6. The Fetterman Question and Intra-Party Friction

• What’s Going on with John Fetterman? (42:14–45:35):
  • Fetterman, once a progressive, now positions himself in opposition to the left as a result of backlash; Jentelson describes this as “negative polarization.”

    "He just sort of decides what his position is going to be based on the opposite of whatever the left wing is saying and what will piss off the left wing of the base the most." — Adam Jentelson (42:41)

  • On Fetterman’s chances in 2028:

    "It doesn't seem like he enjoys the job very much...I'm not sure that he wants it." (45:09)

7. Looking Toward 2028: Big Tent vs. Base Mobilization

• Winning Formula for the Future (47:04–48:23):
  • Jentelson strongly advocates for the "big tent" approach:

    "I want to see a candidate who's got a big vision for winning, not just a majority, but a super majority...that power is going to be what allows us to defeat the rise of fascism in this country." — Adam Jentelson (47:40)

  • He lists a deep Democratic bench, names possible standard-bearers (Andy Beshear, Josh Shapiro, Mark Kelly, Ruben Gallego), but insists the formula must center on broad appeal.

Notable Quotes & Memorable Moments

• On Special Interests and Extremes:
  "Look, basically look at this crazy position we were able to get Democrats to take that demonstrates our influence, right?" — Adam Jentelson (06:18)

• On the Republican Trap During State of the Union:
  "There’s a saying in poker...figure out what your opponent wants you to do and disappoint them. That applies to politics a lot." — Adam Jentelson (13:29)

• On Slogans Like Abolish ICE:
  "Polished ICE could play perfectly well in a place like my home district of Takoma Park...but if you're talking about winning in states like Michigan and Ohio and Texas...that's going to be absolutely radioactive." — Adam Jentelson (19:14)

• On Connecting with Voters:
  "We have to think in a disciplined way. If we have 15 seconds of a voter's attention, what do we want them to hear, and what do we want them to associate with the Democratic Party?" — Adam Jentelson (37:12)

• On the Need for Big Tent Victories:
  "I want to see a candidate who's got a big vision for winning, not just a majority, but a super majority, because that power is going to be what allows us to defeat the rise of fascism in this country." — Adam Jentelson (47:40)

Key Timestamps

• [02:35] — Adam Jentelson on the mission of the Searchlight Institute
• [03:47–08:00] — Special interest group influence and the ACLU example
• [10:24–14:33] — Trump’s State of the Union, Democratic response, and viral moment on immigration
• [16:31–19:14] — “Abolish ICE” and “Defund the Police”—toxic slogans and electoral impact
• [22:10–25:30] — Public opinion polling on immigration nuances, lessons from Obama
• [28:29–30:35] — Populism vs. class warfare, Gallego’s “big ass truck” message
• [32:20–35:41] — Loss of working-class support, focus on elite issues
• [37:12–38:32] — “Crowding out” core economic/bread and butter issues
• [39:00–41:12] — Jentelson’s shift from ideological left to electoral pragmatism
• [42:14–45:35] — Adam’s take on John Fetterman’s transformation
• [47:04–48:23] — 2028 and why Democrats need majorities, not just wins

Conclusion

This episode offers a deeply introspective, occasionally tough-love critique of Democratic Party strategy and messaging. Sykes and Jentelson agree that Democrats must reclaim a broad, populist vision that emphasizes economic opportunity, fairness, and pragmatic governance—avoiding the traps set by both special interest purists and right-wing provocateurs. The question of how to connect with swing voters, working-class Americans, and alienated demographic groups looms large as the crucial challenge for 2026 and 2028. Both urge the party to pivot toward disciplined messaging, practical coalitions, and a big-tent strategy—putting winning and governance above ideological purity.