On with Kara Swisher: Labor Day Special – Hacks On Tap (September 1, 2025)

Overview

This special Labor Day episode features an episode swap: Kara Swisher introduces a recent "Hacks on Tap" conversation hosted by David Axelrod and John Heilemann, with guest Rahm Emanuel (former White House Chief of Staff, former Chicago mayor, and U.S. Ambassador to Japan). The discussion spans Trump’s threats to deploy the National Guard in Chicago, FBI raids on John Bolton, the collapse of Ukraine peace talks, and the high-stakes redistricting battles in Texas and California. The tone is sharp, insightful, and at times humorous, as the hosts dissect political theatre, policy, and implications for the Democratic Party.

Key Discussion Points & Insights

1. Trump and the "National Guard in Chicago" Narrative

• Trump's Rhetoric vs. Reality

  • Trump called Chicago a "killing field," threatening to send in the National Guard. The hosts rebuff this as political theater, emphasizing the city's vitality.
    • David Axelrod: “...I am not into this false depiction of our city as a hellscape. I'm looking out the window at the lake in Grant park and people, you know, enjoying the love, the fine lines of summer...” (04:45)
  • Rahm Emanuel: “We have made progress... but we have persistent problems, like carjacking, like recruitment of officers... Dems should articulate: we're for more police and getting kids, guns, and gangs off the street.” (05:39)

• Trap for Democrats

  • Axelrod and Emanuel agree Trump uses crime and immigration as divisive "go to" issues, preferring to stir cultural conflict rather than propose actual solutions.

• Effectiveness of These Tactics

  • John Heilemann: “He's underwater on [crime and immigration] now... the extremeness... seems to provoke revulsion in the middle of the country.” (08:07)
  • Discussion of how these strategies failed in 2018 and may backfire by making Trump the "focal point of disorder."

2. Public Safety, Visual Politics, and Chicago

• Pritzker’s Response

  • Illinois Governor JB Pritzker’s visual show of unity (Riverwalk appearance with city/state leaders) is lauded.
    • Rahm Emanuel: “The picture is the story.” (11:18)
  • Real solutions cited: violence intervention, afterschool programs, improved technology, and police recruitment—not performative troop deployments.

• Limits of Federal Involvement

  • National Guard interventions are criticized as temporary, performative, and not an actual solution to urban violence.
    • Rahm Emanuel: “That's not a permanent, sustained effort. Invest in... after school programs so kids aren't on the street now that school's back.” (12:03)

3. Crime Policy as Immigration Policy

• The hosts agree that Trump's crime policies in cities like Washington DC are “an immigration deportation policy masquerading as a crime policy.” (14:23)
  • Targeting cities allows ICE quotas to be met, not actually addressing urban crime.

4. Sliding Toward Autocracy and the Use of Federal Power

• Militarization and "Fascism" Concerns

  • Discussion of Trump’s executive order for a “standing SWAT team of National Guardsmen” and the mass deployment of federal agents.
    • David Axelrod: “...These are elements of fascism, these are elements of autocracy.” (18:38)

• Political Motives

  • All panelists see a pattern of Trump centralizing power, politicizing law enforcement, and using division as a tool.
  • Rahm Emanuel: “The common theme... is division in America, pitting one American against another.” (19:27)

• Historical Parallels and Urgency

  • Comparing current maneuvers to political tactics of foreign autocrats; questioning the silent complicity of business and GOP leaders.

5. Redistricting, Election Integrity, and Democratic Strategy

• Redistricting Battles

  • Republicans’ aggressive tactics (challenging census, attacking mail-in ballots, mid-decade redistricting) are contextualized as efforts to suppress accountability.
    • John Heilemann: “Stop the [vote] steal 2026. With all of this armed militarized stuff... it’s very, very dark.” (26:17)

• Democratic Response

  • Debate over how much Democrats should risk extraordinary measures (like California’s mid-decade gerrymander) to counter GOP maneuvers.
    • David Axelrod: “It’s bullshit for anyone to say... it's out of order and we shouldn't do that. What Newsom is doing is the right thing.” (44:15)

• Potential Consequences

  • Rahm: “If [Newsom] did nothing, he'd get killed. These are the choices you have to make.” (46:21)

6. Mailbag – Listener Questions (58:00–65:10)

• Q1: Are Democrats too slow to fight back against "crazy" GOP tactics?
  • Axelrod: Democrats must focus on real issues (cost of living, jobs) while fighting autocracy—must do both at once.
• Q2: Are Republicans overplaying their hand with redistricting—and could they lose "safe" seats in a wave election?
  • Heilemann cites Dave Wasserman: If the national mood turns, "safe" GOP seats can fall if too aggressively drawn.
  • Axelrod: You move voters to shore up some districts but can make others vulnerable in a Democratic wave.
• Q3: Best political advice received?
  • Axelrod: "Washington’s always the last to get the news." & "The higher a monkey climbs on a pole, the more you can see his ass."
  • Heilemann (from his mother): "Don't get arrested and don't get dead."

Notable Quotes & Memorable Moments

• On Chicago's Realities vs. Trump’s Rhetoric
  • Axelrod: “I am not into this false depiction of our city as a hellscape...” (04:45)
• On Trump's Divisiveness
  • Rahm Emanuel: “President Trump never misses an opportunity to divide Americans rather than try to figure out how to make progress on solving some real problems we have.” (05:39)
• On Politicized Crime Policy
  • Heilemann: “This is an immigration deportation policy masquerading as a crime policy.” (14:23)
• On Sliding to Autocracy
  • Axelrod: “These are elements of fascism, these are elements of autocracy. And you slide into these things. You don't just arrive there...” (18:38)
• On Democrats’ Struggle
  • Rahm Emanuel: “I am shocked at the silence and complicitness... literally make the three monkeys look like an active group. I mean they see no evil, hear no evil.” (27:44)
• On Redistricting Risks
  • Axelrod: “If you play by one set of rules and Trump plays by another, that gives him an enormous advantage.” (44:30)
• On Political Longevity
  • Axelrod: “The higher a monkey climbs on a pole, the more you can see his ass.” (66:48)

Timestamps for Major Segments

• 00:00 – 03:00: Introduction; Trump’s “killing field” rhetoric; setup of the Chicago debate.
• 05:39 – 09:00: Rahm Emanuel’s take on crime in Chicago, policy solutions, and Trump’s “trap.”
• 11:18 – 12:34: Pritzker’s Riverwalk strategy, substance vs. optics in crime response.
• 13:25 – 17:12: Immigration policy masked as crime policy; tensions in Washington DC.
• 18:00 – 22:20: Rise of militarization; slide towards “autocracy”; deeper implications.
• 26:17 – 34:17: Redistricting struggles, GOP suppression tactics, and Democratic counter-moves.
• 43:08 – 46:21: Debate on whether Newsom’s gerrymandering move could cost him in 2028.
• 49:04 – 52:27: Predictions on net House seats after redistricting and risk of GOP overreach.
• 58:00 – 65:10: Listener Mailbag (fighting GOP "crazy," redistricting risks, best political advice).

Tone and Style

The conversation is candid, informed, and peppered with dry humor and political realism. The hosts blend analysis, political history, and occasional anecdotes, creating a rich context for understanding current events and their broader implications.

Conclusion

This episode offers a sophisticated, insider’s analysis of the political battles shaping pre-2026 America: Trump’s use of crime for division, militarized federal actions, and high-stakes redistricting. It’s essential listening for anyone tracking American democracy, urban policy, and political power plays.

For first-time listeners:
Expect punchy exchanges, a deeply informed perspective on the mechanics of American politics, and a focus on what matters for both Democrats and the country at large.