Podcast Summary: To The Contrary with Charlie Sykes

Episode: Ben Wittes: Five Alarm Fires
Date: August 19, 2025
Guest: Ben Wittes (Lawfare)
Main Theme: Navigating U.S. Democracy Under Threat—Ukraine, Trump, Justice, and American Values

Overview

In this gripping episode, Charlie Sykes and Lawfare’s Ben Wittes unpack a tumultuous week in U.S. international relations, focusing on Donald Trump’s controversial summit with Vladimir Putin in Alaska. They explore the cascading impact of this diplomatic pivot on Ukraine, NATO, and U.S. legitimacy, then shift to the crumbling morale and capacity at the Department of Justice, and end with a reflection on the militarization of American cities. Wittes brings on-the-ground protest insights, analytic depth, and a trenchant warning: "We are not the crazy ones" ([50:00]).

Key Discussion Points and Timestamps

1. Ben Wittes vs. The Russian Embassy: Chalk, Protest, and Escalation

[03:23] – [08:31]

• Incident Recap: Wittes attempts a peaceful protest by chalking a Ukrainian flag on the sidewalk outside the Russian embassy, an act previously cleared with the Secret Service.
• Escalation: This time, five Secret Service vehicles and a fire engine intervene due to a false report (alleging he had "lighter fluid").
• Legal Shift: The Secret Service now deems chalking "defacement," threatening arrest if he continues.
• Aftermath: The embassy swiftly washes away the chalk, exposing hypocrisy: "It is illegal for me to draw in sidewalk chalk, but not illegal for the Russians to hose down the sidewalk" ([07:45]).

Memorable Quote:
“Very worried about all the kindergarteners around the city who don’t even know they are criminals when they draw in sidewalk chalk.” — Ben Wittes [07:45]

2. The Alaska Summit: Trump, Putin, and Global Fallout

[08:31] – [16:45]; [16:45] – [25:55]

Optics of Capitulation

• Atmosphere: Putin arrives in Alaska, avoiding international airspace for fear of arrest, yet receives "the royal treatment" from the U.S. president.
• Global Message: Russian media spins it as Putin moving from pariah to hero, with U.S. troops symbolically "bowing."
• Historical Symbolism: The location is inflammatory for Russian and Ukrainian nationalists, given Alaska’s Russian history.

Notable Analogy:
"Imagine that you met with Osama bin Laden in Spain... a very symbolic act." — Ben Wittes [17:35]

Policy Shift and Consequences

• Appeasement without Purpose: Trump reverses the previous U.S. stance—rather than demanding a ceasefire before negotiations, his administration now mirrors Russian priorities.
• European Alarm: NATO and European leaders, blindsided, rush to D.C. to shore up support for Zelensky and Ukraine, fearing a fundamental realignment in U.S. foreign policy.
• Future Costs: Wittes warns this pivot will damage U.S. credibility "for 50 years" ([13:53]).

Memorable Quote:
"This is a no-joke, sea change in the way an entire generation is going to understand the United States." — Ben Wittes [13:55]

3. The ‘Land Swap’ Fallacy and NATO’s Red Line

[25:55] – [29:46]

• False Equivalence: Wittes rebukes Trump’s notion of a “land swap,” arguing it’s a euphemism for Russian conquest ("the way the US conquest of Wisconsin was a land swap").
• Ukrainian/European Resolve: There will be no acquiescence to demands for Ukraine to surrender territory as a precondition for peace; no real “swap” is on offer.

4. Putin, Trump, and Election Deception

[29:46] – [36:49]

• Manipulative Flattery: Putin manipulates Trump by inflaming his obsession with 2020 election legitimacy, feeding narratives about “fraudulent” mail-in ballots.
• Echo Chamber: Trump, echoing Putin, publicly announces plans to abolish mail-in voting, adopting tactics used by Putin to erode democracy.

Key Exchange:
"Now Trump is in effect taking a cue from Vladimir Putin about how to run elections. I mean, for fuck's sake, Ben." — Charlie Sykes [31:08]
"Not that that would take a lot of learning, but Putin… is actually capable of having a poker face. And so he has played on that." — Ben Wittes [32:03]

• Useful Idiot vs. Co-optee:
  • Wittes clarifies intelligence terminology: Trump may not be a literal “foreign agent,” but is definitively a Russian “co-optee”—serving Russian interests, willingly or unwittingly.

Notable Clarification:
"There is no doubt in my mind that he is a co-optee of the Russian Federation." — Ben Wittes [36:43]

5. Justice in Crisis: Panel Insights on DOJ Decay

[36:49] – [44:52]

• Panelists: Wittes moderates a panel with Francis Fukuyama, Ruth Marcus, and Jack Goldsmith at a recent conference.
• DOJ Devastation: Both Marcus (reporting for The New Yorker) and Goldsmith (legal scholar and former OLC head) agree: the crisis at the DOJ is "even more extreme" than has been reported.
• Stark Moment: Goldsmith, usually the most moderate, confirms "no, Ruth, you are radically understating it," highlighting devastation, attrition, and morale collapse in the Department.

Memorable Exchange:
“...coming from him, it was a genuinely startling moment.” — Charlie Sykes [43:01]
“When he says Ruth, who is generally more alarmed than I am, is under-reacting... was a jarring moment.” — Ben Wittes [43:26]

6. Militarization of U.S. Cities: 'Free DC’ and National Guard Concerns

[44:52] – [49:22]

• Troops on American Streets: National Guard and federal law enforcement are now present in D.C. and other cities at the president’s direction.
• Normalization Warning: Wittes reminds listeners not to blame these individuals, who did not sign up for abuse of this sort.
• Direct Action: Calls on D.C. residents to protest nightly at 8pm—banging pots/pans, making noise—under the banner “Free DC.”

Call to Action:
"Go outside your house for five minutes every day at 8 PM... and make some noise. The slogan is Free DC." — Ben Wittes [47:43]

Notable Quotes & Memorable Moments

• On Trump’s Diplomacy:

  "You never, ever, ever need to prostrate yourself before them. You never need to prostrate America before them." — Ben Wittes [11:57]

• On American Identity:

  "We need to keep reminding ourselves: We are not the crazy ones." — Ben Wittes [50:00]

• On U.S. Justice:

  “No, Ruth, you are radically understating it.” — Jack Goldsmith (paraphrased by Wittes) [43:26]

Conclusion

Charlie and Ben end on a resigned but determined note, urging Americans to protest, resist normalization of the abnormal, and remember their core values. Wittes' closing words—"We are not the crazy ones" ([50:00])—sum up the episode’s spirit: a call to critical vigilance and courage amid “five alarm fires.”