Podcast Summary: On with Kara Swisher — “The Long Game with Jake Sullivan and John Finer”
Date: December 25, 2025
Guests: Jake Sullivan (President Biden’s National Security Adviser), John Finer (Deputy National Security Adviser)
Main Topics: U.S.-Venezuela escalation; Trump’s AI chip sales to China; Ukraine/Russia Peace Talks
Episode Overview
In this special cross-published episode of On with Kara Swisher, listeners hear an installment of The Long Game with Jake Sullivan and John Finer. The discussion takes a "long view" of recent global security developments, focusing on:
- The Trump administration’s escalation in Venezuela
- The decision to permit Nvidia AI chip sales to China
- The state of Ukraine-Russia peace negotiations — analyzed through a “red team/blue team” lens
Sullivan and Finer dissect official narratives, hidden motives, and real-world implications. Their deep insider insights and candid, unscripted exchange cut through standard diplomatic language.
Key Discussion Points & Insights
1. Venezuela Escalation: More Than Just Drugs
Segment: 04:24 – 28:15
- Backdrop: The week saw dramatic events in Venezuela—opposition leader Maria Carina Machado’s perilous escape to Norway, expanded U.S. military presence, seizure of an oil tanker, and Trump’s social media announcement designating the Maduro government a foreign terrorist organization and declaring a “total and complete blockade” of sanctioned tankers.
- Escalation Indicators: Deployment of rescue helicopters, refuelers, and seizure ops signal “preparation for operations.”
- Official vs. Real Narrative:
- Official: U.S. seeks to reduce cocaine trafficking.
- Subtext: The real aim appears to be regime change, targeting Maduro directly.
- Quote [07:03] (John Finer):
“All of the trends are in the direction of escalation... Ostensible purpose is drugs, but this is about much more than drugs.”
- Congressional Concerns: Lawmakers express skepticism about the necessity and legality of military actions. Members feel in the dark, unsatisfied after briefings, and wary of being forced to vote.
- Mixed Administration Motives:
- Trump’s unpredictability—he’s historically opposed “endless wars” but is now risking one of the “most unnecessary wars in quite some time” [12:21].
- Florida politics & anti-Cuba sentiment “intersecting with gut instincts about strength and domination” [15:48].
- Quote [15:48] (Jake Sullivan):
“I think this is about something elemental, something almost gut about just strength and domination for Trump.”
- Risks & Possible Scenarios:
- Maduro concedes and leaves.
- U.S. launches strikes; could escalate to a full land invasion.
- Status quo, with continued economic and military pressure.
- Congressional Authorization Unlikely:
- Politicians historically avoid war votes unless forced.
- Likely outcome: Trump “powers through any legal objections, no matter how well founded.” [27:25]
2. Nvidia AI Chip Sales to China: Strategic Folly?
Segment: 29:54 – 51:41
- Decision: Without public negotiation, Trump announces via social media the U.S. will allow Nvidia to sell advanced H200 AI chips to “approved customers” in China, attaching a 25% tariff to “benefit American taxpayers.”
- Domestic Blowback:
- Republicans and national security officials question the logic of empowering Chinese compute capabilities.
- The very same day, Trump’s DOJ touts interdiction of a smuggling network for identical Nvidia chips, calling them “building blocks of AI superiority ... integral to modern military applications.” [35:20]
- Quote [32:34] (Jake Sullivan):
“It’s not the most advanced chip ... but it is quite a powerful chip that can be used for both training advanced AI models and ... for military purposes.”
- Arguments Defending the Move (Devil’s Advocate):
- Keeps China “addicted” to U.S. chips, slows domestic Chinese chip growth.
- Ensures Nvidia’s financial health to fund cutting-edge R&D.
- Overstates the military/security risks.
- Counterpoints (Sullivan & Finer):
- China lags far behind: even under optimistic projections, China’s domestic chipmakers (Huawei et al.) will not catch up for years.
- “Addiction theory” is naïve: China is determined to build indigenous capabilities, remembering its past humiliation in the Opium Wars.
- Nvidia’s profits are at historic highs even with existing export controls; there’s no danger to innovation by keeping chips from China.
- Undermines Western alliance pressure: European manufacturers (like ASML) may demand reciprocal easing, jeopardizing restrictions crucial to U.S. tech leadership.
- Quote [41:14] (Jake Sullivan):
“…These AI chips ... are the building blocks of AI superiority. They’re used to train the most advanced AI models, create new military and intelligence capabilities … what President Trump is doing by allowing the sale of these chips is solving their problem for them.”
- Strategic Cost: U.S. squanders leverage by giving up something for nothing; signals economic chumminess in hopes of “positive climate” for 2026 Trump-Xi meetings.
- Congressional Response: Bipartisan proposals may attempt to reimpose restrictions, sending a significant signal even if unlikely to overcome a Trump veto.
3. Ukraine-Russia Talks: A Red Team/Blue Team Simulation
Segment: 53:51 – 78:06
- Framework: Rather than U.S. "should we deal," Sullivan and Finer role-play Ukrainian and Russian advisors, mapping plausible internal arguments and constraints on both sides of the conflict.
Ukrainian Perspective
-
Deal Terms (as reported):
- U.S./EU “Article 5-like” security guarantees (short of NATO).
- Pathway to EU membership.
- Limitations on Ukrainian armed forces (but still large by European standards).
- Western support for arms and reconstruction funding.
- Ukraine cedes Donbas and potentially more territory.
-
Case For Accepting the Deal [58:25 (Sullivan, as Ukrainian advisor)]:
- U.S. support is conditional; risk of losing weapons/intel entirely.
- Facing military and economic collapse without Western aid—better to lock in best-possible terms now than accept a worse offer later.
- Peace would enable rebuilding and democratic advances free of pro-Russian regions.
-
Case Against the Deal [60:40 (Finer, as Ukrainian advisor)]:
- Ukraine is not “collapsing” militarily; Russian attrition is high.
- $200B in Russian assets may soon become available—leverage to hold out for better terms.
- Public opinion may not support territorial concessions; could threaten Zelensky’s legitimacy.
- U.S. “guarantees” under Trump are unreliable. If they were serious, Ukraine would be in NATO.
- Quote [64:37] (Finer citing German Chancellor):
“The Americans are now very, very ruthlessly pursuing their own interests …”
-
Recommended Ukrainian Approach: Continue negotiations, use impending Russian asset windfall to toughen terms, avoid hard “no” that could trigger Trump’s ire.
Russian Perspective
-
Case For Taking the Deal [68:23 (Finer, as Russian advisor)]:
- Opportunity to pause fighting, consolidate gains while Trump is in office—no future U.S. president as favorable.
- Extracts major concessions: Donbas, de facto Crimea recognition, NATO rollback.
- U.S./EU engagement can help Russia’s battered economy.
- Kremlin controls domestic narrative—“victory” easily sold.
- Western “guarantees” to Ukraine seen as toothless.
-
Case For Rejecting the Deal [73:36 (Sullivan, as Russian advisor)]:
- Russia can achieve its goals on the battlefield; “winning” is more valuable than a negotiated settlement.
- Keeping Ukraine divided, destitute, and unstable is preferable—peace might enable dangerous Ukrainian resurgence.
- War is sustainable for Russia: recruits, economic “muddling” feasible.
- U.S. promises are fleeting; Trump won’t last forever.
-
Conclusion:
Both sides, if acting purely on their “realist” strategic interests (and current battlefield logic), are likely to prolong the fight rather than accept the best available deal.
Memorable Quotes & Moments
-
On the Venezuela buildup:
“[Trump is] probably thinking in his mind, with a show of strength ... I can get a big win on the cheap by bending this country and this dictator to my will.”
— Jake Sullivan, 15:48 -
On Congressional abdication:
“Members of Congress literally said ... ‘Why are you doing this to us? Why are you making us vote, discharge our Congressional responsibility?’”
— Jake Sullivan, recounting Syria AUMF experience, 27:25 -
On Nvidia/China chip sales:
“You have the Trump Justice Department basically making a robust case that selling these chips to China is a massive problem ... on the very day the Trump administration ... says, ‘We are going to sell these chips to China.’”
— Jake Sullivan, 35:20 -
On U.S. leverage squandered:
“We got nothing in return for this ... I don’t know, though, if you’re definitely right that it wasn’t negotiated.”
— Jake Sullivan, 39:35 -
On Ukraine’s dilemma:
“Ukraine should never say a flat no to the Trump administration. Every time that happens, it leads to Trump essentially flipping sides to the Russian position ...”
— John Finer, 65:59 -
On the impasse:
“The odds of a near term deal are not super high … The most we can hope for is that Russia saves us from ourselves ...”
— Jake Sullivan, 76:52
Important Timestamps
- [04:24] Venezuela escalation and motives
- [12:21] Trump’s historic reluctance for military interventions examined
- [15:48] Sullivan’s insight on Trump’s “elemental” quest for domination
- [27:25] Historic Congressional ducking of war votes
- [32:34] Trump’s rationale for Nvidia chip sales to China
- [35:20] Justice Dept. declares Nvidia chips national security imperative (same day as export announcement)
- [41:14] Sullivan summarizes strategic folly of Nvidia decision
- [58:25] Red team/blue team: Take the deal? Ukrainian argument for yes
- [60:40] Ukrainian argument for no; Finer says U.S. narrative is pressuring, not factual
- [64:37] Merkel quote on "Pax Americana" over
- [68:23] Russian arguments for/against a deal
- [73:36] Sullivan’s “push until capitulation” Russian case
Tone & Style
The conversation balances high-level strategic insight, candid behind-the-scenes analysis, and sharp political commentary. Sullivan and Finer’s rapport is direct and unsparing, with healthy doses of skepticism, practicality, and dry wit.
Summary Takeaway
This episode of The Long Game, delivered via On with Kara Swisher, offers a rare window into how senior U.S. national security officials dissect the shifting landscape of great power politics, the real stakes behind headline-grabbing decisions, and the chillingly limited options available to both friends and foes. With crisp analysis, memorable candor, and a methodical approach to each crisis, listeners come away equipped not only with facts—but with frameworks for understanding today’s most urgent strategic dilemmas.