Interview Only w/ Anne Applebaum - Why Putin Won’t Stop, And Why Ukraine Won’t Settle

On this episode of the Chuck ToddCast, Chuck is joined by Pulitzer Prize–winning journalist Anne Applebaum for a sweeping, unsparing look at the state of the Russia–Ukraine war and the global democratic landscape it threatens. Applebaum breaks down whether a ceasefire is even plausible this year, given Vladimir Putin’s unwavering war aims, the murky negotiators involved in back-channel talks, and Trump’s unusually warm posture toward the Kremlin. She details why Ukrainians refuse to accept a “kick the can” peace deal, how corruption scandals are playing out domestically, and the way drones, energy strikes, and a collapsing Russian economy are reshaping the battlefield. From mysterious elite deaths to China’s strategic support, Applebaum outlines the brittle yet dangerous architecture sustaining Putin’s regime.

The conversation widens into a broader examination of the worldwide struggle between democracy and autocracy—from Trump’s Venezuela maneuverings to Saudi Arabia’s complicated role, from Silicon Valley’s unchecked power to Europe’s scramble to recalibrate its alliances. Applebaum warns that the U.S. walking away from Ukraine would reverberate far beyond Eastern Europe, and she explains why the speed and scale of Trump’s attacks on democratic norms have raised historic alarm. It’s a candid, far-reaching assessment of the forces shaping global stability—and the stakes ahead.

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Timeline:

(Timestamps may vary based on advertisements)

00:00 Anne Applebaum joins the Chuck ToddCast

01:45 Will we get a ceasefire this year between Russia & Ukraine?

02:15 Putin has never said he’ll give up original war aims

03:30 Serious concerns about negotiators involved in secret peace deal

04:15 Talks have mostly concerned trade deals between U.S. & Russia

05:00 Putin knows he’ll never have a more supportive U.S. president

06:15 Putin holds a special status with Trump

07:00 Ukraine is more reliant on Europe than U.S. for the war

07:45 Is the corruption scandal involving ministers imperiling Zelensky?

08:45 Zelensky hasn’t gotten in the way of corruption investigation

10:15 Ukrainians have no interest in cease fire to kick can down road

11:30 Ukrainians won’t be strongarmed into accepting a bad deal

12:15 Drones have completely changed complexion of the war

14:00 Russians are targeting civilians, Ukraine hitting energy targets

14:45 Russians don’t care about human losses, just financial losses

16:00 At what point will a bad economy put pressure on Putin?

16:45 Russian elite mysteriously committing suicide or dying

17:30 Prigozhin was  the only person who could challenge Putin

19:00 The Russian regime seems inevitable until the day it falls

20:00 Putin is completely dependent on China

20:45 China will stick with Russia & support war to weaken U.S.

21:45 Putin still has allies in Iran & North Korea

22:15 What does Russia think they’re accomplishing with Poland incursions?

23:30 Russia trying to create divisions between Ukraine and Europeans

24:15 Russia’s actions are only stiffening the European’s spine

25:00 Status of U.S. aid into Ukraine

26:15 What does it look like if the U.S. walks away from Ukraine?

27:30 Russia is still demanding land they haven’t conquered

29:15 Trump wants the optics of a big peace deal where “he wins”

30:30 Trump’s actions with Venezuela look like Putin’s in Ukraine

32:45 Trump’s Venezuela actions undermining international system

33:45 Is Saudi Arabia a dictatorship and what is our relationship with them?

34:30 The Saudi’s primary interest isn’t undermining the U.S. unlike Russia

36:00 Trump’s family has enormous conflicts of interest with the Saudis

37:15 Why security guarantees for Qatar but not Saudi Arabia?

39:15 Trump’s deals in the Gulf seem to benefit him more than U.S.

40:00 Is democracy losing the worldwide fight against autocracy?

42:00 Due to state of U.S. it feels like democratic argument is losing

43:30 Role of silicon valley in fight between democracy & autocracy

44:45 Tech has power to shape opinions and public perception

47:00 Government has never outsourced major tech shift to private sector

48:00 How dangerous is the concentration of corporate power in America?

49:00 The EU is the only entity that could regulate big tech

50:00 Trump’s isolation has been a wake up call to Europe, can it hold?

52:00 Europe was so sure of alliance with U.S. they let things slide

53:00 Level of concern with state of American democracy is very high

54:00 The speed of Trump’s attacks on democracy is unprecedented

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