Inside Russian Intelligence: CIA Insider on Putin’s Playbook, Ukraine & the Next War
What this covers
Former CIA Senior Operations Officer Sean Wiswesser joins State Secrets to break down how Russian intelligence really operates—and why the threat is more serious than most Americans understand.
Drawing on decades of experience targeting Moscow’s intelligence services, Wiswesser explains how Russia blends Cold War tradecraft with modern tools like cyber operations, AI-driven influence campaigns, and hybrid warfare. From election interference to the war in Ukraine, he outlines how the Kremlin is working to weaken the United States and its allies—often below the threshold of open conflict.
The conversation also explores Russia’s relationship with Iran, the evolution of espionage tactics, and why intelligence—not just military force—will define the next global conflict.
If you want to understand how adversaries operate in the gray zone—and what it means for U.S. national security—this is a conversation you don’t want to miss.
00:00 – Intro: Inside Russian Intelligence 01:30 – Russia, Iran, and Strategic Interests 05:30 – How Russian Intelligence Really Works 10:30 – Election Interference & “Active Measures” 16:00 – Cold War Tradecraft vs Modern Tech 20:30 – Ukraine War: Intelligence Failures & Adaptation 26:30 – Why Americans Misunderstand the Threat 31:00 – Is the U.S. Losing the Information War? 34:30 – Final Thoughts: The Next Conflict
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Russian intelligence services operate as state-corporate entities pursuing zero-sum competition against the West through tradecraft rooted in Cold War methods, now amplified by AI and cyber capabilities, with their primary strategic goal being to undermine democratic institutions and prevent the spread of functioning democracies on Russia's borders.
- Russian intelligence services are deeply integrated with military-industrial corruption and profit incentives, making sustained conflict with the West beneficial to their institutional interests
- Active measures campaigns targeting emotional issues in Western democracies aim fundamentally to sow distrust and discord among citizens rather than support specific candidates or parties
- Russia views functioning democracies like Ukraine and the Baltics as existential threats to Putin's regime, explaining the aggressive intelligence and military operations against them
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The fundamental goal of Russian active measures in US elections is to undermine democratic institutions and create internal American discord and distrust by targeting emotionally charged issues, rather than to support specific candidates or parties
“I believe fundamentally the goal of their meddling in our elections is to undermine our entire democracy, Brad. It's to get Americans to do unfortunately what we've done since 2016. Americans fighting with each other. Americans arguing about about disunity and discord and animosity among Americans. That was the goal. That was the fundamental goal of the Russian active measures.”
Russian street-level tradecraft and agent handling methods from the Cold War remain in use today because they are fundamentally superior at avoiding electronic interception compared to digital communications, particularly for high-value penetrations of foreign governments
“when it comes to protecting and handling penetrations of foreign governments, the Russian intelligence services is going to draw back on the tradecraft they used during the Cold War...when we talk about tradecraft, so there's street tradecraft and there's surveillance tradecraft and the Russians tend to fundamentally go back to their Cold War roots”
Russian active measures did not originate with 2016 or the internet but represent continuous KGB operations throughout the Cold War targeting developing nations, Africa, the US, and allies, with their playbook including both paid politicians and unpaid 'useful idiots'
“this is not a new method. I talk about it in the chapter on active measures in the book. Um chapter uh nine of the book. Uh this is a this is a many decades old process. The KGB used throughout the Cold War. They were always trying to influence politics in countries of the developing world and and and countries of in the United States and all of our allies. Africa was a huge battleground.”
Putin considers the dissolution of the Soviet Union the greatest geopolitical disaster of the 20th century, and views Ukraine and the Baltics—which chose independence and democracy—as threats to his regime because he cannot tolerate functioning democracies on Russia's borders
“Putin's big grievance with Ukraine was they don't have a right to exist. Putin commented decades ago, the greatest geopolitical disaster, to his mind, of the 20th century was the dissolution of the Soviet Union”
Russia-Iran relationship is not a strategic partnership with formal frameworks but rather a transactional arrangement where Russia helps Iran only insofar as it damages the United States, driven by Russian intelligence services' zero-sum worldview and profit motives rather than ideological alignment
“this is not a strategic partnership. Okay, these are not formal allies...Russia has none of that with Iran...They're going to help Iran and they're going to interact with Iran uh in terms of this conflict strictly on the terms of what is beneficial to Russian Federation”
The FSB's Fifth Service was specifically tasked with planning the Ukraine war and conducting operational analysis for Putin, but Russian intelligence services fundamentally miscalculated that they could achieve victory in a short war, revealing serious intelligence failure
“The FSB fifth service, it used to be a department, now they call it the fifth service of the FSB. They were in charge of planning the war. They're in charge of operational analysis to the president. They and the Russian intelligence services uh at large really believed they could win in a short war.”
Maskirovka (Russian deception/concealment operations) involves attacking a target, then inventing false explanations for the attack and spreading those explanations through propaganda to blur responsibility
“But you have all this miss maskirovka. The Russians call it maskirovka. They attack and then they look for others to blame. So So you find them amplifying or or inventing explanations like the Venezuelans hacking into voting machines.”
The Baltic states—Estonia, Latvia, Lithuania—have achieved functioning democracies with strong economies and credible militaries within 30 years of Soviet independence, demonstrating a successful model that contradicts Putin's narrative and threatens his regime
“Look at how successful the Baltics are today. Brad, look at the progress they made. My own wife is Lithuanian. I mention that in the book. Look at what they've accomplished. My God, in 30 years, these are fully functioning democracies with outstanding economies that are building militaries to defend themselves and will defend themselves against Russia.”
Many Cipher Brief experts and security professionals at the October threat conference raised the question whether World War III has already started, with significant weight of opinion suggesting the next global conflict will be shaped largely by intelligence operations and gray zone activities
“I heard more talk and dialogue around the question of has World War III already started? And I won't say where the, you know, where the weight on that scale came down on, but many people, including some of your colleagues who regularly contribute for the Cipher Brief, feel that the next global conflict will be largely shaped by intelligence and gray zone activity”
The United States headline the news in Russia every single day, whereas Russia was essentially invisible in US media and policy discourse until 2016, reflecting a profound asymmetry in threat perception and strategic focus between the adversaries
“Conversely, the United States is on the news, headlining the news in Russia every single day. We're always on their news. And a big part of that is in Russian society and there there's a deep-set insecurity with regards to the United States and the West.”
Russian intelligence compartmentation is exceptionally effective, representing one of the few genuine operational strengths that Western counterintelligence must respect, in contrast to other aspects of Russian tradecraft
“I don't like to pay a lot of compliments, but in the book I talk about begrudgingly. Compartmentation is one issue they do well”
Americans have historically been distracted from and gave Russia a strategic pass during the 20-year war in Afghanistan and Iraq, during which time Russian intelligence was actively conducting operations against the West but received minimal attention in US national security discourse
“Americans have been not just distracted is not the right term. We've been engaged. We had 20 years of war, right? Brad, you and I and many of the other Cipher Brief experts, we deployed in the conflict zones...But, in that time period, Russia was getting a pass.”
Peter the Great built St. Petersburg as a window to the West because Russia historically carried deep-seated insecurity regarding Europe and the West, a foundational psychological pattern that continues to drive Russian strategic behavior toward Western democracies
“It's always been there. We can talk another time about going back to Tsarist times. Peter the Great built St. Petersburg as a window to the West because of insecurity over Europe.”
Despite intelligence failures in Ukraine, Russian intelligence services have adapted and evolved remarkably well over the past 2 years, establishing entirely new military units for unmanned systems (drones) and incorporating lessons from the conflict into operational improvements
“We also have to recognize they're a formidable opponent. They've adapted remarkably well, just as the Ukrainians have. The Russian intelligence services and the Russian military have adapted remarkably well in the past 2 years in particular. Russians have stood up an entire new part of their military called unmanned systems troops, the drones.”
No voting machines were actually compromised in 2016 US elections; this was confirmed by former Attorney General Barr, but Russian maskirovka (active measures) succeeded in creating doubt about election integrity by inventing false explanations like Venezuelan hacking
“No voting machines were compromised. Former Attorney General Barr, who was appointed by Trump in the first administration, he stated this. He said it's Okay, they looked at it. There were no voting machines compromised. The states are in charge of their individual elections and those machines weren't compromised. It wasn't that foreign actors didn't try. But you have all this miss maskirovka.”
Rick Ames (CIA spy) and Robert Hanssen (FBI spy) used Cold War tradecraft methods including dead drops and signal sites when passing classified information to Soviet handlers
“If you look at the penetrations of the US government, uh Rick Ames from CIA, Robert Hanssen, they used that same tradecraft. Dead drops, signal sites.”
Yeltsin and Gorbachev allowed the Soviet republics to choose their own path after Soviet dissolution, making subsequent Russian aggression against post-Soviet states an act of will rather than response to NATO expansion
“Don't mind the fact that these people all went their way because they wanted to. And Yeltsin, for all the mistakes Yeltsin made, Gorbachev before him, thank God they said, You know what? We're going to let the republics of the Soviet Union decide.”
Russian intelligence services (FSB, GRU, SVR) function as corporations integrated with defense sector conglomerates and profit from state corruption and kleptocracy, making prolonged conflict in Ukraine economically beneficial to these services and their associated military-industrial networks
“in the case of the Russian intelligence services, these are corporations, Brad. These aren't just services...the FSB, the GRU, the SVR, they are tied in with huge conglomerates and interests in the defense sector...being at war in Ukraine is in the interest of the FSB, the GRU, the SVR. They're making money off of it”
What has fundamentally changed in Russian active measures over recent decades is not the strategy but the technological capability: the transition from human troll farms and paid writers to AI-generated content means they can now reach populations at an unprecedented scale, with approximately 50% of social media content on targeted issues potentially being AI-generated disinformation
“what's changed fundamentally over the decades in the recent decade in particular, it's the ability to use cyber warfare...the ability to use social trolls to use trolls, troll farms in Russia on social media. And now the ability to use cog AI, you don't even need people doing it. You just write the program, I want you to go attack this issue, argue both sides of the debate. Upwards of 50% of the content they're saying now on social media is is is potentially is is AI.”
There is a critical distinction between high-value government penetrations (handled with elite tradecraft) and lower-level agents recruited for one-time or limited use in hybrid warfare operations, which use different operational security standards
“There's a huge difference between a hacker or some teenager that they recruit and they pay $10,000 to go take pictures of a rail line or God forbid even go carry out an attack, an explosion...And a penetration of a foreign government. In the case of a penetration of a foreign government, they're going to use the highest levels of their tradecraft”
The US is the 'glassiest of glass houses' compared to closed autocratic societies like Russia and China because as a free democracy with open systems, the US is far more vulnerable to intelligence targeting, and cannot reciprocate against adversaries in ways they use against America
“someone mentioned sort of the disparity of America as a target versus like Russia or China as a target, a closed-off autocratic society. And they were simply talking about the cyber uh tools and techniques. And they said that America is the glassiest of glass houses, meaning our target our threat sort of landscape is so wide open because we're a free and democratic society, and we're just not able to, even if we wanted to reciprocate against our adversaries in ways that they do for us”
America cannot afford strategic isolationism regarding Ukraine and Taiwan because Russia and China are actively competing for 21st-century dominance, and the American century of the 20th century was defined by being a symbol of freedom that others aspired to
“we can't afford to sit out Ukraine. We can't afford to sit out Taiwan. America is under attack. America is under attack in hybrid war now and we will be in the future. Russia and China are trying to vie for the title of the 21st century. The American century, the 20th century was known of because we were a symbol of freedom for the world to aspire to.”
Russians believe they are already fighting NATO and the West in Ukraine, a belief the speaker characterizes as a propagandized version despite being factually false—Russia initiated the invasion unprovoked
“Their propaganda propagandized version of that war is of course that they're already fighting NATO and they're fighting the the West. Russia frames it as preventative war. We all know that's nonsense. They attacked Ukraine.”
American politicization at senior intelligence levels has damaged public trust in the intelligence community, though the vast majority of intelligence workers operate apolitically and are not part of any 'deep state' conspiracy—rebuilding this trust is essential for countering Russian threat perception
“politicization at the senior levels has led to distrust. And that we need to rebuild. I'm a firm believer...We cannot have a politicized leadership, nor intelligence community or at large. I don't believe we have at the root level. I don't believe any nonsense about a deep state conspiracy. We know that that tens of thousands, hundreds of thousands of Americans are trying to serve their country in the intelligence community.”
George Tenet set a positive example by remaining quiet after leaving the CIA directorship, avoiding the public limelight, modeling restraint—contemporary former intelligence officials who engage in partisan politics damage institutional credibility and should follow Tenet's example
“I love George Tenet because when he left CIA, and he was a great director, he mostly stayed out of the into the shadows and he stayed out of public limelight. He said, 'You know, I did my part. I loved being director of CIA.' Hey, we need to get back to the We really do because currently we're in an atmosphere of just toxicity right now, where there's that distrust.”
The intelligence community maintains apolitical professional culture at grassroots level despite senior leadership politicization, with no observation of partisan considerations affecting operational decisions during Westwester's 28-year career
“I believe the good news for the American people is you still have a You know, you still have the vast majority of Americans working in the intelligence community...I never heard anybody talk about my entire 28-year career in the intelligence community, Brad, I never had anybody ask me at work, 'Hang on a second, before we do that, is that going to benefit them Dems or Republicans?' Never. Not once.”
Some European leaders and politicians are currently operating as 'useful idiots' for Russia by advancing Russian interests without payment because they are ideologically sympathetic
“There's certainly some leaders and politicians who are doing Russia's will and they're doing it for free. I don't believe that they're paid off cuz they don't need to be.”
The Ukraine conflict is underutilized as a source of lessons learned that could inform US and Western strategy; Ukraine should be systematically mined for strategic insights about hybrid warfare, conflict adaptation, and democratic resilience against authoritarian aggression
“I've also written a piece, Echoes of 1940, that piece I wrote for you all Cipher Brief. I hope your your listeners will go check it out. I talked about we should be mining Ukraine. I said this back in December. Why are we not mining them for more lessons learned?”
Winston Churchill's 1940 message to occupied Europeans—'The dawn will come...Brightly will it shine upon all who suffered for the cause'—is relevant to contemporary Ukraine conflict, with the implication that America must support Ukraine as the arsenal of democracy just as it supported Europe in WWII
“I quoted in that article Winston Churchill. It's really important words that he said to the people occupied in Europe in 1940. You know, the dawn will come. Brightly will it shine upon all who suffered for the cause. That historical dawn, when it comes, we want everybody to say America did their part. We're the arsenal of democracy.”
Russian intelligence services will never be held accountable for their role in planning and miscalculating the Ukraine war because accountability depends on regime change—Putin supports the services, they serve as his Praetorian Guard, and as Putin goes, so go the intelligence services
“the Russian intelligence services are not going to have any accountability for this war in Russia, not under this regime, under Putin. As Putin goes, so goes the Russian intelligence services. So, he supports them. They're his Praetorian Guard.”
Kevin Relay and other respected academics argue against using the term 'expendable agents' because it misrepresents Russian tradecraft—no agents are truly expendable to Russian intelligence services, though some are recruited for limited-use operations
“some people have used the term uh expendable agents. I don't agree with that term. Kevin Relay is a very well-respected uh academic and former officer himself writes on it. He said we shouldn't use the term. No agents are truly expendable to the Russians or any intelligence service.”
The book has been endorsed by former senior CIA leaders including two former Deputy Directors (Mike Sulick as forward-writer, Jennifer Eubank), suggesting it represents credible institutional knowledge
“I'm fortunate to have the endorsement of a lot of former senior senior leaders at CIA including two former deputy directors. Uh DDO Mike Sulick wrote the forward to the book. He thought it was very unique. Our DDI Jennifer Eubank is very gracious with her endorsement of the book, too.”
Thomas Rid's book 'Active Measures' discusses cyber warfare, social media troll farms, and the evolution of Russian active measures from Cold War tactics to modern operations
“Thomas Rid wrote a great book called Active Measures. Where Rid talks about cyber warfare, the ability to use social trolls to use trolls, troll farms in Russia on social media.”
Mark Kelton and other Cipher Brief experts have written about the danger of politicization in intelligence leadership, a concern the speaker agrees with firmly
“Some of your other Cipher Brief experts, Mark Kelton, has written about the danger of politicization. And I firmly agree with him.”
The Senate Select Committee on Intelligence (SSCI) and Director of National Intelligence reports documented Russian election meddling in 2016, with senator Marco Rubio endorsing the SSCI findings as factual
“The Senate Bipartisan Report, SSCI Committee Report that went out, Marco Rubio was a senator, he was a member of that committee, he endorsed it. And the DNI Report, which I cite on my chapter chapter on active measures.”
Glavny protivnik (Russian: главный противник) is the Russian term meaning 'main adversary,' which is how Russian intelligence services refer to the United States in their strategic doctrine.
“Remember, the United States is what the Russians call the glavny protivnik. We're the main adversary.”
Westwester spent his CIA career as a 'denied area expert' in the Directorate of Operations, focusing on Russian intelligence as an adversary and recruiting/handling spies
“the book came out of course my career and I was known as a denied area expert. CIA let me share that in the book. I was in our senior expert cadre in CIA in the Directorate of Operations when I retired. Um the bulk of my career was focused on the Russian intelligence services, Russian Federation more broadly as an adversary of the United States and collecting intelligence, recruiting, handling spies.”
The book focuses on tradecraft specifics—how Russian intelligence operationally carries out espionage, surveillance, and special operations—rather than being a personal memoir, and is written with modesty as confirmed by Ed Lucas's review
“The book is not a memoir. There's no self-aggrandizement in it. One of the one of the highest pieces of praise recently, Ed Lucas, a senior former senior editor with The Economist, wrote a very generous review in which he stated, you know, this book's written modestly. That's the highest compliment I could be paid”
The author's wife is Lithuanian, providing personal connection to and testimony about Baltic success and independence, suggesting family-level validation of democratic development in post-Soviet states
“My own wife is Lithuanian. I mention that in the book”