When Rob Dannenberg arrived in Moscow in the late 1990s to take on a senior role with the CIA, the Russian capital was a wild and dangerous place.
With the post-Soviet state crumbling under the drunken presidency of Boris Yeltsin, armed gangsters and Chechen terrorists posed deadly risks. So too did the unruly security services trying to tackle them. “There were roadblocks set up around town, where the street militia were quite capable of being violent if it suited them,” Dannenberg recalls.
Adding to the chaos were disgruntled Russian intelligence officers, upset at their beloved KGB being dissolved. Within its replacement, the FSB, certain elements “weren’t under complete control,” Dannenberg explains. They were “capable of undertaking actions” without seeking permission from the Kremlin.
“There were plenty of Russians who held a deep grudge, and still do to this day, about the collapse of the Soviet Union,” he says.
One of them, was Vladimir Putin.
Dannenberg remembers meeting the former KGB colonel during the first of his two stints in Moscow, in the mid-1990s. He shook hands with Putin, who was merely a government official at the time, during a reception at the US Ambassador’s residence.
During his time in Moscow, Rob Dannenberg also visited the statue of Soviet spy Richard Sorge and stood outside the Kremlin in Red Square (Photos: Rob Dannenberg)Dannenberg returned for a second spell in the early 2000s when the CIA promoted him to Moscow station chief – the top US spy in Russia. He had “full access” to every piece of intelligence on the country sourced by the agency’s officers.
By then, Putin was president.
“Those of us who served in Moscow understood Putin maybe a little bit better early on than others did,” says the CIA veteran, speaking to The i Paper from his home in Colorado. When the Russian dictator annexed Crimea and occupied eastern Ukraine in 2014, then launched his full-scale war in 2022, “none of us were surprised”.
From the very start, Putin’s political ethos was about restoring state control, rebuilding the military and achieving mastery over other former Soviet republics. “Ukraine is the single most important element in that still unfulfilled part of Putin’s vision,” says Dannenberg.
“I dealt with the KGB my entire life,” he adds. “I understand how this guy thinks.”
Vladimir Putin, seen bottom left while wrestling at school, succeeded Boris Yeltsin, right, as Russian president (Photos: Getty)It’s his knowledge of how Russian spies are trained to deceive and control people, sometimes without their victims realising, that makes him so concerned whenever he hears about Putin’s latest talks with Donald Trump.
“Putin looks at Trump and sees a weak guy, vain, with huge ego,” says Dannenberg. He admits Trump is hardly the first US leader to have a big opinion of himself, but fears the current US president is “incredibly naive” and vulnerable to the Kremlin’s influence, as Putin seeks to further divide the US and Europe.
Indeed, when Trump met with Volodymyr Zelensky for vital talks in Florida on Sunday night, it turned out that the US President had called Putin in advance. In a following press conference, Zelensky could scarcely contain his bewilderment when Trump declared that Putin “wants Ukraine to succeed”.
And when Putin later claimed, with no evidence, that a Ukrainian drone had been aimed at his residence – which Kyiv has denied – Trump seemed to suggest he was wise not to provide Zelensky with Tomahawk cruise missiles.
For critics like Dannenberg, these were just the latest examples of the American leader parroting what his Russian counterpart has told him.
“He’s being manipulated, in the way that a good case officer like Putin would manipulate this guy. He’s not monogamous, he’s greedy, he’s fascinated by gold – all these are things that, if I were a case officer, I would be leveraging to get this guy to do what I want him to do.
“When that happens to align with Trump’s ambition to get a Nobel Peace Prize, so much the easier, right? You’re pushing on an open door.”
Volodymyr Zelensky was surprised when Donald Trump said Russia ‘wants Ukraine to succeed’ (Photo: Joe Raedle/Getty)How Putin is taking advantage of ‘Trump’s greed’
As Moscow station chief, Dannenberg’s primary role was to set “whatever tactics officers needed to conduct our operations without being compromised by hostile surveillance or double agents”.
Although he retired from the CIA in 2007, he can’t help despairing about the “real inflection point” facing the Western world as we enter 2026.
“It centres around the success or failure of Putin’s invasion of Ukraine. But we’re dealing with a US administration that fails to understand the strategic importance of Ukraine.” He argues that Trump’s priority is winning business opportunities, not the war.
To secure continued support from Trump, Ukraine gave the US a share of valuable mineral deposits. Now, Dannenberg believes Putin is using potential investment opportunities in Russia – if the war ends and sanctions are lifted – to tempt the White House into siding with the Kremlin on key matters.
This would explain Trump’s oscillating views. “It’s been like a yo-yo – first we’re behind Ukraine, then we’re cutting off support. It’s just been crazy.”
After the Cold War, Dannenberg visited the Berlin Wall and the city’s ‘Bridge of Spies’ in Glienicke (Photos: Rob Dannenberg)Just as Trump’s key negotiator, Steve Witkoff, is a property tycoon with no previous experience of diplomacy, Putin’s envoy, financier Kirill Dmitriev, is head of the Russian Direct Investment Fund. This is no coincidence, says Dannenberg, calling Witkoff “a fool”.
Dmitriev will be “dangling in front of Witkoff fantastic real-estate concessions” in Russia, trying to play on “Trump’s greed”, he says. Perhaps the US president hopes there will be “a Trump Hotel on Red Square” if peace is secured.
But many Americans have been burned after trying to do business in Russia, where the regime has a record of seizing property and reneging on deals. “The wreckage of those individuals’ enterprises is still smoking, and Trump won’t be any different… When he’s no longer president, I guarantee you that hotel’s gone, and all the money will be gone. The Russians will be perfectly happy to arrest Trump’s business representatives and throw them in the clinker.”
The Wall Street Journal recently reported that Russia made diplomatic overtures to Witkoff, encouraging the US President to send him into talks – without CIA advisers – instead of Ukraine-aligned colleagues, after Putin had been “studying psychological profiles of the officials around Trump“. However, the White House insisted there was no foreign influence in his appointment and that Witkoff is doing an “incredible job”.
Its press team did not provide a response to any of Dannenberg’s views.
Russia’s negotiator Kirill Dmitriev and the US envoy Steve Witkoff are both businessmen (Photo: Vyacheslav Prokofyev/AFP via Getty)Dannenberg acknowledges that Trump’s abrasive tactics succeeded in forcing Nato’s European members to begin investing more in defence, after relying on American taxpayers for too long. Perhaps Trump, who claims a peace deal is “95 per cent done“, will surprise his opponents as his tougher sanctions hit Russia’s economy.
He also admits that the US had let Ukraine down long before Trump took office last year – with Barack Obama doing “basically nothing” to counter the partial invasion in 2014, and Biden being “slow” to provide military support in 2022.
Trump wants to shape his place in history, but if he is not careful, Dannenberg warns, he could resemble the prime minister who tried appeasing Adolf Hitler. “His legacy might be like Neville Chamberlain.”
During his CIA work, he never saw evidence that Trump was a KGB asset, as some former Soviet agents have claimed. He believes that if this were true, proof would have emerged during Joe Biden’s presidency, given the Democratic desperation to prevent a Trump election victory.
But Trump doesn’t need to have been recruited or blackmailed by the KGB to be useful to the Kremlin, says Dannenberg, because he’s so easily influenced by wealth and power.
Dannenberg visited Ukraine in May (Photos: Rob Dannenberg/Kyiv Security Forum)‘Putin is not as strong as he presents himself’
After leaving the CIA, Dannenberg served as a security adviser for BP and Goldman Sachs, and now enjoys an outdoor life in the Rocky Mountains. He’s recently published an espionage-themed cocktail guide, A Spy Walked Into A Bar, partly inspired by the drinks in Ian Fleming’s James Bond novels.
He still serves as a consultant, however, and visisted Kyiv last spring to meet with Ukrainian officials.
What frustrates Dannenberg most is that he firmly believes Putin’s regime could fall apart if the White House strengthened its support for Zelensky. He says even if Ukraine can’t expect to advance into Russian-held territory any time soon, its forces still have faith that they can inflict enough casualties to “bring the Russian army to a standstill”.
He highlights how the USSR collapsed partly because of its failed invasion of Afghanistan, in which 15,000 Soviet troops died. That number is small compared to the “staggering” 250,000 Russians estimated to have died in Ukraine so far.
“It’s like what happened in the First World War,” says Dannenberg. “They would return to Moscow, there would be regime change and we win.”
“Putin is not as strong as he presents himself,” he adds. “Russia is a pariah state in much of the world.” Its invasion convinced neighbours Sweden and Finland to join Nato, while allies have been toppled in Syria and weakened in Iran.
Donald Trump met Vladimir Putin in Alaska in August (Photo: Andrew Caballero-Reynolds/AFP via Getty)Ukraine has recently used British Storm Shadow cruise missiles to hit oil facilities in Russia. But after Trump’s comments this week, it seems less likely than ever that the US will supply Ukraine with Tomahawks. Dannenberg says this is a mistake.
“We need to take the fight to the Russian Federation. The Russian state-controlled media have done a really effective job of hiding the war from the average Russian. We need to make the war visible to them, hence strikes at targets deep inside.” These have caused fuel shortages in “big swathes” of the country he says.
Russian officials are said to be concerned about stagflation and a potential banking crisis in 2026, after a sharp drop in oil and gas income as a result of sanctions.
“The economic problems that Russia faces are real… You wonder at what point Russian elites themselves will say: ‘This guy’s taking us down a bad road, we’ve got to manage this situation better or we’re really going to lose’.”
The CIA veteran fears Trump will “put pressure on Ukraine to surrender”. He advocates the alternative: “Put maximum pressure on the Russian Federation, to try to get the Russians to effect regime change… Maybe that prevents the next war.”
Dannenberg is the author of a spy-themed cocktail guide (Photos: Rob Dannenberg)He is disturbed at how Putin is already “unsettling European populations, to make them feel at risk”, using hybrid warfare. He points to recent closures of major European airports because of dangers caused by suspected drone activity. “Imagine if that was Heathrow or Gatwick.”
Simply investing in protections is not enough, says Dannenberg. “He’ll just throw more drones at you.” Nato must find an effective way of fighting back, because otherwise “Putin is not going to stop.”
He discounts the possibility of Putin using nuclear weapons in Ukraine, however. Mainly because his key ally Xi Jinping will have ruled this out. The last thing China wants is for its rivals Japan and South Korea to be frightened into becoming nuclear powers themselves. But he believes weaknesses in Russia’s military technology, exposed in Ukraine, might also dissuade Putin.
“He might push a button and things might not go boom.”
For all this bullishness, however, Dannenberg still fears the worst under Trump. “Russia could potentially win – and there would be consequences of that for all of us.”
@robhastings.bsky.social
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