On the second day of Russia’s invasion of Ukraine, one of President Vladimir V. Putin’s closest aides refused to follow his orders.
Mr. Putin had told the aide, Dmitri N. Kozak, to demand Ukraine’s surrender, according to three people close to Mr. Kozak. Mr. Kozak declined, insisting that he did not know what the Russian leader was trying to accomplish with his invasion. As the call grew heated, Mr. Kozak told Mr. Putin that he was ready to be arrested or shot for his refusal.
Only later did Mr. Kozak learn that Mr. Putin had put that call in 2022 on speakerphone, the people said, turning the senior officials in the president’s office into witnesses to a rare moment of insubordination.
Mr. Kozak was a lone voice of dissent in Mr. Putin’s inner circle, a small crack in his iron grip on power. With so few people willing to challenge him, Mr. Putin has exerted near-total control over Russia’s prosecution of the war. It’s partly why, almost four years later, the Russian leader is able to stick to his hard-line demands even as pressure mounts for a cease-fire.
Mr. Kozak, 67, resigned as a deputy chief of staff to Mr. Putin this September, a month after The New York Times reported on his private criticism of the war. In interviews since then, six Russians close to Mr. Kozak described the transformation of a 30-year Putin confidant into a locus of antiwar sentiment in the Russian elite. Most spoke on condition of anonymity, given the danger of retribution for discussing confidential Kremlin politics.
In making his disagreements with the president known within the ruling elite, Mr. Kozak is giving voice to quiet dissatisfaction felt by many in Moscow’s business and cultural class, and even by other government officials, the six confidants say. This year, that dismay has been exacerbated by Mr. Putin’s refusal to end the war even on the favorable terms being offered by President Trump.
“Dmitri Nikolayevich is gone, but the mood is the same,” said Aleksei A. Venediktov, a prominent Moscow-based journalist who knows past and present Kremlin officials, including Mr. Kozak. “He is important as a marker.”
Mr. Kozak, the most senior government figure to have broken with the president over the war, remains based in Moscow. He first worked with Mr. Putin in the 1990s, when both were senior officials in the St. Petersburg mayor’s office, and appears to believe their personal ties provide him some measure of safety, the people who know him said.
Mr. Kozak has not gone public with his criticisms. An acquaintance of his, the political analyst Arkady Dubnov, said that Mr. Kozak declined to be interviewed for this article.
But Mr. Dubnov said events since the invasion on Feb. 24, 2022, have only reinforced Mr. Kozak’s views. “His assessments, expressed to Putin on the eve of the start of military action, have been borne out with terrifying accuracy,” said Mr. Dubnov, who lives in Israel.
Inner Circle
Mr. Kozak’s hands shook as he stepped to the lectern. He explained, mumbling at times, why negotiations with Ukraine were going nowhere. He added that he had more to say, but Mr. Putin cut him off.
“I suppose we’ll talk about it separately,” Mr. Kozak said.
It was Feb. 21, 2022. At a televised Security Council meeting in a colonnaded Kremlin hall, Russia’s top officials lined up behind Mr. Putin’s looming invasion.
Mr. Kozak did not play along.
He had known Mr. Putin longer than just about anyone else in the room. He had managed Mr. Putin’s first re-election campaign, taken charge of preparations for the 2014 Winter Olympics and overseen the integration of annexed Crimea into Russia.
In early 2022 before the invasion, Mr. Kozak was negotiating with Ukraine over the proxy war in the country’s east. He held an eight-hour session in Paris that January, talks that Ukraine said sent a “very positive signal.” Several former Ukrainian and U.S. officials familiar with those talks said they believed that Mr. Kozak was genuinely pursuing a diplomatic solution rather than stalling for time as Russia prepared its invasion.
As Mr. Putin massed troops, Mr. Kozak drafted a lengthy memo laying out the likely negative consequences of a war, his confidants say. According to one person who saw it, the memo warned of the possibility that Sweden and Finland would join NATO — a prediction that would prove prescient.
On Feb. 21, Mr. Kozak addressed the Security Council again in a part of the meeting that was not televised, according to several people close to him. Ukrainians will resist, Mr. Kozak said. Sanctions will be severe. Russia’s geopolitical position will suffer.
Mr. Putin then told all officials except Mr. Kozak and the permanent members of the Security Council to leave the room, according to the people close to Mr. Kozak. He asked Mr. Kozak to restate his arguments. Then Mr. Putin dismissed everyone else, except for Mr. Kozak, who was still standing at the lectern.
They were now alone under the vaulted ceiling of the Kremlin’s Hall of Saint Catherine, roughly 30 feet between them.
What is it? Mr. Putin asked Mr. Kozak, according to two people close to Mr. Kozak. Why are you against it?
Mr. Kozak, according to the people, did not budge. It was the last time the two men spoke before Russia started bombing Kyiv in the early morning of Feb. 24.
Refusing an Order
Some news outlets have reported that Mr. Kozak called Andriy Yermak, then the chief of staff to President Volodymyr Zelensky of Ukraine, in the hours after the invasion and demanded that Kyiv surrender.
Mr. Kozak has insisted to several associates that the story is false. Instead, he told them, it was Mr. Yermak who called him that day. Mr. Kozak said he wanted to work toward a negotiated peace as fast as possible, those people said.
By the second day of the invasion, Mr. Kozak was negotiating a possible cease-fire deal with Davyd Arakhamia, another Zelensky aide, according to three people close to Mr. Kozak. The deal would have involved Russia’s guaranteeing Ukraine’s security and withdrawing from all parts of Ukraine except Crimea and the eastern region known as the Donbas.
The negotiations infuriated Mr. Putin.
The evening of Feb. 25, Mr. Kozak briefed Mr. Putin via the Kremlin’s secure phone system, according to the three people.
Mr. Putin assailed Mr. Kozak for exceeding his mandate by discussing territorial issues, and told Mr. Kozak to inform Kyiv that Russia would only negotiate Ukraine’s surrender. To Mr. Kozak, Mr. Putin appeared to be sharply shifting his negotiating position. He said he could not negotiate if he did not know Russia’s end goals.
Mr. Putin brushed those concerns aside and ordered Mr. Kozak to negotiate as instructed. Mr. Kozak refused. It was on this call that Mr. Kozak told Mr. Putin that he was ready to be arrested or shot for his refusal, the people said.
By the end of that tense call with Mr. Putin, Mr. Kozak did agree to inform Ukraine about Russia’s demand for surrender. He called Mr. Arakhamia, with Mr. Putin silently listening in. Mr. Arakhamia refused.
The next day, Feb. 26, Mr. Putin’s position appeared to shift a second time, according to the three people. In the morning, Mr. Putin’s first deputy chief of staff, Sergei V. Kiriyenko, called and told Mr. Kozak that another Kremlin aide, Vladimir R. Medinsky, would now be heading Russian negotiations with Ukraine.
Late that evening, Mr. Medinsky and Roman Abramovich, a Russian billionaire, arrived at Mr. Kozak’s home. They told him they were going to Belarus to negotiate with Ukraine under a new mandate from Mr. Putin: to discuss security guarantees, but not Ukraine’s borders.
Representatives for Mr. Yermak, Mr. Arakhamia and Mr. Abramovich did not respond to requests for comment. The Kremlin also did not respond.
Challenging the System
Mr. Kozak would never regain his formal role dealing with Ukraine. He lost power to Mr. Kiriyenko, who this year took over Mr. Kozak’s portfolio of managing relationships with other former Soviet countries.
But he did not lose his job. He kept his office in the Soviet-era Presidential Administration building a few blocks from the Kremlin, where he met with back-channel emissaries from the West, according to several people with knowledge of the events. He chain-smoked cigarettes as they brainstormed possible peace plans. He told them that he maintained access to Mr. Putin, signaling that the Russian president was aware of those secret conversations.
At one point, the president suggested to Mr. Kozak that he make proposals to improve Russia’s economic climate. Several confidants who saw Mr. Kozak’s memo in response said they were stunned by it.
The memo, they said, proposed that Mr. Putin stop the war, negotiate with Ukraine, and make liberalizing domestic reforms. Mr. Kozak proposed that the Russian judiciary be made independent of the de facto oversight of law enforcement agencies — a near-heretical idea because of the status of Russia’s security services as its most powerful forces.
Some of Mr. Kozak’s confidants said they were surprised not only by the proposals, but also that he was sharing them outside the Kremlin, given the veil of secrecy that usually surrounds Mr. Putin. They said that Mr. Kozak seemed to be concerned about his legacy and trying to separate himself from Mr. Putin.
Konstantin F. Zatulin, a member of parliament in Mr. Putin’s United Russia party who knows Mr. Kozak, described him as remaining loyal to Mr. Putin. But he said Mr. Kozak was the rare Kremlin aide who “didn’t hide his opinion.”
“In the presidential administration, it is not customary to argue much with the opinion of your superior,” Mr. Zatulin said.
A Muddled Legacy
Mr. Dubnov, the acquaintance of Mr. Kozak’s in Israel, said that Mr. Kozak believed “he was working in the service of the state, and not in Putin’s personal interests.” Their breakdown in relations, Mr. Dubnov said, came after Mr. Kozak, with the invasion, “discovered that for Putin there are no red lines that he is not prepared to cross.”
“The price that the country is paying for the great-power ambitions of its leader became unacceptable” for Mr. Kozak, Mr. Dubnov said.
Like many Russian elites, Mr. Kozak continues to display loyalty to Mr. Putin by refraining from any public criticism. And Mr. Putin has also telegraphed some loyalty to him.
Mr. Kozak traveled repeatedly to Israel for medical treatment, as well as to Turkey and the United Arab Emirates. It was a sign of Mr. Putin’s continued trust, given the limits he placed on wartime travel by government officials.
In September, Mr. Putin accepted Mr. Kozak’s resignation — especially notable since Mr. Putin prefers to ensure senior officials stay loyal by appointing them to sinecures rather than letting them leave government service.
Mr. Kozak’s legacy remains bound up with Mr. Putin’s.
A liberal member of the St. Petersburg Legislative Assembly in the 1990s, Leonid P. Romankov, remembers Mr. Kozak as a “professional” who, unlike many other city officials, strove to follow “the letter of the law.” But he became disenchanted with Mr. Kozak as he stood by while Mr. Putin dismantled Russian democracy.
“He took the path of conformity,” Mr. Romankov said. “He could have understood much earlier where everything was heading.”
Paul Sonne contributed reporting.
Anton Troianovski writes about American foreign policy and national security for The Times from Washington. He was previously a foreign correspondent based in Moscow and Berlin.
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