📚The TL;DR📝

1. Dmitry Kozak: Former Deputy Chief of Staff of the Presidential Executive Office of the Russian Federation. Born December 7th, 1958 in Bandurove, Ukraine. 

2. Kozak began his public service career alongside Vladimir Putin in Saint Petersburg Mayor Anatoly Sobchak’s office, before joining Putin in Moscow, where he quickly became an important fixer.

3. Kozak was responsible for managing some of Putin’s most challenging crises: the 2014 Winter Olympics, relations with Moldova, and the Minsk Accords in the Donbass.

4. When the war in Ukraine began, Kozak emerged as one of the few powerful voices opposing the conflict, and he gradually became a marginal figure in Putin’s circle.

5. Kozak’s resignation comes at the same time as a dramatic Russian escalation in Eastern Europe, suggesting Putin plans to continue the conflict for the long haul.

📌The Rise and Fall of the “Cheshire Cat,” Dmitry Kozak📌

The war in Ukraine almost never happened. On the eve of the invasion, Dmitry Kozak, the Deputy Chief of Staff to Vladimir Putin’s presidential administration, drew up a comprehensive agreement with the Ukrainian government. Putin would have gotten everything he wanted: Ukrainian state neutrality, and the Donbass and Crimea would remain under Russian occupation. Putin ignored it and invaded anyways. Kozak would stay on for another three years.

Nevertheless, Kozak resigned on September 18th. The only public insight into his resignation comes from the Russian business newspaper, RozBiznessConsulting, which reported that Kozak was weighing an offer to join the private sector. This dry headline obscures the significance of Kozak and his resignation. Kozak is one of Vladimir Putin’s longest-serving aides, a man who followed Putin from the Saint Petersburg city hall to the heights of the Russian presidency.

Along the way, Kozak became one of Putin’s most important fixers; when Putin faced international embarrassment, he could count on Kozak to straighten out the situation. His wry smile, dry humor, and scheming nature led both Kremlin insiders and Western reporters to dub him the “Cheshire cat,” and he was a ubiquitous presence in Russia’s major foreign and domestic policy initiatives.

Despite his prominence, Kozak opposed the most significant move of Putin’s time in office: the full-scale invasion of Ukraine launched in 2022. Kozak’s faith in diplomacy alienated him from the rest of the Kremlin. He was the last powerful dove remaining in Putin’s orbit, and his departure comes as Putin has fursther escalated the war, violating NATO airspace with drones and fighter jets. These provocations suggest Putin intends to continue, if not escalate the war, and that he will not tolerate any further dissent.

The Cheshire Cat’s Cradle

Kozak’s early life is shrouded in mystery. He was born to an ethnic Ukrainian family in the small village of Bandurove in central Ukraine, and after finishing school, was conscripted into the Soviet army, where he served in the elite Spetsnaz unit attached to the Military Intelligence Directorate. Little is known about this service; until 2006, the Russian government described him merely as a “paratrooper” during his conscript service. He briefly attended a technical school in Ukraine before transferring to the elite Faculty of Law at Leningrad State University (LGU) in 1985.

Kozak blossomed at LGU. He excelled in his classes and joined the circle of students around Anatoly Sobchak, a gifted legal scholar and past mentor to Vladimir Putin. After graduating with a “red diploma,” the highest academic grade in the Soviet educational system, he won a plum position in the Leningrad Prosecutor’s Office, where he was rapidly promoted, becoming a senior prosecutor in 1989, an extraordinary achievement just four years after his graduation. 

This could have been the unremarkable end to a bland story about a bright young Soviet bureaucrat, but, come 1989, the Soviet Union was collapsing. His mentor, Sobchak, had just been elected as an independent deputy in the first open elections to the Soviet Congress of People’s Deputies, the Berlin Wall had fallen, and the Soviet protest movement burst into the open. Kozak, a gifted opportunist, moved to the private sector, where he briefly worked as a lawyer for the new private-sector businesses emerging in Leningrad. 

In 1990, a new opportunity arose for Kozak. Anatoly Sobchak launched a campaign to restore Leningrad's original name, Saint Petersburg, and ran for mayor. He won both elections and began recruiting his old students to his mayoral administration. Putin became Sobchak’s advisor for international affairs and then his external relations director, and Kozak became his chief counsel, managing the complex legal affairs of Saint Petersburg. Several other future Putin allies, including his eventual Prime Minister and one-time successor, Dmitry Medvedev, worked alongside Putin under Sobchak. Kozak was known as a demanding and precise manager; his main task was to de-Sovietize the Saint Petersburg municipal codes.

In 1996, Sobchak’s re-election bid failed, but Kozak stayed on to complete his work in the new government, while Putin went to Moscow and quickly rose through the ranks of Boris Yeltsin's incumbent administration. In 1999, Yeltsin appointed Putin his prime minister and effectively his heir apparent. Putin then brought Kozak on as his chief of staff. When Yeltsin resigned after military defeat in Chechnya at the end of 1999, Putin ascended to the presidency and considered Kozak for the all-powerful Prosecutor General role, which would have made Kozak Russia’s most important legal official.

Enemies within the Kremlin got the better of him. Dmitry Medvedev, a former fellow student at LGU, blocked his appointment, and Kozak was reduced to Deputy Head of the Presidential Administration. This loosely defined position allowed Putin to dispatch Kozak where needed. In his new role, Kozak became the manager of Putin’s campaign to streamline the Russian bureaucracy and the representative to Russia’s Southern Federal District. This vast territory includes the volatile North Caucasus region. He did not thrive in the position, finding himself at odds with the Kadryov family in Chechnya and the Federal Security Service (FSB) generals managing Russia’s counterinsurgent war. 

Saving Sochi and Managing Minsk

Kozak’s first years in the presidential administration were otherwise unremarkable. He failed to broker a peace settlement between Moldova and the pro-Russian rebels in Pridnestrovie. Nevertheless, rumors swirled that Putin seriously considered appointing Kozak to the Prime Minister’s office and backing him for president in 2008. Kozak hesitated, and the position instead went to Dmitry Medvedev. Kozak seemed poised to fade into the background of Putin’s administration, another faceless and nameless figure partially responsible for his consolidation of power.

The 2014 Winter Olympics gave Kozak a new lease on political life. Putin intended for the games to showcase the newfound prosperity and stability of Russia. By 2013, however, the games had spiraled into an embarrassing boondoggle. Sochi, where the Winter Olympics were set to be held, is a warm resort city in the southwest of the country, with a mild climate influenced by the Black Sea. There was no guarantee of enough snow for the skiers and snowboarders. Construction was moving slowly and running trillions of rubles over budget. The State Prosecutor’s office opened investigations into contractors for embezzlement. A new wave of terrorism from Chechen militants threatened to keep tourists away. Putin needed a loyal and able aide to rescue the project, and found Kozak to be the man for the job.

Kozak’s management turned the games from a disaster in the making to a propaganda victory. There were no terror attacks in Sochi, plenty of snow, and Russia won the most medals. However, while the games were still ongoing Russian soldiers began streaming into the Crimean peninsula, just a few hundred miles to the west. Days after the closing ceremony, Russia formally annexed Crimea, and Kozak was appointed to manage Crimea’s integration into Russia. Within a few weeks, pro-Russian militants seized the southern portion of the Donbass, and the conflict threatened to spiral into full-scale war before the European Union offered to mediate.

These efforts led to the signing of the Minsk Protocols. These two agreements attempted to establish both a lasting ceasefire and a basis for future peace negotiations between pro-Russian secessionists and the Ukrainian government. Although Kozak had not been involved initially, he became the Kremlin’s informal point man on the Donbass in 2020. Simultaneously, he managed a complicated balancing act in Moldova, brokering talks between the pro-Western Party of Action and Solidarity and the pro-Russian Party of Socialists to marginalize Vladimir Plahotniuc, an anti-Russian populist. The unlikely coalition survived for two years, forcing Plahotniuc out of Moldovan politics altogether. This would prove to be Kozak’s last victory.

A Dove in the Hawk’s Talons

As Putin warmed to the idea of a full-scale war with Ukraine, Kozak was one of the few figures in the Kremlin counseling against it. Beginning in 2020, Kozak regularly met with Andriy Yermak, who then served as Ukrainian President Zelenskyy’s chief of staff. Kozak and Yermak brokered the basis of an agreement that could accomplish Putin’s substantive goals: Ukrainian state neutrality, official recognition for the Russian language, autonomy for the separatists in the Donbass, and Ukrainian acceptance of the annexation of Crimea.

By 2021, Zelenskyy’s unstable government had begun to lean on the pro-Russian Opposition Bloc for parliamentary support, increasing Russian leverage and making a peace agreement seem even more likely. But just as a peace resolution neared in late 2021, Putin was hellbent on war with Ukraine. Kozak initiated an intense effort to avoid war, attempting to convince the Ukrainian government to agree to neutrality and drafting a comprehensive agreement in January 2022. It was no use. Putin launched the invasion in February 2022, and the ever-loyal Kozak called Yermak, demanding a Ukrainian surrender.

Despite this failure, Kozak remained the most vocal supporter of a negotiated peace in Ukraine among Kremlin officials. He managed the Russian delegation at the Istanbul peace conference but was removed after failing to persuade the Ukrainian delegation to cede territory. Putin slowly iced Kozak out of foreign policy decision-making, replacing him with another ethnic Ukrainian, Sergei Kiriyenko, who is far more hawkish than Kozak. With little to do and alienated from his long-time patron, Kozak finally departed in September 2025.

🌎Why It Matters🌎

The exact reasons for Kozak’s dismissal remain unknown. He may really be planning to enter the private sector, a guilty conscience may have finally caught up with him, or he might just be the latest victim of Kremlin intrigue. His resignation, however, has occurred amid a dramatic escalation by Russia against NATO. Just a week before his resignation, 21 Russian drones violated Polish airspace. Four days before Kozak’s resignation, another Russian drone entered Romanian airspace, and two days after Kozak’s resignation, three Russian fighter jets breached Estonian airspace.

The departure of the Kremlin’s most prominent dove, coupled with these escalations, suggest that Putin has given up on a negotiated end to the war in Ukraine. Putin’s inner circle is now completely composed of hawks, with prominent officials like Dmitry Medvedev warning that “the risk of direct conflict [with the United States] remains high.” Meanwhile, Trump has urged NATO members in Eastern Europe to shoot down Russian planes and drones that enter NATO airspace.

For 25 years, Kozak, the Cheshire Cat, handled Putin’s toughest challenges, but since the invasion, he has faded away like his namesake. Without diplomatically-inclined officials like Kozak to temper the aggressive impulses of the Kremlin, a Russian provocation could spiral into war between NATO and Russia. The last dove in the Kremlin has flown away, and only the hawks remain, eyes fixed towards Europe.