Putin the Planner


Observers commonly describe Vladimir Putin’s invasion of Ukraine as a reckless gamble. But the Putin I came to know in St. Petersburg during the early 1990s was not a gambler in the classic sense, much less a reckless one. Gambling by definition involves the risk of losing. My interactions with and observations of Putin showed that he did not like taking such risks. Rather, he carefully planned his moves, combining intimidation, violence, and legal maneuvers in a systematic way to achieve his ends. Putin only acted once he thought that the outcome was almost certain to be a success and he persisted, using additional resources as necessary, until he achieved his goal.

Analysts have cited a variety of miscalculations in Putin’s recent decision-making, but this does not mean that he was rolling the dice. Putin viewed Ukraine as an unresolved problem. He took steps over a period of years that he thought would ensure the success of an invasion. Once he could no longer wait for an alternative solution, Putin launched it at the most opportune time. Whatever happens on the ground now, there is good reason to think that Putin will continue to pursue a solution on his terms as long as he remains in power.



Putin in St. Petersburg

During my tour of duty in the early 1990s at the U.S. Consulate General in St. Petersburg, I was able to hold regular, wide-ranging personal conversations with Putin over a period of almost 18 months. I met Putin soon after my arrival in 1992, when he was the official in charge of the city’s external relations and was designated by the mayor to be my interlocutor on a security issue. Shortly afterwards, Putin became a deputy mayor and my counterpart on every aspect of the city’s relations with the American community. We attended ceremonies and other events together, sometimes riding for hours around the countryside, which enabled me to probe his worldview and opinions on all aspects of politics and economics. The relationship initially was very cordial. But things turned sour after I began investigating organized crime in the city and briefing Western officials, journalists, and businessmen on activities that involved Putin.

During our conversations, Putin told me on numerous occasions that Russia needed to regain its status as a superpower. Putin did not trust the West: Western leaders were only helping Russia because it was in their own interest. Although Russia needed Western help to modernize, at some point Russia would need to go its own way and stand up for its interests. Part of Russia’s interests concerned the countries of the so-called “near abroad” (formerly part of the Soviet Union) that, Putin said, constituted Russia’s natural sphere of influence. He stated that those countries should be hewing a path carved out for them by Russia. In his conversations with me, Putin did not say that these countries should be reabsorbed by Russia, but he said multiple times that they were bound to Russia by tradition, and it was “natural” that they should act in concert with Russia.

Beyond the exposition of his worldview, a portrait emerged from my discussions with Putin, as well as from my conversations about him, that showed that he was a person who consistently sought to minimize risk. The overwhelming consensus in the city was that Putin did not undertake something if he felt that there was a chance he could lose: He acted only if he was supremely confident of winning and only after making meticulous preparations. When Putin judged the odds to be most in his favor, he acted decisively. And once he had started something, he was determined to see it through, using all means at his disposal. Putin only stood down or sought an accommodation when instructed to by a higher authority or if confronted with countervailing force.

As head of the city administration’s external relations department, Putin was in charge of licensing companies and regulating foreign investment in the city as well as export activities through the city’s port. After he became deputy mayor, Putin added oversight of law enforcement, including the tax and organized crime police units, and of the city’s administrative, hotel, justice, and public relations directorates to his portfolio. These additional responsibilities provided Putin with the resources he needed to dominate the city.  He utilized the combination of licensing and regulating, together with law enforcement, to develop a blueprint for seizing control of companies and even whole sectors of the city’s economy.

Putin’s Modus Operandi

Putin’s first foray into asset seizures was not a success, as he admitted in his autobiography. In 1991, the mayor issued a directive giving Putin supervision of the gambling industry. Putin obtained an in-house legal ruling that the city could claim 51 percent ownership of the casinos’ gambling activities if it relinquished the right to collect rent on the casinos’ premises. Putin then formed a joint stock company to collect the proceeds. The problem, however, was that there were no proceeds. The organized crime families that ran the casinos cooked their books so they reported only losses. In summing up the experience, Putin stated “ours was a classic mistake made by people encountering the free market for the first time … We hadn’t thought things through sufficiently.” He concluded by saying that if he had not left for Moscow, he would have “squeezed” the casinos “to the end” to force them to share their profits with the city.

Putin’s determination that he would not fail again because of insufficient planning showed in his subsequent successful efforts to seize ownership of real estate and businesses. Sometimes the model operated in a relatively straightforward way. In 1992, for example, Putin wanted land on a lake near the Finnish border to build dachas for himself and his coterie. First he utilized an existing trust fund to make the purchase of two small plots for himself. Then he used intimidation and bribery to drive out the owners of neighboring plots. Once their land was vacated, members of Putin’s inner circle obtained ownership.  They all then formed the Ozero Dacha Cooperative to funnel in money for the construction of their estates, but also to use for other purposes.

At other times, such as during the effort to take control of the St. Petersburg port, operations became much more complex. Putin began by seizing the commercial Baltic Sea Fleet, one of the port’s prime assets. He had the police arrest the incumbent director on charges of embezzlement, enabling him to pick the successor. The fleet was then sold off at reduced prices to newly created dummy corporations that in turn sold the ships for their real value. To quell resistance to the scheme, one long-time member of the fleet’s board who objected was murdered. However the port’s other key asset, its oil terminal, presented a more difficult task. It had become a bone of contention between rival mafia gangs who were not prepared to give up their stakes without a fight. To sidestep such a fight, Putin’s external relations committee formed a joint venture with a company run by ex-KGB associates to build new oil terminals away from the existing port. Threats from the gangs and the death of a key negotiator, possibly poisoned by the mafia, scuttled the idea. Instead, Putin and his associates formed an alliance with a mafia leader who had obtained de facto control over the oil terminal, with Putin legitimizing the control by issuing government licenses.  Putin then issued licenses that would let his own associates legally use the oil terminal for their import and export activities.

Putin’s reputation for ruthlessness and vindictiveness went beyond simply using force to overcome opposition to his schemes. He would pursue opponents and critics for a long time, waiting to get even. While still in St. Petersburg, Putin had the organized crime police beat up and imprison a former city aide who went public about financial corruption in the city government. After Putin became prime minister in 1999, he pursued the former city official, who was imprisoned again — this time for life. The former city official died in prison in 2014. Putin similarly pursued a St. Petersburg city legislator who in 1992 investigated Putin and unsuccessfully urged his removal from office for concluding bogus contracts. After the legislator published an article in 2000 opposing Putin’s candidacy for president, she was subject to intimidation that persuaded her to leave politics and go into hiding. She only came out of hiding shortly before her death in 2012.

Unfinished Business with Ukraine

Putin followed his St. Petersburg model on a national scale once he became president. Whether operating against oligarchs or political opponents such as regional governors, Putin first dismantled their existing structures of control — either through application of force or by law. Then he created new vehicles for control, putting members of his circle in charge of them. Then through application of law, Putin legitimized his new vehicles of control, while using force to uphold his new legal arrangements.

The model was less successful internationally where opponents had greater resources to resist. Putin tried to justify his interference in Georgian affairs legally, but his use of force in 2008 only succeeded in wresting away control over a portion of Georgian territory.  Since at least the 2004 Ukrainian presidential election campaign, Putin tried to intervene in Ukrainian politics to prevent Kyiv from zigzagging between pro-Russian and pro-Western administrations. But in both the 2004 Orange Revolution and 2014 Maidan Revolution, Ukrainians rejected his attempts to do so.

When Russian-backed president Viktor Yanukovych failed to regain his seat after being ousted by the 2014 revolution, he called the event a coup. Putin echoed this charge, but he did not attempt to restore Yanukovych to the Ukrainian presidency. Instead, in March 2014 he moved to seize and then annex the Crimea, and in April sent Russian troops into the Donbas to support the proclamation of separatist governments in Donetsk and Luhansk. Fighting between the Ukrainian army and the separatists continued through 2014 until a stalemate was codified in the February 2015 Minsk agreement. In Russia’s interpretation, this meant that the separatist regions would hold a veto over Ukraine’s foreign policy.

One of the puzzles of the 2014 crisis is why there was no Russian attempt to topple the new pro-Western Ukrainian government. Putin told European Commission President Jose Manuel Barroso in September of that year that he could “take Kiev in two weeks” if he wanted to. But whether he meant it or not, he never tried. Were Western sanctions hitting Russia harder than Putin let on? Was he underwhelmed by his military’s performance in support of the separatists? Was he persuaded that the band-aid provided by the Minsk agreement would provide time for a more compliant Ukrainian government to take power?

If the exact reason why Putin did not go further in 2014 remains opaque, the seeds of Putin’s decision to invade this February were already planted. In his annual question-and-answer broadcast that year, Putin criticized the Ukrainian government’s conduct towards the separatists and reminded them that Russian parliament had authorized him to use force in Ukraine. This publicly-expressed dissatisfaction suggests that Putin may have begun planning then for the necessity of taking more forceful action in the future.

The Necessity to Act

The final decision to launch the invasion on Feb. 24, 2022, seems to be the result of a confluence of factors. Putin felt the need to resolve unfinished business from 2014, while developments in late 2021 made him believe that the problem was coming to a head and the time was right for resolving it.

The more Ukraine turned westward, the greater it became a problem for Putin. A Ukraine integrated into any Western structure, whether NATO or the European Union, would deal a major blow to Putin’s efforts to restore Russia’s greatness. Putin believed that he had to prevent this from happening. Ukrainian President Petro Poroshenko’s escalation of the military effort against the separatists reduced the territory under their control. Poroshenko’s continued search for an association agreement with the European Union was also worrisome. His defeat by Volodymyr Zelensky in the 2019 presidential election, however, seemed to offer a ray of hope, as Zelensky’s campaign platform called for a settlement to end the conflict with the separatists.

The possibility of improved relations disappeared, however, when Zelensky changed his approach to dealing with the separatists and took a number of steps that antagonized Putin. First, in December 2019, negotiations between Putin and Zelensky went nowhere when Zelensky said he wanted to amend the Minsk agreement. Zelensky then made a renewed push for an association agreement with the European Union and membership in NATO. He also aroused Putin’s ire by shutting down several pro-Russian television stations and pressing treason charges against a close friend of Putin’s for funding the separatists.

Complicating matters was the strained personal relationship between Putin and Zelensky. Before Zelensky became Ukraine’s president, he had starred in a hit television series that poked fun at Putin, something Putin has not tolerated since his St. Petersburg days. Upon Zelensky’s election, Putin offered Russian passports to the Donbas population, to which Zelensky gave a mocking response. This set the tone for further such exchanges, which probably made Zelensky into a personal target of Putin’s invasion.

Still, there was no reason for Putin to act so long as Donald Trump was president. Putin saw Trump weakening NATO by bashing it verbally, questioning whether the United States should honor Article 5, and reportedly flirting with the idea of withdrawing completely. If NATO might self-destruct, then there was no need for Putin to act to prevent Ukraine from joining it.

Putin had to change his calculus after Trump’s defeat in 2020. Joe Biden took steps to reassure allies of the U.S. commitment to NATO. Although there was nothing in NATO’s official statements to suggest that Ukraine could or would obtain membership at a definite point in time, the change in the U.S. attitude towards the alliance, combined with Zelensky’s support for membership, meant that the Ukraine problem became more acute. The timing might appear to be coincidental, but just a few months after Biden took office, the Russian military build-up began on Ukraine’s borders. This development fits with Putin’s penchant for planning carefully before taking action. It also suggests that Putin may already have made the decision to invade.

Improving the Odds of Success

A key element of Putin’s plan to return Russia to the superpower status of the Soviet Union involved restoring Russia’s military might. He increased military spending, instituted military reforms, and developed new weaponry. The payoff was somewhat evident in Russia’s prosecution of its war with Georgia in 2008, but more so in its incursions into Crimea and the Donbas in 2014, and most striking in the Russian intervention in Syria in 2015.

Putin also bolstered Russia’s nuclear capability, its primary claim to military superiority. He announced the acquisition of additional intercontinental ballistic missiles in 2015, deployed more nuclear attack submarines in 2016, and tested new ground-launched cruise missiles in 2017. In a 2018 speech, Putin warned the West that Russia had developed new “invincible” nuclear weapons. He re-emphasized Russia’s longstanding first-use doctrine in the Feb. 27 statement in which he announced he had ordered Russia’s nuclear forces into “special combat readiness.”

Putin also took steps to bolster Russia’s economic strength and independence from the West. Following Western sanctions on Russia over the annexation of Crimea, Putin reportedly began to build a treasure chest of foreign currency and gold, which reached $630 billion by 2022. His economic advisers developed independent Russian financial infrastructure, reduced Russia’s dollar holdings, and switched energy transactions to euros or yuan. Russia also reduced imports from the West and turned to trade with China as a substitute. Putin sought to increase Europe’s existing dependence on Russia’s oil and natural gas, which in 2014 had made the Europeans reluctant to impose sanctions. At the same time, Putin tried to reduce Russia’s reciprocal economic dependence on Europe by making long-term energy deals with China.

Seizing the Moment

In this connection, the completion of Nord Stream 2 pipeline in September 2021 offered Putin leverage with Germany and an opportunity to split Western unity. Both governments wanted the pipeline despite the opposition it aroused from a number of EU governments and the United States. Although the pipeline opening was delayed by a certification issue, Putin could hope that its promise, so close to realization, would make the Germans think carefully before joining any effort to sanction Russia.

Other developments suggested the last part of 2021 would be an opportune time for Putin to act. The chaotic U.S. withdrawal from Afghanistan in August raised questions about American military commitments abroad and resulted in considerable domestic criticism of the Biden administration. In addition, Biden’s continued trouble in passing his domestic agenda could only contribute to a perception that the administration was weak and would not be able to oppose Putin effectively.

The final factor suggesting to Putin that the moment was propitious for him to act was the retirement of Angela Merkel and the replacement of her Christian Democrat-led coalition by a Social Democrat-led one. Merkel and Putin had had a complicated relationship. Merkel had sought to maintain a working relationship, which included support for the Nord Stream 2 pipeline as an economic link between the two countries. While this has generated criticism, Merkel also had a history of rebuking Putin on human rights. As part of her vocal opposition to Putin’s behavior in Crimea and Donbas, she had insisted that the sanctions imposed on Russia in 2014 should only be lifted if Moscow made progress on implementing the Minsk accord. The problem for Putin was that Merkel had become the most respected leader of the NATO alliance following Trump’s election and she was in a position to organize effective opposition to further steps against Ukraine.

Just as important as Merkel’s departure was the fact that the new German Chancellor, Olaf Scholz, was something of a blank slate. He had been Merkel’s vice-chancellor for several years, but his foreign policy views were largely unknown. The Social Democrats had long been a party that sought normalization and cooperation with first the Soviet Union and then Russia. This meant that Putin could hope that the new German government, especially mindful of the promise of Nord Stream 2, would be more accommodating than Merkel had been. He may have even hoped that Germany, and perhaps some other European states dependent on Russian energy, would respond to military pressure on Ukraine by offering some concessions to Putin’s diplomatic demands.

If the turnover in the German government recommended December as a launching time, the Beijing Olympics constituted an obvious reason to delay. Reliable press reports suggest that Chinese leader Xi Jinping made a request to Putin to delay the invasion until after Beijing’s showcase Olympic Games had concluded. Putin’s desire to continue consolidating relations with Beijing would have given him good reason to grant this request. He stalled throughout January by engaging in diplomatic talks with the United States that the State Department on Feb. 25 said had been a “charade.” Assuming that these reports are correct (and it is hard to see Russia’s maximalist demand to roll back NATO to its 1997 configuration as a serious starting point for negotiations), this means that the actual launch decision was probably made in mid-December.

Putin Won’t Give Up

If Putin began thinking about an eventual invasion of Ukraine after the crisis of 2014, his thinking most likely only crystalized following his failed talks with Zelensky in 2019. While Trump was president, Putin could still hope to resolve the problem some other way. But Biden’s election foreshadowed a revitalization of NATO, so Putin needed to act. He believed that he had insulated Russia from Western sanctions and, as demonstrated in Crimea and Syria, successfully rebuilt the Russian army.

Against this backdrop, preparations for military action began in earnest in the spring of 2021. With their completion in the fall of 2021, the only question remaining was exactly when to launch. The completion of Nord Stream 2 and the retirement of Merkel recommended December, but the favor to Xi delayed the invasion until February. For the invasion to start so immediately after the close of the Olympic Games, everything had to be in place and ready to go before then.

There’s a particularly ominous aspect of Putin’s character that was clear to those of us who knew him. Since his St. Petersburg days, his response to opposition has been to stay the course until he overcomes all resistance. If Putin’s meticulous planning fails, and he perhaps has to settle for seizing just the Donbas region, it will mean another failure on his part to solve the Ukraine problem. Given his single-minded desire for a fully compliant Ukraine and his determination to finish what he starts, no one should expect such an outcome to be the end of the story. Putin’s vindictive character and his longstanding modus operandi suggest that he would view this as a temporary setback, much like in 2014. This means that at some time in the future he would again seek to bring Ukraine to heel.



Andrew Goodman retired from the Senior Foreign Service in 2009 after over 30 years mostly devoted to dealing with the USSR and Russia. He has taught courses on Russian foreign policy at Columbia University, the University of Massachusetts Amherst, and Mary Washington University.

Image: CC BY 4.0, The Kremlin