It's a tough question, with various layers, and might make Putin himself pause. Here's an attempt at an answer.
Putin wants to win; he wants victory. So how he would he define victory? First, he must be able to rule securely till 2024, as a constitutional amendment he enacted allows. Securing that outcome means ensuring that key supporters are able to preserve something resembling their present privileges of power, wealth and status.
That in turn requires that the Russian people continue passively to accept his rule and whatever role in politics he gives them. At present that amounts to endorsing him every six years at an orchestrated election. The legitimising ideology of strident anti-Western nationalism that he and his advisors have formulated (Russia is a victim of serial injustices and besieged by enemies that covet its riches and seek to dismember it) might be effective enough to secure that quiescence. But Putin's decision to set up a National Guard and his gradual tightening of restrictions on freedoms of assembly and speech suggest he isn't counting on it. That's why for him it is vital to maintain spending on pensions, student stipends and the like.
Putin is a career secret-service officer and a martial-arts practitioner, and was a street fighter as a kid in Leningrad, or so his biographers say. Success in all three requires victory. He has quoted Stalin's maxim that 'the weak get beaten', and respects strength, guile, skill and daring. He doesn't believe in 'win-win' outcomes, unless no other desirable outcome is feasible (as in, say, managing relations with China).
Although he eventually got into the elite Soviet organisation that he worshipped – the KGB – he failed to reach its senior ranks. His sole posting was to East Germany, not a genuinely foreign assignment. Perhaps that in part explains why Putin exhibits a chronic need for affirmation: the personality cult, the self-glorification, the resentments and so on.
Someone who knows him said recently that Putin is 'a Brezhnev-era KGB officer still seeking retribution for the Soviet Union's defeat in Afghanistan'. [fold]
Putin didn't serve in Afghanistan, but for a KGB officer the defeat there may well symbolise 'defeat' in the Cold War. And for him the decisive factor in the humiliation was US support for Russia's foe, the Afghan Mujahideen. It's widely accepted in Russia that the failed campaign was crucial in the Soviet Union's downfall, famously described by Putin as a 'tragedy' and a 'geopolitical catastrophe'. But the revised, Kremlin-endorsed version of the collapse, now standard in history textbooks, is that it was the realisation of a long-term strategy conceived by President Carter's National Security Adviser Zbigniew Brzezinski and executed by the CIA.
For Putin the US remains, in KGB-ese, the 'Chief Adversary'. The venom with which the Kremlin-controlled Russian media depicts the US and Obama is difficult to convey. Secretary of Russia's National Security Council, Nikolai Patrushev, asserts that American enmity towards Russia is 'systemic, immanent and permanent'.
So winning means, above all, victory over the US. That means erasing the outcomes of the Cold War and regathering what Putin would see as Russia's lost lands, either by direct incorporation or by re-asserting de facto control. According to AV Filippov's Contemporary Russian History, 1945-1991 – A Guide for Teachers, 'Moscow is of the view that Russia's present borders are unnatural in the sense that they do not guarantee a reasonable level of national security.'
Putin wants borders that provide such a guarantee – and obviously it is for Russia to define what 'a reasonable level' means. He has thrice used military force, unilaterally, without credible provocation, and each time without recourse to international mediation, to realign Russia's borders.
In the short term, Putin wants an end to the sanctions imposed after the seizure of Crimea and shooting down of MH17 in east Ukraine. The Kremlin insists the sanctions are counterproductive but they are hurting, especially in regards to technology that Russia lacks to tap its Arctic oil and gas fields. Putin needs lots of money and accepts that he mustn't just print it. Energy exports are by far the most lucrative source. Putin supports Trump, assessing that a Trump victory will, among other desirable things (the worse for the US, the better), mean an end to sanctions. Sanctions are one reason that Brexit has given him intense satisfaction. Having identified an opening to use calculated bluster to widen the cracks in the creaking enemy alliance, he has just renewed his own counter-sanctions for a further 18 months.
Second, he wants MH17 to be forgotten. He may think that to deny Russian complicity was, in hindsight, a mistake: the shooting down was clearly an error. To acknowledge that the Donetsk-Lugansk separatists were to blame might have pre-empted sanctions.
Third, he wants acceptance of Russia's revised borders, that is, de facto recognition of the incorporation into Russia of the nominally independent former Georgian territories of Abkhazia and South Ossetia – and Crimea.
Fourth, he wants to force Ukraine to accept Russian tutelage, in the form of an amendment to the Ukrainian constitution giving a veto over foreign policy decisions to the Donetsk and Lushansk 'autonomous regions', or some equivalent outcome. Over the longer term he wants a secure, pro-Moscow government in Kyiv.
In this context Putin would presumably be glad to see the back of Angela Merkel, who has become a key obstacle to dismantling the sanctions, and whom he has alienated irrevocably by lying to her repeatedly.
Ultimately, Putin likely wants a 'special relationship' with a compliant Germany. A senior diplomat, Aleksandr Kramarenko, has argued that Germany is 'Europe's natural leader' and should therefore replace the UK as a permanent member of the UN Security Council. Post-Brexit that proposal may be pursued with more commitment.
In the medium term, over the next five or so years, Putin wants to see the collapse of the EU and NATO – that is, the US out of Europe, where he believes it has no right to be. He told NATO's former Secretary General Fogh Rasmussen publicly that he wanted the alliance abolished.
His dismissal of the EU as 'a wretched little hamster' (khomiachok) was eloquent. Even more so is his bankrolling of anti-EU, far-right parties in France, Hungary and, it stands to reason, other countries. They are his natural allies, genuinely admire him and would, presumably, like to emulate him. The response to Brexit of Boris Titov, a member of the Putinist elite, was telling: Brexit 'will separate Europe from the Anglo-Saxons…this is not the independence of Britain from Europe but of Europe from the US.'
In the Indo-Pacific, Putin would doubtless sympathise with the efforts of his like-minded friend Xi Jinping to force the US out of East Asia. Russia advocates a 'new system of indivisible security for the Asia Pacific'. This presupposes the dissolution of existing regional military alliances such as ANZUS.
Finally, Putin wants to see the emergence of an entity he grandiloquently calls the 'Eurasian Union'. This is in essence Putin's ultimate answer to 'The West', a reconstituted Russian empire in a 21st century form, with the central Asian states becoming, in effect, Russian protectorates, but constructed so as not to upset the Chinese. This entity would be the dominant partner in what Putin has called a 'Greater Europe', from 'Lisbon to Vladivostok'. The other partner would a German-led 'Romano-German' EU. Both entities would cooperate closely while preserving their respective 'civilisations' (in Putin's version of Russian history, Russia is a separate civilisation, not a mere culture). From Putin's viewpoint this wish list (or definition of victory) presumably looks legitimate and achievable.
Putin believes Russia was defeated in the Cold War by guile, conspiracy and traitors – that is, Gorbachev and his supporters. Putin's Minister for Culture, Vladimir Medinsky, has described Gorbachev's perestroika as a 'disaster for the Russian people', and Russian schoolchildren are now taught that Gorbachev's role in Russian history was malign.
But post Brexit, with disarray in Europe reinforcing 'Ukraine fatigue' and given the prospect of a Trump presidency come November, Putin may have concluded that, with help from 'our Western partners', as he sardonically puts it, Russia is winning the Cold Peace.
Photo (both): Getty Images/Sasha Mordovets