By supporting Ukrainian separatists, they say, he took a huge risk but it largely paid off as it allowed him to punish Kiev's pro-Western authorities for seeking to turn their back on Russia and stand up to the West.
Most importantly for the Kremlin, the annexation of Crimea and support for fellow Russian speakers in Ukraine's east have given a huge boost to Putin's popularity ratings at home.
According to a February study from the Levada Centre independent polling group, the number of people who want Putin to seek a fourth term in 2018 has more than doubled to 57 percent since December 2013.
"What Putin wanted was clear a year ago -- he wanted a blocking stake in Ukraine or -- the next best option -- a manageable conflict," Nikolai Petrov, a professor at the Higher School of Economics, told AFP.
"To a large degree the Kremlin has achieved what it wanted."
Ukraine marks the first anniversary of the start of the conflict in a hugely demoralised state with its economy shattered and NATO membership a very distant, if not impossible, prospect.
"They managed to keep Ukraine out of NATO because it is struggling with two unresolved territorial disputes," Alexander Baunov, a senior associate at the Carnegie Moscow Center, told AFP.
If Putin gambled that the West would not move to burn all its bridges with Russia nor engage the former Cold War foe militarily, he was right.
While Washington has been vocal in its assertion that Moscow has been sending troops over the border to buttress Ukrainian separatists, it has held off on supplying Kiev with lethal weapons over fears of escalation.
Economy-wise, the US and European Union have forged a united front, slapping Russia with several rounds of sanctions, but decided against radical measures like cutting Moscow off from the SWIFT banking system.
Russia has withstood the blow, and the government recently declared that the worst was over for the recession-hit economy.
After a shock slump late last year, the Russian ruble has recently rebounded following a lull in fighting in Ukraine and the steadying of oil prices.
Economists have forecast stagnation over the next few years but naysayers predicting imminent financial collapse have been floored.
In a sign that Putin may be getting ready to break out of Western isolation, he is considering whether to travel to New York to speak at the 70th session of the UN General Assembly this fall, the Kremlin said.
It would be his first UN visit over the past 10 years.
Such a move would have appeared unimaginable several months ago when Putin appeared crushed under the weight of international condemnation when a Malaysia Airlines Boeing came down over rebel-held Ukraine, killing all 298 people on board.
The West and Kiev claim that Moscow-backed rebels shot the jet out of the skies by mistake, with a missile provided by Russia.
In a bid to counter raging accusations that he was personally guilty, an ashen-faced Putin recorded an unprecedented nighttime video address, urging the West and Kiev not to exploit the tragedy for political gains.
But as a shaky truce appears to be taking hold in Ukraine, Russia has apparently managed to put the worst of the fallout behind it.
That may explain Putin's jokey mood at the triumphant celebrations marking one year since the takeover of Crimea last month when he quipped that Russia "will overcome the difficulties that we have so easily created for ourselves."
'Putin will not back off'
To a large extent, Putin has been lucky, after rushing into the confrontation with the West without a well-thought-out plan, observers said.
"There was a set of tasks and Napoleon's famous maxim, 'On s'engage et puis on voit' (Let's jump into the fray and then figure out what to do next)," Konstantin Kalachev, head of the Political Expert Group think tank, said of the president's attitude.
Even if his tactics have often defied comprehension, Putin has made his message abundantly clear: the West should understand that a new, post-Soviet Russia is a force to be reckoned with.
"Putin will neither give up nor back off," Dmitry Trenin, director of the Carnegie Moscow Center, wrote in a recent report.
"Moscow will continue to defy US global hegemony and act in its own self-interest, guided by its own set of values and without seeking prior US or EU approval."
The fighting has exacted a huge human toll. According to official statistics, more than 6,000 people have died in eastern Ukraine since last April, and human rights activists say scores of Russian troops sent over the border have also perished in the ex-Soviet country.
Ties between ordinary Russians and Ukrainians have also been torn apart, with observers saying years -- if not decades -- will be needed to heal the rift.
While the fighting has largely died down, an end to the Ukrainian crisis is nowhere in sight.
"The crisis is dragging on through inertia, which is dangerous," said Petrov of the Higher School of Economics.
"It has become a necessity to a large number of people."