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They have been, for several years now, the bad boys on the eastern fringes of Europe. Two leaders with little time for Western concepts of democracy, two strongmen with foreign policies coloured by dreams of empires lost.

Now – after a Russian warplane was shot down Tuesday after allegedly crossing into Turkish airspace while carrying out a bombing mission in Syria – Russian President Vladimir Putin and Turkish President Recep Tayyip Erdogan stand nose to nose, snarling, each counting on the other to blink first.

It's an incredibly dangerous standoff, one that seems certain to increasingly inflame Syria's civil war and to push any hope of peace further into the distance. As the most serious clash between a NATO ally and the Russian military since the Korean War, it also has the potential to drag the NATO alliance into greater confrontation with Russia. (At an emergency meeting called by Turkey following the downing of the Russian plane, NATO ambassadors asked Turkey to show "cool-headedness" and avoid escalation.)

Until Tuesday, Mr. Putin and Mr. Erdogan seemed to see kindred spirits in the other. They've met or spoken dozens of times over the decade-plus that each man has dominated their countries' politics, emphasizing every time the growing friendship between their two states. They know – and seemed to like – each other as well as any two leaders on the international stage.

Mr. Putin's initial response to Tuesday's incident was dripping with a sense of betrayal. "Today's loss is a stab in our back delivered by the accomplices of terrorists. I cannot find another wording for what happened today," he said during a meeting with King Abdullah II of Jordan.

"Our plane and our pilots were in no way a threat to the Turkish Republic in any way. This is obvious," Mr. Putin went on.

Photos and video published by Turkish media showed the Russian Su-24 warplane with flames coming from one of its engines hurtling toward a forested mountain – apparently Turkmen Mountain in Syria's northwestern Latakia province – while two white shapes that appeared to be parachutes floated through the clear blue sky.

Syrian rebels later posted video of a dead Russian pilot, badly bloodied, as well as a separate video that appeared to show the destruction of a Russian helicopter sent to rescue the two pilots. The fate of the pilots remained unclear.

In a 15-page submission to the United Nations Security Council, of which Russia is a permanent member, Turkey said two planes had approached Turkish airspace on Tuesday morning and were warned 10 times in five minutes to change direction. It said one of the planes left Turkish airspace and the other one was fired at by Turkish F-16s.

"Today's tragic event will have significant consequences for Russian-Turkish relations," Mr. Putin warned.

The extent of those consequences – and how Turkey might respond – is what's rattling nerves across the Western Hemisphere. The first blows will be economic: Russian Foreign Minister Sergei Lavrov cancelled his scheduled visit to Ankara on Wednesday and told Russian tourists, who account for 12 per cent of all visits to Turkey, that they should also avoid the country.

There were changes in military posture, too. Russia's defence ministry announced Tuesday that all military-to-military contacts with Turkey would be frozen. The missile cruiser Moskva was being redeployed to the Latakia coast in the wake of the incident, the Russian military said, and fighter planes would now escort Russian ground-attack aircraft on all missions over Syria.

But the real test of the relationship will be in the routes those Russian warplanes take from now on. Turkey – worried by the gains that the forces of Syrian President Bashar al-Assad have made since Russia started providing air support in September – has been calling for a no-fly zone in northern Syria for some time now.

On Friday, Mr. Erdogan's government called in the Russian ambassador to specifically complain about Russian air strikes targeting the ethnic Turkmen population in the Turkmen Mountain area, where Russia's Su-24 warplane crashed on Tuesday. Turkmen are Syrians of Turkish descent and their militia, the Syrian Turkmen Army, is backed by Ankara.

It's the two leaders themselves who make Tuesday's incident so combustible. Both have a long track record of escalating conflicts, and counting on their opponents to back down – or crushing them when they don't.

Over his 15 years in power as Russia's President or Prime Minister, Mr. Putin has smashed Chechnya's separatist movement, invaded tiny Georgia to make a point, seized the Crimean Peninsula from Ukraine to make another one, and crushed his domestic opposition. He has openly mourned the fall of the Soviet Union and made an ideology out of defending ethnic Russians wherever they live.

In his 12 years as Turkey's President or Prime Minister, Mr. Erdogan has bombed Iraq's Kurds, then his own Kurds, and now Syria's Kurds. He has used deadly force to crush protests, and curbed Turkey's once-vibrant media. He has played with fire throughout Syria's war, allowing rebel groups of all stripes (including jihadis who grew into the so-called Islamic State) to use Turkish territory as a rear base against the Assad regime.

As often as Mr. Putin is accused of nostalgia for the USSR's domination of its neighbours, Mr. Erdogan is accused of seeking to restore the Ottoman Empire's lost influence in parts of the Middle East.

Though the two leaders have disagreed, vehemently at times, over issues ranging from Chechnya to Syria to Ukraine, Mr. Putin and Mr. Erdogan had remained close partners, expanding their countries' economic relationship even as the West ratcheted up sanctions against Russia over Ukraine.

When the European Union pressured member state Bulgaria to cancel a planned Russian gas pipeline across its territory, Turkey stepped into the void and offered to act as a transit state for Russian energy. When Mr. Putin travelled to Ankara on a state visit last year, he was met at the airport by Mr. Erdogan and their motorcade was escorted by a liveried horse guard through the city to Mr. Erdogan's newly built presidential palace. A modern sultan receiving today's tsar.

Ironically, it is their similarities that have brought their countries close to conflict: Mr. Putin's attachment to an old Soviet ally, the Assad dynasty, is at odds with Mr. Erdogan's dreams of restored Turkish hegemony over the region.

The loss of a fighter jet is not likely to affect Mr. Putin's determination to preserve at least the remnants of Mr. al-Assad's regime. "We will never tolerate such crimes like the one committed today," Mr. Putin snarled Tuesday.

Nor, having delivered a rough message to his erstwhile friend, is Mr. Erdogan likely to back down now from his drive to remake Turkey's neighbourhood.

World leaders including U.S. President Barack Obama and French President François Hollande on Tuesday were urging Moscow and Ankara to avoid escalation, to let cooler heads prevail.

But there's little in the track records of either Mr. Putin or Mr. Erdogan to suggest that it would be wise to bet on caution prevailing.

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