Turkish President Recep Tayyip Erdoğan is on the verge of crossing Russia's red line as the Nagorno-Karabakh conflict is different from Syria and Libya, Kerim Has, a Moscow-based Russian and Turkish affairs analyst told Ahval in a podcast.

On Oct. 1, Andrey Kortunov, director-general of the Russian International Affairs Council, a think-tank affiliated with the Russia's Foreign Ministry, said the relationship between Erdoğan and his Russian counterpart Vladimir Putin was a minefield, and the Turkish president might have crossed the line and was close to stepping on a mine with its involvement in Nagorno-Karabakh.

"Although the red line has not been crossed yet, Erdoğan is poking Putin's nerve endings," Has said.

The relationship between the two leaders was already strained before fighting broke out around Nagorno-Karabakh on Sep. 27, he said.

Russia and Turkey have managed to establish a relationship that is mutually beneficial but also fraught with complications in the Syrian and Libyan civil wars, where the two support opposing sides. They are strategic partners and competitors at the same time, even direct opponents in some cases. 

However, Nagorno-Karabakh has a distinct significance for Russia, the analyst said. The two countries have had either military advisers, mercenaries or troops deployed on in Syria and Libya, but similar Turkish efforts in Nagorno-Karabakh, a former Soviet stomping ground in close proximity to Russia, could lead to unintentional escalation and permanent destruction of the partnership, he added.

"Putin will not allow more Turkish interference in Karabakh, which is known as Russia's backyard," Has said. 

Russia enjoys good relations with both sides in the conflict: it has a defence pact with Armenia, its traditional ally, and recently fostered warmer ties with Azerbaijan. Moscow also sells arms to both countries.

Turkey, on its part, has not hid its support for Azerbaijan as they share long-standing cultural, historic and economic ties. Ankara provided military support to the Azeri government for the fighting that broke out with Armenian separatists on Sept. 27.

Armenia, Russia, France and Iran all accused Turkey of deploying Syrian fighters to Azerbaijan. The Russian Foreign Ministry said last week that it was “deeply concerned” by the deployment of Syrian and Libyan militiamen to the Nagorno-Karabakh region.

The Syrian Observatory for Human Rights, an opposition war monitor, reported around 900 Syrian mercenaries were transported to Azerbaijan by private Turkish security companies since the clashes started. Members of the Syrian National Army, a group of Turkey-backed opposition militias in northern Syria, told Foreign Policy that such transfers happened even before the fighting. Both Turkey and Azerbaijan deny such reports.

Turkey instrumentalised foreign mercenaries to exert influence on several fronts, Has said. "Putin comes within an inch of publicly announcing that jihadists were sent to Nagorno-Karabakh through Turkey."

Putin is reserving his true feelings of resentment over Turkey’s intervention as part of a strategy to punish Armenian Prime Minister Nikol Pashinyan and his government that resists returning into Russia’s sphere of influence, the analyst said.

One of Pashinyan’s pre-election promises when he came to power following a series of anti-government protests that unseated a Moscow-friendly administration was to reduce Armenia’s reliance on Russia.

The Russian president has been successfully using Armenia’s phobia of Turkey in his gambit to restore control over the country, Has said.

"The reckoning of the Pashinyan administration with Russian and pro-Russian names and flirting with the West caused Moscow to view the threat of Baku (the Azeri government) from a favourable perspective."

Has said Erdoğan's recent move to test its Russian-made S-400 missile systems should be seen as an effort to calm relations with Putin.

On Tuesday, Turkey began moving its Russian S-400 missile defence systems to a training ground near western province of Sinop for testing. 

"The unveiling of S-400s in Sinop is again based on political calculations. Although it is not activated at the moment, it will be activated sooner or later," he said.

Tensions between NATO allies Turkey and the United States over the S-400 air defence systems appeared to come to a head in April when Erdoğan and his government announced plans to activate them.

However, the costly activation has been delayed for the foreseeable future, with Turkish authorities citing technical issues and the coronavirus pandemic.

Washington has threatened Ankara with sanctions and suspended Turkey from the programme to build and operate the fifth generation F-35 fighter jet last year after Turkey bought the S-400s, which the United States maintains are not compatible with NATO defence systems and threaten the F-35’s stealth capabilities.

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