Two decades ago the US sought to play a role in Russia’s backyard, the former Soviet Republics in the Caucasus. It was part of an overall effort by western powers, including the European Union and NATO, to export their influence into places like the Baltic states and Ukraine. In the Caucasus the western powers set their hopes on Georgia and Azerbaijan and Armenia, but Russia’s influence was quietly rebuilt over the years. On October 8 Moscow moved to stop fighting between Azerbaijan and Armenia by inviting the countries to Moscow for talks. Vladimir Putin, Russia’s ruler for the last decades, has a worldview that was formulated during the era of Soviet decline. He joined the KGB in the 1970s. It was the Kosovo crisis in the late 1990s that led Putin to understand how far Russia’s ability to influence international affairs had fallen. In power, Putin has worked to slowly and methodically rebuild Russia’s military and diplomatic power. He crushed Chechan “separatists” in campaigns from 2000 to 2002 and humiliated Georgia in a 2008 war. In 2014 Russia annexed Crimea from Ukraine and helped set up two breakaway republics in eastern Ukraine. These operations have illustrated that there are red lines beyond with countries cannot go when dealing with Russia today. Russia has lost out in the Baltics, where the three states joined NATO in 2004. Moscow was also concerned about western arms sales to the Czech Republic and Poland over the years. It has sought to shore that up with closer work with Serbia and other countries in eastern and Central Europe, as well as using gas and energy as a way to push influence. Across the Black Sea, Russia has partnered with Turkey on the Turk Stream pipeline and has sold S-400s to Turkey to pull it away from NATO. Russia also signed deals with Ankara over disputes in Syria and has worked with Turkey closely at talks in Astana and Sochi where the countries have agreed that they both want the US to leave Syria. However, in the Caucasus represent a challenge for Moscow. Azerbaijan has been seeking closer work with NATO since 1992. In 2002, it became an associate member and joined the NATO Operational Capabilities Concept in March 2004. It is very clear how Moscow has reacted. In 2020 the Kavkaz military drills in the region included some 80,000 personnel and soldiers from Armenia, Belarus, China, Iran, Myanmar and Pakistan. Not Azerbaijan or Georgia. Nevertheless, Russia wants to continue its historic role in the southern Caucasus. Towards that end when fighting broke out on September 27 Moscow called for a ceasefire. Turkey has backed Azerbaijan with weapons sales such as drones and even sent its own F-16s and mercenaries from Syria. This raises eyebrows in Moscow. Putin thus invited foreign ministers to talks on October 9. Russia supports Azerbaijan’s claims to Nagorno-Karabakh but wants a peaceful resolution. Iran has said the same thing. Unlike Turkey’s government, which thrives on war and crises, Moscow wants these conflicts to be frozen and more quiet. That is Moscow’s way, the way it works in Ukraine or Libya, Syria and elsewhere. Minimum footprint, maximum influence. Armenian Prime Minister Nikol Pashinyan has been speaking frequently with Moscow. However, he is not Moscow’s favorite. Russia has indicated it stands by Armenia in self-defense, but not Nagorno-Karabakh, an area run by Armenians but claimed by Azerbaijan since fighting in the 1990s. Fighting has flared in 2014 and 2016. Russia’s goal is to show it can mediate the conflict, as it has done in Syria and make Moscow the go between for numerous countries. This appeals to Moscow’s desire to become a world diplomatic power again. While European countries express concern and put out statements, they have not successfully helped solve a conflict in decades. For instance Geneva talks, backed by Europe, the UN and former US Secretary of State John Kerry, failed to stop fighting in Syria. It was Iran, Turkey and Russia, working via Astana meetings since 2017, that stopped the fighting. Moscow likes this because it helped solidify the Syrian regime gains. Turkey likes this because it got to take northern Syria and expel Kurds. Iran likes this because it gets to use Syria as a highway for weapons to supply Hezbollah. Turkey, Russia and Iran toast with tea over having isolated the US in eastern Syria and eroding US partners among the Syrian Democratic Forces. The end goal for Moscow is to make them leave the Middle East and other areas the way Russia was humiliated in 1999 in the Balkans. It has taken twenty year to get revenge for NATO swooping into Kosovo in 1999. Today Russia is the one hosting the talks and seeking to give its stamp of approval. In Moscow’s view the days of NATO or the EU doing anything except putting out statements is largely over. Russia will hold court and others will come to Russia to get things done. The question now is whether Moscow can succeed in the southern Caucasus, or whether Ankara’s meddling and other agendas will undermine Putin’s decisions. Russia knows Turkey is practicing with the S-400 system this month and Russia is hosting the Egyptian navy in the Black Sea. These are tense and complex times. Russia’s chess game could come undone if Putin is not careful.