Turkey’s assertive foreign policy towards the former sphere of influence has changed the balance of power in the region. Erdogan, reclaiming the country’s past glory and reviving his kind of Ottoman Empire, stated that their republic is a continuation of the Ottoman Empire. To achieve his goal, he has become the master of Brinkmanship by his region’s policies lately. The advances in the Caucasus by Turkey to expand its influences, the conflict is facing complications. In this ongoing territorial dispute between Armenia-Azerbaijan, Turkey declared its full support to Azerbaijan, giving her upper hand in the recent quarrels and gradually isolating Armenia. Turkey has vehement relations with Azerbaijan culturally, ethnically, politically and economically. Cooperation in the field of energy is very crucial to mention. Azerbaijan exports 6 billion cubic meters gas to Turkey, making Turkey a bridge to supply Azeri gas onwards to Europe. Bilateral trade has reached more than $2 Billion, and both countries have agreed to maximize it further to $15 billion by 2030. Foreign direct investment of Azerbaijan in Turkey has reached $17 Billion, making it one of the largest foreign investors. If the state oil company of Azerbaijan completes all of its ongoing projects, it will reach up to $19 billion. Azerbaijan has many of its oil refineries in Turkey. Ankara was the leader of trade with Azerbaijan among OIC countries in 2020. Azerbaijan ranks second in the total volume of Turkish gas imports from the Caspian Sea. The area of conflict, Nagorno-Karabakh concerns because it is a significant oil and gas pipeline corridor. Moreover, the gas pipeline hosted by Azerbaijan is the alternate route to fuel supplies not only to Turkey but also to Europe. This geo-economic aspect has increased the importance, a little more, of the Caucasian conflict. The resolution of the battle is viewed as unlikely without the accord of  Moscow and Ankara. Turkish support to Azerbaijan in the decade long combat has now become a pretext for four possible references for Turkish interest in the conflict. First is the geo-economic factor of the partnership between the countries. Turkey sees Azerbaijan as a potential energy supplier country powering its industrial sector and sustaining its economic growth. To some extent, it would soon replace Russian oil and gas dependency with a country that is too easy for Turkey to control, unlike Russia. It is a challenge to regional hegemon Russia, preventing her from restraining Turkey’s actions in the long run on the Lutwakian model of geo-economic terms. Secondly, Azerbaijan has a corrupt government of Ilham Aliyev, which is under Erdogan’s control. Alleged by Armenia, Erdogan has possibly sent 4000 Syrian rebels militias to fight the Nagorno-Karabakh combat. Turkey would create an informal military base there to support and secure the friendly regime and, secondly, expand its influences into the Central Asian region. Azeri soil would become a probable political launchpad for Erdogan ambitions to reach Central Asia. The third is to test the military technology on the Azeri soil and make it an arms importer. Turkey has the long aim to lessen its foreign arms dependency from potential sellers, NATO members. Despite an arms embargo on Ankara by NATO countries, it had first bought S-400 from Russia to manage cordiality, which angered the US. Turkey clearly stated that it could address its military needs no matter if there is an embargo. Turkey is producing 70% of its military equipment and exporting them to regional states, making its 14^th largest arms exporter. Possibly Ankara would be testing its arms on the Azeri territory against Armenia, not to mention the sales to the conflicting party. Recent reports indicate that Baku has used drones against Armenia, which was made by a company named Bayrak Technical Company run by Berat Albayrak, Erdogan’s son in law which shows Turkey reaping benefits from the conflict which has an economic aspect. The fourth probable reason to flame the conflict and provoke Armenian forces is to pressurize and subdue Armenia in front of Turkish supported Azerbaijan so that Turkey can exert its indirect power on Armenia compel her to lay down knees against Ankara. Since the Armenian-Turkish border closure strategy was not proved beneficial for Turkey for a decade or so. The Nagorno-Karabakh dispute has interdependent geopolitical and geo-economic interests parallel to the strategic implications for NATO, Russia, to name a few other than Baku, Yerevan and Ankara. Turkey’s ambitious policies have the potential to alter the regional balance and to benefit from Balkanization. It has been saddled at odds against Russia, Arab and NATO countries over the Libyan and Syrian crisis. Ankara can’t afford the Caucasian conflict’s escalation over its territories amid the Russian-Armenian defense treaty 2010. However, neither Armenia nor Russia would be motivated against Turkish policies to take any military action to strain Turkey as it would invoke NATO’s Article 5. Moreover, Turkey is also at odds with its fellow member Greece in the Eastern Mediterranean, Agean Sea, on the energy exploration program outside its territorial waters, which Greece claims to be its exclusive economic zone. NATO countries are suggesting them to solve the dispute, avoid confrontation not by gun-boat strategy on both sides but in good faith to ensure the security of neighboring countries, preserve peace and international commercial interests in the East Med. Ambitious Erdogan has made big gambles in the region. Being a NATO member, it has given Ankara leverage to maneuver. However, these risky gambling with the inclusion of geo-economic strategy to support the Libyan GNA by using the coastal area Sirte have cohered the Arab nations like KSA, UAE and Egypt, allying with Greece to counter Turkish advance on power in the region. It seems to be encircled into the ring of enemies that want to contain Ankara. The Napoleonic policies (Napoleon III) to revive the lost French empire’s glory had proven to be disastrous to France, as history shows. It led countries to make the counter alliances to preserve Europe’s status quo, eventually isolating France. Emerging powers have reaped the benefits from the short-sighted behaviors and decision of territorial gains, relative advantages and influences that weakened France more. Paradoxically, Turkey is behaving like 19^th century France, desperate to be the core actor in international politics focusing on relative advantages. Initially, Erdogan should create his legacy not on the political design of those who were gradually becoming obsolete even before their collapse in 1922 but by setting examples of his own decisions. Merit, transparency, competency and the system of checks and balances in the contemporary period of intense communication, rapid flow information, and media are crucial for acquiring international support and domestic. Unfortunately, Morgenthau’s principle, animus dominandi is so inherent in human nature that no one can escape from it; however, the management could be done. Statesmen have a considerable responsibility and the most significant task to make crucial decisions. They should follow the long-term trends, reform their societies, take where it was never before as per contemporary world demands, complete risk assessments of his decisions, and take on competent board advisors to formulate the policies with broader knowledge. Erdogan should review his foreign policy decisions and avoid reckless stunts. However, plausibly the suppression of freedom of speech and trialing the political opponents is not a good move domestically for Erdogan. These policies would pave the way for his flux. If anyone of his calculation is disturbed by any external factor, the results will have huge costs for Turkish people and stability for the country. Soon, certainly by the policies, it seems like Eastern Question is rising again, and Turkey is getting sick once again as it was historically named, The Sick Man of Europe.