The South Caucasus—home to Azerbaijan, Georgia, and Armenia—is a geographic region that oftentimes is believed not to have developed regionalism. The reason for such an argument is the lack of political stability caused by security and territorial issues. With the ceasefire truce brokered by Russia and the declaration of Azerbaijan’s victory in the Second Karabakh war, new regional perspectives are in sight for the region. As the winner of the war, Azerbaijan has the opportunity to reshape the regional dynamics of the South Caucasus. Nonetheless, theories on regional leadership suggest that a country must satisfy a set of conditions before it is able to aspire to this position in a regional context. Using data on capabilities and the literature on diplomatic behaviour, this paper suggests that Azerbaijan has the means to promote a regional order in the Caucasus, but such a project will largely depend on the policies that Azerbaijan will foster regionally in the short term and how they will be arranged with Armenia, Georgia, and the regional powers neighbouring the South Caucasus.