The Russian annexation of Crimea 2014 was a successful special operation that shed light on the Russian ability to conduct covert operations with a high degree of deniability to achieve its political and strategic goals. Sholars suggested that this kind of operation was part of the new Russian hybrid warfare. Later, not few scholars found the term hybrid warfare problematic in cases of describing all Russian actions against Ukraine, which diluted the concept. It is clear that some segments of Russian actions in Crimea definitely can be categorized as hybrid warfare but doing so one may risk oversimplifying Russian foreign policy and to lose important aspects of understanding the Russian intents. While scholars have pointed out that the concept of hybrid warfare is not comprehensive to understand the annexation of Crime, this study aims to contribute with the perspective of the conditions of a successful special operation. This study applies Gray's (1999) theory to analyze the success of the Russian special forces operation during the annexation of Crimea. The findings reveal that the high training level of Russian special forces allowed for a smaller, more efficient force capable of swift and covert operations. This resulted in tactical surprise and the rapid exploitation of Ukrainian vulnerabilities, leading to a strategic advantage. Key factors included prior intelligence gathering and the timing of the operation, which coincided with a period of weakness in the Ukrainian military. The analysis concludes that the tactical success of the special forces was crucial for the overall strategic outcome of the operation.