Yevgeny Prigozhin, founder of the Wagner private mercenary group, was tragically onboard a plane crash, marking the possible end of a journey that saw him transform from being referred to as Vladimir Putin’s “personal chef” to leading an insurrection that challenged Putin’s rule. Prigozhin’s path was paved through Russia’s tumultuous post-Soviet economy, but his prominence came with Wagner’s involvement in Russia’s Ukraine invasion. He led a rebellion against Putin’s handling of the war, a move that shocked many considering his close ties to the Kremlin. After halting his armed advance towards Moscow through a deal brokered by Belarus, Prigozhin evaded criminal charges, sparking speculation about his fate. This contrasts with the fates of other Putin critics, leading to questions about potential political motivations behind the plane crash. The article delves into Prigozhin’s background, his connections with Putin dating back to their modest origins in St. Petersburg, and his transformation from an oligarch into a warlord. Prigozhin’s Wagner group gained international attention for their mercenary actions in various conflict zones, and he extended his influence through activities like operating a Russian troll farm that interfered with the 2016 US presidential election. His rebellion against the Kremlin, his critique of Russia’s military leaders, and his vocal opposition to their strategies set the stage for his eventual downfall. The tragic plane crash serves as a poignant chapter in the complex story of Yevgeny Prigozhin’s rise and fall.