Borut Pahor is one of the most successful Slovenian career politicians and one of the very few Slovenian statesmen. He was a member of parliament, speaker of the National Assembly, member of the European Parliament, and prime minister and president of the Republic. He is practically the only contemporary Slovenian politician to have held all three highest state leadership positions during his political career: head of parliament, head of government and president of the Republic. At the beginning of his political career, he had a clear vision and clear goals, which he has fully achieved. People love and hate him, mainly because he always knew how to choose unconventional methods to impress the public, be it a slip-up at a high school parade, an unusual friendship with the Croatian prime minister, an extravagant Instagram profile (he was named European Instagram President by Politico) or completely unconventional political campaigns. In this chapter, we will analyse his political career and show that Borut Pahor is undoubtedly a charismatic leader. We will also find out whether Borut Pahor is indeed a populist leader or whether his unique political style is simply too specific for today’s politics, and he is unapologetically misunderstood as a populist leader.