Although female candidates began to appear in leader elections of the largest Finnish political parties already by the late 1980s, women were not elected before the 21st century. This study examines women’s breakthrough to party leadership in Finland by analysing the reporting of leader successions in the main Finnish newspapers. The appearance of the first female candidates was greeted with bewilderment: women’s ‘eagerness’ to reach top positions was seen as aggressive and exaggerated. However, this attitude soon changed and female candidates began to be favoured by the media especially when the party in question had lost support and suffered a negative image. Gender stereotypes remained typical throughout the period: choosing a female leader was seen as a more positive ‘message’ but also as riskier choice than choosing a male.