This paper investigates the role of artification‐based philanthropy in enhancing brand authenticity and addressing the luxury brand paradox through the case study of Ornellaia's Vendemmia d’artista project. The infusion of art undoubtedly enhances brand perception, particularly for luxury brands that seek to reinforce prestige and exclusivity. On the other hand, philanthropy is a powerful tool to improve brand image by demonstrating the brand's genuine commitment to the common good and strengthening its symbolic value. Thus, for luxury brands, artification‐based philanthropy can be challenging due to the contradiction between the goal of philanthropic activity and the essence of luxury and exclusivity reinforced by art. Through in‐depth qualitative interviews with managers and analysis of internal documents, we investigated the Vendemmia d’artista project as an excellent example of how different initiatives can overcome this contradiction. Particularly, these initiatives include engaging in meaningful dialogue with stakeholders and the public, firmly establishing a strong connection with the brand identity, and committing to long‐term engagement with artists and the Solomon R. Guggenheim Foundation. The article outlines the proper use of artification‐based philanthropy in sectors where brand authenticity is essential for gaining legitimacy among the public and stakeholders. Additionally, it suggests managers prioritize unwavering commitment, strengthened by aligning multiple activities engaging diverse audiences.