In 1980, the Danish and British trade union movement were arguably two of the most powerful in the world. But over the next three decades their fortunes diverged dramatically. This chapter adds a new element to this well-worn story by exploring the cases of two exemplary union-owned newspapers in Denmark and Britain: The Daily Herald (1912–1964), once the world’s largest working-class newspaper operated by the British Trade Union Confederation; and Aktuelt (1871–2001), once one of the world’s oldest social democratic newspapers operated by the Danish Trade Union Confederation. The history of each newspaper is recounted before considering their respective closures during the period of ascending neoliberalism. The analysis shows how Danish trade unions were able to preserve their ability to produce news by reinvesting into a new range of media outlets while their British counterparts largely lost this power and concludes by reflecting on the contemporary significance of this divergence.