Years before Twitter, Fox News, or reality TV, Donald Trump became a public figure through his presence across a range of tabloid media. Although much of that focused on sex and spectacle, early tabloid coverage of Trump was surprisingly political, with speculation about a possible presidential campaign beginning as early as 1987. Through the theoretical lens of the political imaginary, this talk tracks the early articulation of Trump as political brand, the boundary-crossing media logics that shaped his public persona, and the political work the tabloids performed in building the foundations upon which the actual Trump presidency now stands.