How do you know what a corporate person is really intending, whoever exactly that person is? This chapter explores a set of initial answers to this question in philosophies of intention like Elizabeth Anscombe’s, in historical political cartoons of the corporation, in legal theories of contracts, and in Frank Norris’s The Octopus, the influential novel about the railroad colossus known as the Southern Pacific. Together, they fill out the problem of collective social intention both as it was understood around the turn of the twentieth century and how it developed subsequently. Although older accounts of contract appeal to intention (“a meeting of minds”), the corporate form’s lack of inner life and composite quality made such a mind-meeting odd to envision. The difficulty of knowing a corporate person’s meaning raised knotty issues of interpretation, and political cartoons provided a popular attempt to work through these issues. Other thinkers, including law professor Ernst Freund and Justice Oliver Wendell Holmes, Jr., resolved these problems in their theories of corporate contracts, which introduced a larger concern of how to interpret any of a corporation’s signs. This issue occupied philosophers like Charles Sanders Peirce, and later scholars of contracts such as Arthur Corbin. Ultimately, an attempt to resolve a particular problem of corporate contracts led to a semiological theory committed to the simple literality of signs, in order to negotiate how to live with collective beings without obvious or singular minds.