Abstract The tension between the game of chess as strictly regulated by rules and the idea of freedom can be traced in three radidal examples separated by media and different periods of the twentieth century. The first emphatic employment of the concept of freedom is in the title of a chess journal issued by the Communist opposition of the central German working-class chess organization at the end of the Weimar Republic. In the journal Frei Schach! the radical subsection of “Red Sports Unity” asserts its claim for supremacy, demanding revolutionary goals in the class struggle. But this journalistic appeal to freedom was countered by the use of the same concept by the moderate alternative central chess organisation, and soon even by the National Socialists suppressing both working-class organisations. In the cultural scene after the second world war there was a distant, strangely depoliticized echo of freedom in chess. In the Austrian avantgarde dramatist Wolfgang Bauer`s version of Ibsen`s modernist revision of classical drama in the play Ghosts there is a farcical use of everyday objects as a replacement of chess elements. They function as a postmodern parody of the conventional structures of a conversation play. Compared to such highly idiosyncratic ludic transformation of chess games, today`s digitalized chess in which the computer is the final arbiter makes the game more accessible to the masses. The surface democratic appeal in which average players can turn into critics of the chess elite is accompanied by the complete subjection to digitalisation on a late capitalist agenda. However, this does not completely deprive the traditional game of chess of its promise of playful enjoyment for an increasing number of people on a global scale.