A wide variety of scholars acknowledge heritage planning as a widespread phenomenon. However, to what extent it is widespread is debatable. Also, if heritage planning is an acknowledged widespread phenomenon, what can be learned about it when looking at the rhetoric and the key concepts used in different contexts? This study aims at a cross-contextual investigation. The main aim is to interpret and to discuss rhetoric and underlying ideas used in heritage planning debates across contextual boundaries. The main aim is made workable through a number of methodological choices that curtail the scope of the study. The following main question is the result of these choices; what kinds of arguments, metaphors and figures of thought are similar (context-independent) versus different (context-dependent) in a selection of recent and on-going debates about heritage planning from Malmö and Rotterdam? As part of the methodology, figures of thought – that are expected to be relevant for understanding debates about heritage planning – are treated. This includes figures of thought such as the idea of an “original” and the idea of “progress”. Cases from the cities of Malmö and Rotterdam are chosen to study what similarities and differences come to the fore in heritage planning debates running parallel in time but being situated in different contexts (respectively a Swedish and a Dutch). The debates chosen are about the Kockums Crane and the area of Varvsstaden in Malmö and about the Porters Lodge and the area of RDM in Rotterdam. The analysis shows that the arguments and premises raised, the metaphors used and the underlying figures of thought are to a great extent similar between the cases from Malmö and the cases from Rotterdam. However, the use of arguments, metaphors and figures of thought differs professional groups in-between (“monument curators” versus “planners”) and between debates about single objects (the Kockums Crane and the Porters Lodge) and debates about the development of areas (Varvsstaden and the area of RDM). This study shows that arguments, metaphors and figures of thought effectively are exchanged across national boundaries through professions. More notable however, is that different “language-games” played or kinds of arguments used by monument curators and planners do not seem to conflict with each other at a discursive level. For example, the monument curator’s story-telling metaphors are smoothly turned into the planner’s commodification metaphors. However, at the level of figures of thought a potential conflict may arise between the preservationist idea of the moral duty of stewardship and the idea of commodification of built heritage propagated by an alliance between bureaucracy and economy.