The skyline of London is composed of historic monuments of national and international importance, punctuated tall buildings built during post-war building booms, particularly since the 1960s. Currently, some of the tallest commercial and residential buildings are under construction and the emerging skyline is intended to reflect London’s premier world city status, as a stable global capital that balances finance and culture within an integrated society. Its skyline image has been managed since 2000 by the Mayor of London through the London Plan. This paper will consider the historical, intellectual and policy basis that has permitted – indeed encouraged – the introduction of tall buildings into central London since 2000 by focussing on the design of the Heron Tower, located at the northern edge of the Eastern Cluster of tall buildings in the City of London, and discussions regarding its visual impact on St Paul’s Cathedral. Drawings explore the visual impact of the City’s tall buildings on a famous view of St Paul’s from Waterloo Bridge, and highlight the subjectivity of visual inter-relationships experienced locally in the context of the persuasiveness of global finance.