In Canary Wharf, London, inside HSBC’s head office and within the private meeting rooms on the 35th floor, the George Rae room can be found. Inside, lies a portrait of George Rae. George Rae’s connection to the HSBC was as the manager of one of its constituent banks, the North and South Wales Bank, in the second half of the nineteenth century. These images tell a story of a corporation’s past success and of its winners. This paper examines the visual representations of personnel connected to these banking institutions. Who was a winner? What does success look like? Do these images capture a broad and diverse range of races, ethnicities, genders and social backgrounds? Do these portraits tell a self-perpetuating story for who should succeed in banking? This paper uses portraits, oral testimonies and staff records, alongside bank archives to examine the ways in which these images and the stories behind them were commissioned, told and, in some cases, forgotten.