Business Masculinity represents a distinctly English configuration of masculinity that was hegemonic in the City of London’s banking and finance industry until recently. This work uses visual semiotic analysis, historical analysis and Bourdieusian concepts to show how Rothschild reproduced the aesthetics of Business Masculinity in the portrait A View from the Royal Exchange (1817) by using clothing and other symbolic cultural capital. To secure his trajectory, Rothschild needed to align his identity with Business Masculinity and thus Englishness – and disassociate himself from Jewish masculinity – in a culture of antisemitism, as well as deal with the repercussions arising from his alleged manipulation of information about the Battle of Waterloo (1815). In this context, the portrait played a significant part in Rothschild’s public identity-management. Shortly after the portrait’s publication, Rothschild was trusted with key information and opportunities which were conducive to his enterprise growing exponentially. It is suggested that the portrait played a hitherto underacknowledged part in Rothschild’s trajectory, by disassociating Rothschild from Jewish masculinity and associating Rothschild with Business Masculinity.