One of the most remarkable operations carried out in the Royal Infirmary of Edinburgh during the early decades of the 19th century was the surgical excision of an enormous tumour, believed to be an osteosarcoma, of the lower jaw of Robert Penman, that produced severe disfigurement of his face. James Syme, then in his late twenties, was invited to see the patient by Professor Ballingall and Dr John Abercrombie and, in July 1828, he operated, without the benefit of an anaesthetic, to completely remove the tumour. The patient not only survived the operation, but also remained in excellent health for many years afterwards. He emigrated to the United States, but occasionally returned home to Scotland. In 1855, Lord Lister, who noted that his "deformity" had been wonderfully masked by a bushy beard, saw him. This case is re-evaluated in the light of information from the archives in the Royal College of Surgeons of Edinburgh and from the contemporary and more recent literature.