The present chapter explores the appointment, work, and legacy of the noted British constitutionalist Sir Ivor Jennings (1903-1965) as constitutional advisor to the Nepal Government in the late 1950s. Jennings visited Kathmandu for one month from 28 March to 24 April 1958. He was employed by the British Foreign Office (FO) upon the request of the Nepali monarch, King Mahendra Bikram Shah, to advise the small Commission charged with the drafting of the Constitution of the Kingdom of Nepal 1959 – the third constitutional document in the country’s history. In 1941, Jennings had moved to Sri Lanka, where he resided until 1955. While in Sri Lanka, he became progressively involved with constitution-making processes and constitutional politics in the decolonising world. This period of Jennings’ life, the body of literature pertaining to the postcolonial world that he produced, and his advisory work in decolonising countries is referred to here as the ‘Oriental Jennings’.1 It is argued here that his work in/on South Asia represents the core of the academic production and advisory work of the ‘Oriental Jennings’.2 Aside from Britain – Sri Lanka, India, and Pakistan were the countries Jennings was most familiar with and to whom he dedicated the majority of his academic writings.3 This essay maintains that Jennings’ constitutional advisory work in Nepal is crucial to understanding the progression of his thinking on constitutional democracy in both Asia and Britain