Oluwale was born in Lagos, Nigeria, in 1930. In August 1949, he hid on board SS "Temple Bar", a cargo ship destined for Hull, England. When the ship docked in Hull on 3 September 1949, he was handed over to the authorities. Under the British Nationality Act 1948 Oluwale was considered a British subject and not an illegal immigrant, but he was charged as a stowaway under the Merchant Shipping Act. He was sentenced to 28 days' imprisonment, served in Armley Gaol, Leeds, and Northallerton Prison, Northallerton. Following his release from prison on 3 October 1949, Oluwale—who had served an apprenticeship as a tailor in Nigeria—headed to Leeds where there was a large textile and clothing industry. In 1953, Oluwale was charged with disorderly conduct and assault following a police raid on a nightclub. He subsequently served a 28-day sentence. In prison it was reported he suffered from hallucinations, possibly because of damage sustained from a truncheon blow during the arrest. He was transferred to Menston Asylum in Leeds (later called High Royds Hospital, now closed) where he spent the next eight years. He was treated with a variety of techniques, allegedly including electroconvulsive therapy and various drugs (hospital records have since been lost). Upon release Oluwale was unable to hold down a job and a permanent residence, and quickly became homeless. Friends reported that he was a shadow of his former self, and had lost all confidence. As a black man in a still overtly-racist Britain, his choices of lodging and employment were also limited in his lifetime (the Race Relations Act outlawing discrimination in both only received Royal Assent in October 1968). During this time he regularly moved between London, Sheffield and Leeds. He found himself in trouble with the Leeds police again several times and accused the police of harassing him. In late 1965, he was returned to High Royds Hospital, where he spent another two years. Following release he was once again homeless and lived on the street. Contemporary police records show that 1968 saw his first recorded contact with Sergeant Kenneth Kitching and Inspector Geoffrey Ellerker in Leeds. The actions of the two officers would allegedly lead to Oluwale's death, although several other police officers were also involved with harassing Oluwale during this time. In the subsequent enquiry and manslaughter/assault trial against Kitching and Ellerker, it was stated they regularly beat up Oluwale, often kicking him in the groin and, on one occasion, urinating on him.