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O'Connor was educated at Saint Columba's College, Dublin where he was a chorister and cricketer. From here he won a choral scholarship to Worcester College, Oxford but was unable to take it up due to the First World War.
Service in India
In 1915, he joined the Indian Army as an officer in the 14th (KGO) Ferozepore Sikhs. He was awarded the Military Cross "for distinguished and meritorious services" at the Battle of Sharqat, during the campaign in Mesopotamia against the Turks. Sir Kenneth later wrote a short account of the Battle of Sharqat. After the war he left the Indian Army with the rank of Captain, though he was later made an Honorary Colonel.
O'Connor then joined the Foreign & Political Department of the Government of India, serving as the British District Commissioner in Charsadda, a district of Northern India (now Pakistan) adjoining the Khyber Pass.
After a short time practising at the London Bar, he became a partner in the firm of Drew & Napier in Singapore. In Singapore, he met and married Margaret Helen Wise, the eldest daughter of the rubber planter Percy Furlong Wise, of the Devonshire dynasty.
Evacuation from Japanese occupation
As Chairman of the Straits Settlements Association, O'Connor played a key role in planning the civilian evacuation of the island in the event of a Japanese invasion. He escaped from Singapore in a small, open sailing boat with unsuitable sails and a children's atlas for navigation. Despite these impediments, with three others, he successfully sailed to Sumatra. O'Connor later wrote a short account of this adventure, entitled Four Men in a Boat. He had already evacuated his young family (Anthony, born 1933 and Hugh, born 1940) to Australia, where he later joined them.
Attorney General to the Colonial Legal Service
In 1943, having joined the Colonial Legal Service, O'Connor was appointed Attorney General of Nyasaland (now Malawi). After the war he returned to Singapore to reconstruct the legal practice of Drew & Napier. In 1946, he was appointed Attorney General of Malaya and in 1948, Attorney General of Kenya.
Africa and the Caribbean
Kenyan Mau Mau uprising
At this time, the Mau Mau Uprising was at its peak. O'Connor was the senior presiding judge in many Mau Mau trials, the most notable being that of Dedan Kimathi, whom O'Connor sentenced to death in 1957.
With Independence, Sir Kenneth and Lady O'Connor retired to their house, Buckland Court, in Surrey, England in 1962.
Sir Kenneth died on 13 January 1985, aged 88.
- Kabukuru, Wanjohi (March 2007). "From 'terrorist' to national hero". New African.