He read medicine at the University of St Andrews, returning after service with the Royal Northumberland Fusiliers and the King's African Rifles during World War II to study history and economics.
[1][2] After leaving MI5, he worked in the City at stockbroking firm Standard Industrial Group, before joining merchant bank Lazard, where he became the first director to resign in over 100 years.
[3] Cuckney was appointed chairman of the Mersey Docks and Harbour Board in 1970, which he restructured and restored to viability following the possibility of insolvency.
[6] Cuckney had gained a reputation as a "the company doctor who never lost a patient" following his involvement with the Mersey Docks and Harbour Board, Crown Agents, and John Brown.
In 1992 he was appointed as an advisor to Peter Lilley, Secretary of State for Social Security, following the death of Robert Maxwell and the discovery that he had stolen hundreds of millions of pounds from his companies' pension funds.