Hugh O'Leary

Hugh Richard O'Leary was born on 19 July 1974 in Allerton, Liverpool, England. He was raised in Heswall, located on the Wirral Peninsula, as the eldest of three siblings. His mother, Susan (née Dunn), worked as a nurse, and his father, John O'Leary, was a college lecturer who trained as a solicitor and worked for the legal firm of Liverpool lawyer Rex Makin.

O'Leary attended Birkenhead School, where he studied Mathematics and Further Mathematics at A-level. He applied to Oxford University to study Philosophy, Politics, and Economics (PPE) but was not successful. He subsequently enrolled at the London School of Economics (LSE), where he studied econometrics and mathematical economics.

Following his university education, O'Leary became an accountant. His career included work as a finance director at Affinity Global Real Estate and employment at Arrakis Investments Limited, a company characterized by having no employees aside from its sole director at that time.

In the realm of politics, Hugh O'Leary has been affiliated with the Conservative Party. He has run unsuccessfully for local council positions in the Greenwich London Borough Council elections on multiple occasions. In 1998, he was a candidate for the St Alfege ward, which was held by Labour. In 2002, he contested Greenwich West; in that election, Labour secured all three seats. His most recent attempt was in 2006, in the Charlton ward, where opposition candidates, including O'Leary, finished behind Labour contenders. During this period, his wife, Liz Truss, was elected to represent the Eltham South ward, serving until 2010. In 2022, O'Leary remained active in Conservative activities and canvassed with the party in Greenwich.

O'Leary and Liz Truss met at the 1997 Conservative Party Conference in Blackpool. Their first date involved ice-skating, an activity during which O'Leary sprained his ankle. The couple married in 2000. They reside in Greenwich, southeast London, and also in the South West Norfolk constituency, which Truss represented from 2010 until 2024.

His personal life includes two daughters. O'Leary maintained his relationship with Truss following her 2004–2005 extramarital affair with Conservative Member of Parliament Mark Field, which resulted in the breakdown of Field's marriage to Michele Acton.