David O'Leary

O'Leary was born in Stoke Newington, London, on 2 May 1958, and moved to live in Dublin in 1961.

Arsenal

O'Leary had two weeks on trial at Manchester United before signing for Arsenal as an apprentice in 1973. He made his debut against Burnley on 16 August 1975 in a 3–3 draw, and despite being only 17, went on to make 30 appearances that season. The following year, he signed a professional contract. For the next 10 years, he played more than 40 matches a season (except for 1980–81, when he was out with an ankle injury and only played 27). A calm and collected central defender, O'Leary was noted for his good positioning and elegant style of play. He won his first major honour with Arsenal when he played in their 3–2 win over Manchester United in the 1979 FA Cup final. He also played in the 1978 and 1980 Cup finals, and the 1980 European Cup Winners' Cup final, all of which Arsenal lost. The same year, he was nominated for the Ballon d'Or. In 1982, O'Leary became club captain but relinquished it to Graham Rix 18 months later. In 1981, O'Leary rejected a move to Manchester United and signed a four-year extension at Arsenal. He missed the loss to Luton Town in the 1988 Football League Cup final due to an Achilles tendon rupture. O'Leary broke numerous appearance records at Arsenal; he was the youngest person to reach the 100- and 200-match milestones, and he made his 400th appearance while still only 26. He passed George Armstrong's all-time record of 621 first-team…

O'Leary's international debut with the Republic of Ireland came as a teenager in a 1–1 friendly draw with England on 8 September 1976. Following the appointment of Jack Charlton, O'Leary was frozen out of the international setup for two years. After being left out of a squad for a mini tournament in Iceland in May 1986, O'Leary booked a family holiday, which he decided not to cancel when he was eventually asked up to the squad following several withdrawals. O'Leary did not feature until November 1988, thus missing out on Euro 88. The highlight of his 68-cap international career came in the 1990 World Cup. With Ireland in a penalty shootout with Romania, Packie Bonner saved Daniel Timofte's last penalty. O'Leary then stepped up to take the decisive final penalty to win the shootout 5–4 to take Ireland to the quarterfinals. O'Leary's strike has since been voted as the greatest moment in Irish footballing history. On 17 October 1990, O'Leary scored his only goal for the Republic of Ireland in a 5–0 win over Turkey in a Euro 92 qualifier. O'Leary was captain in his final international game on 17 February 1993, but was injured in the opening minutes of the 2–1 friendly win over Wales at Tolka Park.

Leeds United

When the former Arsenal manager George Graham was put in charge at Leeds United in September 1996, O'Leary was installed as his assistant. He remained in this position for two years. On 29 September 1998, in Graham's last match as manager, O'Leary was sent off for arguing with match officials in a UEFA Cup first-round game away to C.S. Marítimo, which Leeds won on penalties. Graham left for Tottenham Hotspur, and on O'Leary's debut as caretaker on 3 October, Leeds lost 1–0 at home to Leicester City, managed by Martin O'Neill who was linked with the Leeds job. After a goalless draw with Chelsea at Elland Road on 25 October, chairman Peter Ridsdale gave the job permanently to O'Leary on a 21⁄2-year deal for a salary of £600,000, then one of the highest salaries for managers in England. At the end of the 1998–99 season, Leeds finished fourth in the Premier League and qualified for the UEFA Cup. Their 1999-2000 UEFA Cup campaign ended in the semifinal with defeat to the Turkish side Galatasaray, following the murders of two Leeds fans during violence the night before. On the domestic front, Leeds finished third in the Premier League and qualified for the Champions League. It was their first campaign at this level since the 1992–93 season. In August 2000, O'Leary signed a six-year contract, for which he would earn £10 million. Leeds reached the semifinals of the Champions League in 2000-01, where they lost to eventual runners-up Valencia. Their Premier League…

O'Leary's father was an avid Arsenal supporter who had left Ireland to work in London as a contractor, and was later proud that his son chose Arsenal instead of Manchester United, who had also offered him terms to sign for them. O'Leary is a UK resident according to current UK Companies House documents, and maintains links to Yorkshire. He has been married to wife Joy for more than forty years. In 2002 she was the subject of hate mail during a failed CPS prosecution of two Leeds football players. The couple have two children together. O'Leary's brother, Pierce, played for Shamrock Rovers and Celtic, and was capped seven times for the Republic of Ireland. His nephew, Ryan, declined to play for the Republic of Ireland Under-21s, choosing to play for Scotland, the country of his birth. O'Leary endorsed a Game Boy Color game called O'Leary Manager 2000, which was released by Ubi Soft in 2000. O'Leary was involved in a complex tax avoidance scheme, O'Leary v. McKinlay (Inspector of Taxes), that was struck down in the Chancery Court in December 1990. The scheme involved the loan of £266,000 (equivalent to £657,790 in 2025) by Arsenal, O'Leary's club, to trustees in Jersey, where it was held for his benefit.