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. [3]
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. [8] 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. [13] 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. [14]
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. [15]
Leeds reached the semifinals of the Champions League in 2000-01, where they lost to eventual runners-up Valencia. Their Premier League form also dipped slightly and O'Leary's men had to settle for a UEFA Cup place, finishing fourth in the last season before the Champions League qualification spots for the English Premiership expanded from the top three to the top four. Although there was little indication of this at the time, this was a serious failure for the club because Ridsdale had borrowed £60 million against future gate receipts, budgeting for prolonged Champions League involvement.
The 2001–02 season began well for Leeds. They frequently topped the table during the first half of the season and were Premier League leaders on 1 January 2002, but a loss of form in the second half of the season had them slump into fifth place, again just outside the Champions League qualification spots, meaning that they would again have to settle for a UEFA Cup place.
Leeds players Jonathan Woodgate and Lee Bowyer were charged in an incident in Leeds city centre in January 2000, in which a man was beaten in what he believed was a racially motivated attack. In December 2001, Woodgate was convicted of affray and received 100 hours of community service, while Bowyer was acquitted. [16] In January 2002, O'Leary wrote a book, Leeds United on Trial. In it, he revealed that the club hired private investigators in the Bowyer and Woodgate affair, and said that he felt the police wanted to "put one over the club"; he also criticised The Football Association for freezing the pair out of England squads until the end of the trial. He also alleged that Jimmy Floyd Hasselbaink refused to play unless he could be the highest-paid player at the club. [17]
By June 2002, O'Leary had spent almost £100 million on new players in less than four years for no reward in terms of trophies, but he had never finished outside the top five as a manager. Ridsdale sacked O'Leary as Leeds manager in the summer of 2002, replacing him with Terry Venables. O'Leary's departure signalled a downhill spiral for the club – highly attributable to the financial state that saw the sale of several key players, which saw three more managers (Venables, Peter Reid, and Eddie Gray) come and go before the club was finally relegated from the Premier League in 2004 with £80 million debt, and fell into League One (the third tier of the league) three years later. This fall from grace led to the phrase "doing a Leeds". [18]
O'Leary's fame at Leeds rests upon his promotion of a series of younger players such as Woodgate, Bowyer, Alan Smith, Harry Kewell, Stephen McPhail, Eirik Bakke, Ian Harte, and Danny Mills (signed for £4 million from Charlton Athletic). He promoted several members of the youth team into an exciting Leeds side that played a pressing game relying on youthful enthusiasm. [19] In an interview regarding the decline of Leeds, O'Leary stated, "I never wanted to leave Leeds. The fans are fantastic to me here. I hope they stay up because I had great times at the club." [20]
O'Leary was fired with two years remaining of his contract and sued for compensation as the club claimed he had left by mutual consent. He settled with the club for £2 million and legal costs in February 2003. [21]
Aston Villa
After settling his case with Leeds, O'Leary was linked with Sunderland who had sacked Howard Wilkinson in March 2003. [22] On 21 May, he signed a three-year deal at Aston Villa, who had finished 16th under Graham Taylor. O'Leary targeted 6th place within two years. [23] His first game on 16 August was a 2–1 loss at newly promoted Portsmouth; The Guardian journalist Russell Thomas wrote "Punters who have already wagered on Portsmouth going down might now consider covering themselves by entering Aston Villa into the equation". [24]
In January 2004, O'Leary criticised chairman Doug Ellis for a lack of funding for transfers, as Villa had let go of 13 players while only signing Sunderland duo Thomas Sørensen and Gavin McCann for a combined £4.5 million; forward Dion Dublin had been playing in central defence. [25] The team finished in sixth place – one place too low for European qualification due to Millwall's FA Cup final appearance and Middlesbrough's League Cup triumph.
O'Leary signed AC Milan's international defender Martin Laursen, Carlton Cole from Chelsea, and French midfielder Mathieu Berson ahead of the 2004–05 season, in which Villa finished 10th in the league. [26] Despite six summer acquisitions including strikers Milan Baroš and Kevin Phillips, Villa finished 16th in 2005–06, just two places above the relegation zone. Following the relegation of local rivals Birmingham City and Bromwich Albion, Villa were the only Midlands side playing Premier League football in 2006–07. [27]
On 19 July 2006, O'Leary's contract as Aston Villa manager was terminated by mutual consent, after an investigation into a statement against Ellis allegedly given by the squad. [26] Ellis sold the club within a few days to Randy Lerner, and Martin O'Neill was appointed as manager. [28]
