6. David O’Leary
In the 1996/97 season, Leeds’ last League title-winning manager Howard Wilkinson was relieved of his duties. His replacement was former Arsenal boss George Graham, back after serving a one-year ban for accepting illegal payments from agents in dodgy transfer deals. Graham installed his former Arsenal centre-back and Republic of Ireland international David O’Leary –who had just finished his playing career at the Yorkshire Club- as his assistant manager.
Early in the 1998/99 season, Graham left after accepting the newly vacated managerial position at Tottenham Hotspurs. The board, therefore, decided to advance the young and untested assistant manager O’Leary.
O’Leary utilized the youthful exuberance of his squad in order to implement an energetic and attacking style of play in which emphasis was placed on being creative and pressing high up the pitch. This allowed technically gifted players such as Lee Bowyer and Harry Kewell, who had failed to flatter under Graham, to absolutely flourish.
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.
5. Dick Ray
Dick Ray was one of the most loyal servants ever at Elland Road, serving both Leeds City and United for well over thirty years, although he had a number of breaks from the place. As well as being the manager of United in two separate spells, he was also a player and captain of City, as well as being a committeeman and secretary with United.
In his first season in charge and Ray pushed Leeds back to division one. He stuck mainly with the good squad that was left by Fairclough and a significant signing by Ray was Charlie Keetley, who scored 18 goals in 16 appearances.
Ray quit his £1,000 a year post on 5 March 1935, deciding he had taken United as far as he could. A month later, he took over from Jack Peart as Bradford City manager.
4. Marcelo Bielsa
Marcelo Bielsa is one of the most influential football managers in the world. He became Leeds United’s new head coach in June 2018 to replace Paul Heckingbottom. He signed a two-year contract with the option of a third year, after two weeks of negotiations with the club. In doing so he became the highest-paid manager in Leeds United history.
Bielsa brought back Leeds United in the Premier League for the 2020-21 season. They were excellent in that season. Under him, Leeds played great football and attracted praise from all over the world. However, a poor following season led to his sacking in Feb 2022. No one could deny the contributions he made for the club.