Leeds United 1998-2002: David O’Leary and The ‘What If’ Generation

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by Dan Parry

It was 2001, Bob the Builder was fixing it, Robbie Williams was rocking DJ’s, Harry Potter and Lord of the Rings were ruling the cinemas, and in the football world Leeds United were on the verge of creating history. Manager David O’Leary and his ‘Babies’ (as he famously referred to them) were upsetting the domestic status quo of the time by challenging the dominant powers Manchester United and Arsenal, and due to a remarkable Champions League run it looked as though the side would go on to become a major force to reckoned with in Europe as well. The overwhelming belief was that the young squad would become a strong and constant presence in both the domestic league and in Europe. This conviction was so entrenched that Peter Ridsdale (Club Chairman) and the club’s board took out a £60 million loan leveraged against their confidence that title challenges and European qualification would become a norm.

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. These years at the club, both as a player and an assistant would be massively influential when it came to his time running the club. He became acquainted with the club’s famed Thorp Arch academy and its starlets. The crop of 1997 showed substantial potential when they won the FA youth cup and the side included future first team players such as Jonathan Woodgate, Paul Robinson, Stephen McPhail and Harry Kewell. Overall, Graham’s time at the club was solid albeit unspectacular; he brought stability, defensive solidity and the return of European football to Elland Road.

Early in the 1998/99 season Graham left after accepting the newly vacated managerial position at Tottenham Hotspurs. The board’s first choice replacement had been Martin O’Neill but he rejected their proposal and chose to stay with Midlands side Leicester City instead. The board therefore decided to advance the young and untested assistant manager O’Leary. In a shift from the Graham years O’Leary began to focus on the prodigious talents being produced by the academy, he blooded players from the 97 Youth Cup winning bunch into the main squad where their development continued alongside more experienced professionals such as: South African centre-back and Captain Lucas Radebe and the recently returned, Leeds-born, central midfielder David Batty.

O’Leary utilised 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. O’Leary’s philosophy was perhaps best epitomised by the young, homegrown forward Alan Smith. Promoted from the youth team by O’Leary, his determined and enthusiastic performances captured the hearts of the Leeds United fans. At the end of O’Leary’s first season Leeds finished in 4th place and qualified for the UEFA Cup for a second consecutive season.

Several changes were made for O’Leary’s second season in charge; Dutch striker and top scorer Jimmy Floyd Hasslebank went to Atletico Madrid for £12m, and older heads like David Wetherall and Lee Sharpe made way for fresh additions. Ridsdale opened the cheque-book and O’Leary spent £30m on promising British talents like Danny Mills (£4m, Charlton), Michael Bridges (£5m, Sunderland), Darren Huckerby (£4m, Coventry City), and Oliver Dacourt was imported from France (£7.2m, RC Lens). The investments paid dividends and the young side impressed as Leeds United produced one of their best seasons in recent memory. A remarkable run in the UEFA Cup lead them to the semi-final where they were knocked out on away goals by eventual winners Galatasaray. Even greater success came domestically as the fledgling side ended up in 3rd place and qualified for the Champions League for the first time in a decade.

With a European campaign in sight Ridsdale provided O’Leary with another blank cheque for the 2000/01 season. Aussie strongman Mark Viduka came from Celtic (£6.5m), Dominic Matteo crossed the Pennines from Liverpool (£5m), and a massive statement was made as Leeds broke the British transfer record to sign promising centre-back Rio Ferdinand (£18m). In Ferdinand, O’Leary saw a leader who he could build a Europe conquering team around, and the Irishman set about creating a footballing dynasty.

In 2000/2001 the exertions of competing in the Champions League midweek proved to be too much for the players’ young legs and caused their league form to falter. They ended up finishing in 4th just outside of the Champions League spots. The stand out performances came during that season’s Champions League as the young players repeatedly bested expectations on a dreamlike journey to the semi-finals.

In the first group stage they were drawn with Barcelona, AC Milan and Beskitas. Nobody gave them much chance of surviving the group, especially after an opening fixture in which they were drubbed 4-0 at the Nou Camp by Barcelona. But they produced some magnificent home performances, including a 6-0 hammering of Beskitas, and a 1-0 defeat of AC Milan that came thanks to some good fortune in the form of poor handling by Milan keeper Dida who fumbled a long range Bowyer effort into his own goal. Leeds came 2nd in the group, below AC Milan but above Barcelona, and went through to the second group phase stage. The second group phase draw was equally as difficult as the first, and yet again not many expected Leeds to qualify. Nevertheless, the young Leeds side showed their potential and churned-out some important victories to help them progress to the quarter finals. Famous away wins over Italian champions Lazio 1-0 and a 4-1 thrashing of Belgium’s Anderlecht left indelible marks in Leeds United’s history.

In the quarter finals they faced the reigning Spanish champions, Deportivo La Coruña. Certain players from Deportivo had stated that they were happy to have drawn Leeds United, describing them as the weakest side left in the tournament. The Leeds players used this criticism as motivation and it resulted in one of Leeds’ most memorable European nights. The inexperienced yet brave underdogs were completely unfazed by the situation and ran out unlikely 3-0 victors thanks to goals from Ian Harte, Leeds native Alan Smith and Rio Ferdinand. A 2-0 defeat in the away leg at El Riazor Stadium in La Coruña meant that Leeds United had done enough and they progressed to the semi-final where they faced the previous season’s Champions league runner-up, Hector Cuper’s Valencia. A dogged home-tie finished 0-0 with Bowyer picking up a suspension in the process, thus leaving him unavailable for the return leg. Many felt that it his presence that was most dearly missed in the midfield on that night in the Mestalla as Leeds were over run by an unstoppable Valencia side. The size of the moment got to the inexperienced Leeds players and an early, controversial goal from Juan Sanchez meant that they were always chasing the game thereafter. Valencia swept them aside in a crushing 3-0 victory and the European dream was over.

Although disappointing, Leeds fans had a lot to look forward to. The squad was still in its formative years and it had demonstrated that it had more than enough potential to succeed and compete at the highest level in the coming years. They had failed to re-qualify for the Champions League but further investment would lead to a renewed assault on the league title, and hopefully more Champions League football.

The 2001/02 season would be O’Leary’s last and it was the beginning of a dramatic and well-documented decline in fortunes for the Yorkshire club. A fantastic run of form saw them topping the league by the turn of the year but off-field issues derailed the campaign. An incident involving Lee Bowyer, Jonathan Woodgate and the assault of a student in Leeds city centre two years previous had finally come to court. Unexpectedly, the case served as a morale booster and brought the dressing room closer together. It was in fact David O’Leary’s decision to publish a book about the trial that plunged the club’s season into chaos. The board, staff and fans alike felt somewhat let down by O’Leary, it was felt that his decision to publish was wholly inappropriate and consequently he lost the dressing room. A dreadful period for the side commenced after a 3rd round FA Cup defeat to Cardiff at Ninian Park and Leeds did not taste victory for two months. Although seven wins from the final ten games of the season saw Leeds drag themselves into 5th place and the UEFA Cup, it was not enough to stop O’Leary from facing the axe. He had alienated himself among the fans, the players, and most importantly the board. In the eyes of the board, failing to qualify for the Champions league was insufficient after the level of investment made in the transfer market (by time he left £100m had been spent on transfers).

What followed was the darkest period in the club’s history. It soon became apparent that chasing success had come at a massive cost for Leeds United. Ridsdale had acquired a £60 million loan from the bank based on the belief that Leeds would be a constant presence in the Champions League, the business model meant that the debt would be payed for by elevated gate receipts and extra income from TV money. Essentially the hierarchy gambled the club’s future and lost. With the debt spiralling out of control selling the club’s talent became a necessity. The squad that O’Leary had expensively assembled was dismantled over the next couple of years and the players were sold to rival clubs for, at times, bargain prices: Ferdinand was sold to Manchester Utd for a British record fee and became the bedrock upon which Sir Alex Ferguson built his Champions League winning side; Kewell was sold to Liverpool for £5m where he also won a Champions League; Bowyer and Woodgate went to Newcastle, Paul Robinson to Tottenham, Dacourt went to Italy and so on, but the most painful transfer was that of Alan Smith to Manchester United. Alan Smith was the fans’ darling player from this generation and he had once famously stated he would never play for their bitter rivals.

Leeds United fans and football fans in general were never to know that 2001 would be the peak of success for David O’Leary and his Babies. Leeds United were so badly damaged that even Bob the Builder would not have been able to fix them. The following years would see Leeds United drop out of the Premiership in 2004 and three years later after further relegation they found themselves in the English game’s third tier. O’Leary’s future followed a similar trajectory, he spent three years without great acclaim at Aston Villa before being replaced, ironically, by Martin O’Neill, and his latest managerial feat was a fruitless period in the Middle East with Dubai based Al Ahli.

What if O’Leary had stayed? What if he had never written that book? What if they qualified for the Champions League in 2002? What if they had beat Valencia? What if the players had stayed together? What if Ridsdale had said no to some of the transfers? Terrible financial management from a reckless board, inflated transfer fees and misinformed decisions consigned this potentially world conquering Leeds side to the most sober page in the great big book of football history, the page of ‘what ifs’.