14 June 1973: David O’Leary signed for Arsenal.

He signed as an apprentice for Arsenal in 1973 and played for the reserves from the age of 16, playing his first game for the first team on 16 August 1975, aged 17.  Twenty years later, on 17 May 1993 David O’Leary played his farewell game v Manchester United.

His first major honour was the FA Cup – playing in the win over Manchester United although he also played in the defeats in the other two cup finals of the era, and the Cup Winners Cup final of 1980.

By the age of 26 he had played over 400 times for the club, and then overtook the record for the most games for the club – reaching 622 (Armstrong held the record before that).

It was the partnership of Bould and Adams that finally dislodged him, but he did win the league with Arsenal in 1989 and 1991, and played in the double-winning side of 1993, often as a sub. Then he was given a free transfer to Leeds after 19 years with Arsenal, and played regularly for them.  He retired from football as a player aged 37, after suffering an Achilles injury.

David O’Leary had a more difficult relationship with Ireland, missing games through being dropped by Charlton, and for refusing to give up a family holiday when he was called up at the last moment.

After life as a player, O’Leary went into management as assistant to George Graham at Leeds.  After Graham went to Tottenham, O’Leary became Leeds manager and in 1999 took them to fourth in the Premier League.In 2000 Leeds were knocked out of the Uefa cup in the semi-final and finished third in the league, and it seemed that Graham knew what he was doing when he took O’Leary into management as astoundingly Leeds got to the semi-finals of the Champions League. 

But Leeds were in real trouble – as the words “Peter Ridsdale” took on a special meaning.  Gambling on the fact that Leeds would play in the Champions League again, he had borrowed £60m for O’Leary to buy new players.
But Leeds didn’t get into the Champions League for 2001/2, nor the next season. 

Meanwhile, O’Leary wrote or had ghosted a book “Leeds United on Trial” – about the activities of some players in the town centre, and their subsequent trial – while at the same time spending what was then an amazing £100m on players over a four year period.

Indeed three facts can be noted. O’Leary didn’t win a trophy at Leeds, he never seemed to ask where on earth the £100m had come from, and he was beyond doubt disloyal to the club in his writing of the book.

O’Leary left, and in 2004 Leeds were relegated to division three with £80m debt.  Meanwhile, O’Leary became manager of Aston Villa and by 2005 was spending considerable sums of money on players, but only finished two places from relegation.  He left in 2006.  His next management job was in the UAE from July 2010 to April 2011 when he was sacked having won six of the 15 games his team had played.

However, despite his later activities he is quite rightly remembered as a true servant of Arsenal, and a truly remarkable player.