Five world class players David O’Leary’s Leeds United almost signed

Down the years Leeds United have come close to signing hundreds of players, but for one reason or another the transfers have never quite materialised.

In this article we look at the era of David O’Leary when the former Whites’ boss was given a big budget to play with to make Leeds title and European contenders.

As we know things didn’t turn out very well, but it could have been very different if they would have got one of these five major transfers over the line…

Roy Keane

Yes, really! At the start of the century when Leeds were spending big chasing glory the club got wind of a fall out between Manchester United captain Roy Keane and manager Alex Ferguson. Keane told Irish TV in 2019: “I remember I fell out with Alex Ferguson and he was going to sell me. Leeds were in for me at the time and things got really heated. But I was a really important asset to Man Utd then and I stayed.” If that move had happened, it would have undoubtedly changed the course of history, to what extent though, we’ll never know!

Frank Lampard

At the same time Leeds were eyeing Keane, Frank Lampard was also on their radar. Former Chelsea midfielder Alan Hudson revealed in his book how Lampard, and not Seth Johnson, would have moved to Elland Road but for his intervention.

“The move [to Chelsea] wouldn’t have happened without me,” Hudson claimed. “A few weeks before he (Lampard) was going to join Leeds and his old man called me out of the blue for my opinion. I told him you can’t go to Leeds – they had three or four players who were troublemakers, in the news for fighting in nightclubs, and I knew that Frank wouldn’t fit in with that. I knew he was ambitious from when he was a boy, he was always a grafter, and I told Frank senior that he had to go to Chelsea. Next thing you know … It’s amazing how it all turned it out.”

Mark van Bommel

Leeds went all-out for Dutch midfield maestro Mark van Bommel at the start of the century. Regarded as one of the world’s best defensive midfielders at the time, PSV Eindhoven played hard ball on their captain and O’Leary was forced to look elsewhere. Van Bommel, who later joined Barcelona, was not keen on the move to Elland Road stating: “Leeds are not big enough for me. I want a team who will always be in the Champions League,” he told The Sun.

Ruud van Nistelrooy

It wasn’t just Van Bommel Leeds tried to sign from PSV – Incredibly they had Ruud Van Nistelrooy on their radar well before Manchester United did. Despite having an array of top class strikers to choose from, O’Leary wanted to add more goals and he scouted the Dutch striker for a whole season. However, with the likes of Mark Viduka, Alan Smith, Robbie Fowler and Robbie Keane at his disposal, the Irish manager opted against pushing for the transfer. Man Utd later paid £19 million to sign van Nisterooy and he became a Premier League great.

Kieron Dyer

Going back slightly to 1999 and O’Leary was attempting to add more youth to the Premier League’s most exciting side. Aged just 20 and having impressed at Ipswich, Kieron Dyer was involved in a bidding war between Leeds and Newcastle. Despite his speed and style seemingly suiting O’Leary’s youthful team, he opted to join the Toon. “There was always something about me and Leeds,” Dyer said in an interview with the Newcastle Chronicle in 2013. “There was always plenty of spice. Leeds tried to sign me at the same time as Newcastle. That made it a game I really relished. They were my favourite team to play against. I always did well against them.”

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