Raul may be Real Madrid’s biggest legend – but he could have become a Tottenham hero had it not been for club chairman Daniel Levy.
The 47-year-old is regarded as one of the finest strikers of his generation following a glittering 21-year professional career.
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No player in Los Blancos‘ history has featured more times for the club than Raul, who played in 741 matches from 1994-2010.
He is also third in Real’s all-time scoring charts with 323 strikes – with only Cristiano Ronaldo [450] and Karim Benzema [354] finding the back of the net on more occasions.
His knack in front of goal failed to wane towards the end of his Madrid career, banging in 23 times in all competitions during the 2007/08 season.
Incidentally, that campaign saw Tottenham end their nine-year trophy drought by lifting the League Cup at Chelsea‘s expense under the tutelage of Juande Ramos.
That trophy – Spurs‘ only piece of silverware this century – was supposed to be the springboard for continued success.
The 2008 summer window saw the north London outfit bring in midfielder Luka Modric and striker Roman Pavlyuchenko.
And Raul has revealed he held talks with Ramos to become their next high-profile star with the 2009 winter transfer window on the horizon.
Spurs were in the market for a new centre-forward having sold fan favourite Dimitar Berbatov to Manchester United.
And Raul – then 31 – was open for a new challenge in England, where he would have competed with Pavlyuchenko, Darren Bent and Robbie Keane up top.
However, having guided Spurs to their worst ever start to a league campaign after picking up just two points from their opening eight games, Levy axed Ramos after 12 months in the dugout, with Harry Redknapp swiftly replacing him.
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As luck would have it, Ramos, who shared the same agent as Raul, was then snapped up by Real in December 2008 – winning ten of his first 12 matches.
He was lauded by Raul for turning around Real’s fortunes, while the legendary striker also divulged just how close he came to joining Spurs.
Speaking to Digital Plus in February 2009, Raul said: “Four months ago, Juande and I had a meal with Gines Carvajal, who is our agent and a friend of mine.
“They called me because I like English football and I wanted Juande to tell me about his experience of Tottenham and of The Premier League.
“He is a football man and speaking with him is a pleasure.
“A chain of events meant that he was sacked and then Madrid were interested in him.
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“The fact that we share the same agent led to unfortunate interpretations.
“Juande is a winning coach and he has proved that he is good enough to manage Real Madrid.”
When Raul decided to leave Real in 2010, Tottenham were touted as as one of his destinations.
Fuelling rumours, Raul stated at the time: “My future lies in Germany or England.”
In the end, he decided to make the move to join Schalke on a free transfer
Raul eventually remained at Real until 2010 – scoring 40 goals in 98 games – helping them lift both the DFB-Pokal and the German Super Cup.
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Moves to Qatar and America followed at Al Sadd and New York Cosmos, before he decided to hang up his boots in 2015.
A true legend of the game, Raul has left a lasting legacy during his lengthy stay the Bernabeu.
He was part of the Real squad that scooped three Champions League crowns in five years.
The 102-cap Spain international scored in both the 2000 and 2002 final victories over Valencia and Bayer Leverkusen respectively.
He also won six LaLiga titles – winning the Pichichi Trophy in both 1999 and 2001 for being the division’s leading scorer.
But the question mark will always remain over whether he would have sealed his place in Spurs folklore had Ramos have been given more time by the board.
