Cristiano Ronaldo the Chelsea legend?! Agent reveals Blues rejected chance to sign CR7 for just €3.5m before Man Utd pounced

Near misses on the transfer front are common in modern football, with there no telling what players of obvious potential will go on to become. While they can often illuminate the youth ranks, or enjoy a bright start to their senior careers, longevity can never be guaranteed.

With that in mind, clubs around the world boast tales of near misses and what could have been. Chelsea fall into that camp, with questions probably still being asked in west London of how they allowed Ronaldo to slip the net.

He was a fleet-footed winger on Sporting’s books when former player turned agent Silkman attempted to broker a deal with the Blues in 2003. His pleas fell on deaf ears, with Ronaldo - who is now a five-time Ballon d’Or winner and still going strong at 40 years of age - ultimately making his way to Manchester a matter of weeks later.

Silkman - who represented the likes of Wimbledon, Manchester City and Leyton Orient in his playing days - has told The Telegraph of one particular agreement that he failed to get over the line: “I did a deal with [Ronaldo’s agent] Jorge Mendes. But Chelsea said no. Cristiano Ronaldo was €3.5m and the deal was everything over that was split 50-50 with the club. He played against Man United pre-season, ruined them and straight after the game they paid €11.5m and Jorge must have stuck four million in his pocket. Good luck to him but I was gutted!”

Silkman went on to say of Ronaldo, who continues to illuminate the global game with Al-Nassr and Portugal: “If Cristiano Ronaldo was coming into the game today, he would do well to get signed by Barnsley because they’d be saying to him ‘what are you doing? All these stepovers and tricks and flicks? Pass the ball!’

“Coaches don’t want teams to make a mistake. I’ve watched a lot of young coaches. To say it’s crap is an understatement. What you hear is, ‘pass, pass, pass’. You never hear someone say, ‘Take him on, drop the shoulder, do a trick’.”

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United phased tricks out of Ronaldo’s game during his time at Old Trafford, with his transformation into a free-scoring, Golden Ball-winning frontman being completed at the so-called ‘Theatre of Dreams’.

Chelsea’s loss was most definitely the Red Devils’ gain, with Ronaldo going on to make history and rewrite the record books with United, Real Madrid and Juventus. He is expected to grace another World Cup next summer and is giving little thought to retirement.

Discussing some other big names that he almost took down a different path to the one that made them famous, Silkman told The Telegraph: “Thierry Henry. Could have got him for £500,000 when he was a kid at Monaco as it was only compensation. I tried to get Harry [Redknapp] to buy him at West Ham and he scored a hat-trick in the game and Harry was convinced something had to be wrong with him. He stayed, signed a contract, went to Juventus and they messed up and played him on the left wing. And then went to Arsenal.”

He added on another Ballon d’Or winner who did pass through Chelsea and City after becoming a global superstar with AC Milan: “Then there was George Weah. I was bringing him on a free. No one wanted him. Five different clubs. They also said 'he can’t be any good if he’s free'.”

Chelsea will be cursing their luck at having passed on Ronaldo. He has worked with fellow countryman Jose Mourinho over the course of his remarkable career, during their time together in Madrid, but they could have chased down Premier League titles together from 2004 had the Blues listened to Silkman’s advice.