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The football world has long debated who stands as the greatest player of all time, but there was once a period when Real Madrid seemed to ponder the dream of uniting Lionel Messi and Cristiano Ronaldo under one roof. Former Real Madrid president Ramon Calderon has now spoken about whether the Spanish giants ever seriously believed such a historic partnership could happen at the Santiago Bernabeu.

The dream of the ultimate duo

It was Calderon who orchestrated Ronaldo’s move to Real Madrid back in 2009, a deal that shattered the world transfer record at the time. The Portuguese superstar was signed from Manchester United for £80 million ($107 million). While Ronaldo was always the club’s primary target, his fierce rival Messi dominated Spanish football during his glittering years at Barcelona, leaving Madrid constantly in his shadow.

Calderon has confessed that he once imagined bringing the two superstars together in one team — something that would have been the pinnacle of footballing achievement. However, he acknowledged that the deep-rooted rivalry between Real Madrid and Barcelona made such a dream practically impossible, given the historical animosity between the two clubs.

Why Messi to Real Madrid could never happen

Reflecting on whether there was ever a realistic chance of signing the Argentine legend, Calderon was upfront about the insurmountable barriers. The emotional and political ties Messi had with Catalonia meant that any approach from Madrid would have been instantly dismissed, ensuring that both icons stayed loyal to their respective sides during their prime years.

“I would have loved it, but it was impossible because Messi was at Barcelona and they would never have let him leave unless he took the initiative, like Cristiano did at Manchester United,” Calderon told A BOLA. “But he was happy at Barca and therefore there was no possibility. It was a shame because bringing together the two best players in the world on the same team would have been fantastic.”

The long pursuit of Ronaldo

While Messi was never a feasible target, Real Madrid’s chase for Ronaldo was a tough negotiation that stretched across two years. Calderon emphasized that the signing was ultimately down to the club’s immense reputation rather than individual persuasion skills. He noted that Ronaldo was determined to leave Old Trafford for Madrid, even though Sir Alex Ferguson tried hard to keep him in England.

“We were in negotiations for two years. Manchester United, naturally, didn’t want him to leave, but the player wanted to go,” Calderon explained. “It’s well known that footballers like Cristiano end up going where they really want to go; it’s impossible to hold them against their will. I insist, I was there and, as anyone else would have done, I seized the opportunity. At that moment, he was the best player in the world alongside Messi, and therefore, the most logical thing to do was to sign him with both hands.”

The departure and life after Madrid

Even though Ronaldo enjoyed extraordinary success with Real Madrid, Calderon believes that his departure in 2018 was a misstep for both the player and the club. His relationship with current president Florentino Perez reportedly soured over time, culminating in a €100 million transfer to Juventus — a move that, according to Calderon, never truly matched the glory of his Madrid years.

“I believe it was a mistake on both sides,” Calderon concluded. “Certainly the relationship wasn’t good from the beginning, then, over time, it deteriorated towards the end of his time here. I believe the president didn’t think anyone would be able to pay 100 million euros, but yes, there was a club willing to do it, and then he had no other option but to accept the player’s departure. The player never fully adapted to any club outside of Real Madrid, and Real Madrid was difficult because it’s impossible to find someone like Cristiano.”