Did Real Madrid dream of signing Lionel Messi alongside Cristiano Ronaldo? Former president explains why transfer to unite GOATs was ‘impossible’

Calderon was the man behind Ronaldo's arrival at Madrid in 2009. At that time, they broke the transfer record by buying the Portuguese player from Manchester United for a fee of £80 million ($107m). While Ronaldo was always the primary target for Madrid, the shadow of his eternal rival, Messi, loomed large over Spanish football during his era-defining spell at Barcelona.

Calderon admitted that he dreamed of uniting the two at one club, which would be the pinnacle of sporting achievement. However, facing the realities of rivalry makes such a dream almost impossible, given the historically bitter rift between Spain's two biggest clubs.

Speaking about the prospect of a sensational swoop for the Argentine maestro, Calderon was candid about the roadblocks in place. The political and emotional ties to Catalonia meant that any approach from Madrid would have been met with immediate rejection, keeping the two icons on opposite sides for the duration of their peaks.

"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."

While Messi remained out of reach, the pursuit of Ronaldo was an exhausting saga that spanned several seasons. Calderon insists that the credit for the move belongs to the stature of the club rather than personal negotiation skills, noting that the forward was determined to leave Old Trafford for the Bernabeu despite Sir Alex Ferguson's resistance.

"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 seize the opportunity to sign him with both hands."

Despite the unprecedented success Ronaldo achieved in a white shirt, Calderon believes the eventual separation in 2018 was a mistake for everyone involved. The relationship between the Portuguese star and incumbent president Florentino Perez reportedly cooled, eventually leading to a record-breaking move to Juventus that failed to replicate the heights of his time in Spain.

"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."