Engineering an exit in football is never easy, no matter what your status in the game.
So when Cristiano Ronaldo, Sir Alex Ferguson and Jorge Mendes are involved in the matter, it's rather a big deal. For the last four months, Manchester United legend Ronaldo has been attempting to leave Old Trafford, but he's yet to get his wish after the Red Devils were reluctant to offload him in the summer transfer window.
Super-agent Mendes is still tasked with making sure his megastar client's gets his way soon enough, though, just as he was in 2008 when he was dealing with Ferguson, then United boss as a opposed to his advisory role these days. 14 years ago, during Ronaldo's first and more harmonious stint in Manchester, the No.7 wanted to join Spanish giants Real Madrid, having just won the Champions League off the back of three successive Premier League titles.
Mendes and Ferguson had, of course, dealt with one another plenty of times prior to Ronaldo's insistence to depart in 2008, but the agent and manager strengthened their relationship when they ended up on the exact same page regarding the forward's future.
Back in 2017, Ferguson praised the "amazing" Mendes for his sacrificing personal gain in order to convince Ronaldo to stay at Old Trafford for one more year and the betterment of his career. "At the time, [Ramon] Calderon was running for Real Madrid's presidency and used Cristiano as a reason to vote for him, which was unseemly of him," the Scot told France Football.
"I took the plane to Lisbon to meet Cristiano in [Portugal manager] Carlos Queiroz's house. I told him, 'You are not leaving this year. I do not want to sell you to Calderon. But if you play well, you will leave later'.
"Jorge Mendes was amazing. He did not want Cristiano to leave. He felt that he was not ready. He put his financial interests aside as well as those of the player – all that money he could have won – for Cristiano's career, including that amazing 2008-2009 season.
"He knew that I would not go back on my promise. His concentration and work ethic were marvellous. In 2009, Florentino Perez became president of Real, which made it easier for us to work with him concerning his transfer."
There's certainly a mutual respect between Ferguson and Mendes, with the agent always speaking kindly of Ronaldo's former manager in public. "It's completely impossible to find someone like Sir Alex Ferguson," Mendes told BBC Sport. "He's a god, he's a genius and to find a genius is very difficult."
More than two decades ago, when he was first making waves on the financial side of the game, the Portuguese went to great lengths to meet Ferguson for the first time. Revealed in the new book, 'Messi vs. Ronaldo: One Rivalry, Two GOATs, and the Era That Remade the World's Game', Mendes was unfortunately involved in a car crash the night before he was due to fly to the UK.
Having been saved alongside his girlfriend thanks to the vehicle's airbags, he refused to be seen by doctors and discharged himself from hospital, despite skin from his ear being excruciatingly torn off after the car smashed into a guardrail. Mendes, who'd self-medicated with bandages, got a lift straight to the airport and incredibly, he managed to catch his flight.
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As relayed by The Mail, a passage in the book reads: 'Mendes made it. He even positioned himself at the table in such a way that Ferguson wouldn’t see the unsightly mess that used to be his ear. It was a heroic effort, but to no avail. Mendes, his ear throbbing and heavily bandaged, uttered no more than four words the entire meeting'.
The two were reunited this July when Ronaldo returned to United's Carrington training complex for the first time since May to hold showdown talks over his future. Although the 37-year-old had made it clear that he wanted to leave, it's obvious that both he and Mendes wouldn't take any enjoyment in tarnishing their respective relationships with Ferguson to force a move.
The ex-Red Devils manager remains a member of the club's footballing advisory board, with his opinion on Ronaldo's latest saga likely to hold plenty of weight at Old Trafford. After weeks of debate and drama surrounding his future, the expectation is that United would allow their iconic player to depart after the World Cup in January, given his struggles under new boss Erik ten Hag - and that's perhaps the best outcome for all parties.