It was on May 23, 2007, when Italian icon Paolo Maldini wrote his name into the history books and secured his place in Champions League folklore.
The former AC Milan defender, almost two years to the day since being one of the victims of Liverpool's heroic comeback in Istanbul, got another stab at attempting to win his fifth European Cup. With the help of two Filippo Inzaghi goals, Maldini captained Milan to their seventh European Cup and his fifth, inflicting revenge on Liverpool in the process, winning 2-1 in Athens.
Despite winning the famous old trophy in 1989, 1990, 1994 and at Old Trafford in 2003, the 2007 success probably tasted the sweetest, such was the way Milan had capitulated in the final against the same opponent two years earlier and lost on penalties. Maldini climbed to the top of the podium and, surrounded by some of the most famous names to have ever played the game, including Alessandro Nesta, Andrea Pirlo, Cafu and Kaka, held the trophy aloft again.
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It marked his 25th and penultimate major trophy of his Milan career that spanned exactly a quarter of a century. He went down in history as one of the all-time greats, respected and loved by everyone, and as one of the greatest centre-backs to have ever played the game.
But had Sir Alex Ferguson had his way, Maldini could have been adding to his trophy collection in the red of Manchester United, instead of the famous red and black stripes of the Rossoneri. Such was the impression Maldini was making in Italy, both domestically and on the European stage, former boss Ferguson attempted to extract the now-54-year-old from the San Siro and bring him to Old Trafford.
At the time, believed to be around the mid '90s, Maldini was part of a Milan side that was littered with talent, featuring the likes of Massimo Ambrosini, Paolo Di Canio, Roberto Baggio and George Weah. They had dominated Europe in recent years and Maldini, who captained Milan from 1997 up until his retirement in 2009, was a vitally important cog.
Nevertheless, Ferguson, who, at that juncture, had not won the European Cup before, chanced his luck to try and bring one of Italian football's greatest sons to these shores. However, his hopes of adding him to his M16 talent pool were immediately quashed by Maldini's father, Cesare, who spent 12 years donning the famous red and black stripes himself, playing for Milan between 1954 and 1966.
Ferguson, speaking back in 2019, recalled: "I did try [to sign Maldini] but when I met his father he was quite formidable, I got a shake of the head. I remember him saying, 'my grandfather is Milan, my father is, I am Milan, my sons are Milan. Forget it.'"
As quickly as Ferguson had attempted to gauge an understanding of whether or not the legendary Italian defender would be interested in moving to England and playing for United, he quickly discovered that any hopes of it happening were dead in the water. Maldini had Milan in his blood and it was clear from his father's comments that he was going nowhere.
Maldini was a one-club man, joining Milan's youth system in 1978. He never once pulled on the shirt of another club until he retired in May 2009. The only time you ever saw Milan's all-time record appearance holder in anything but red and black was when he pulled on the famous blue of Italy, for whom he won 126 caps in an international career that spanned 14 years.
Ferguson, however, was not the only Premier League manager that attempted to convince Maldini to leave Milan. The late Luca Vialli, who was Chelsea manager at the time, called the now-Milan technical director, who was, in the eyes of so many, the greatest defender of his generation, to see if he would be interested in a move to Stamford Bridge. It was a possibility the seven-time Serie A winner thought about, but he knew his heart belonged in Milan.
"I had an offer from Manchester United, but I didn't speak directly to them," Maldini said, speaking in an interview with Jamie Carragher for the Mail in 2015. "Luca Vialli, when he was Chelsea manager, called me. That was in 1996.
"We'd had a very bad season. There was also something from Arsenal, but I never spoke to them directly. I would have said no, anyway.
"Vialli was a friend of mine and he was the only one who made me think. I had some problems with my team and the supporters at that time. I thought, just for one day, 'What if?' But then, no."
Just a week after Maldini had played his final game of what had been an illustrious and trophy-laden career on May 31, 2009, Milan's legendary No.3 received an offer to come to England again, this time in a coaching capacity. Chelsea, again, were the club seeking his services, but the Italian insisted he was not ready to make that step.
"The offer came only one week after my last game for Milan," he added. "I wasn't ready. I didn't want to move my family to London.
"I went there. I spoke to Mr [Roman] Abramovich. I spoke to Ray Wilkins, who I had played with at Milan. I don't know. I decided not to do it."
Maldini, prior to his retirement, had expressed that he never planned to step into the world of coaching. He took a step back from football until August 2018, at which point he returned to Milan to become their sporting strategy & development director. Less than 12 months later, he was promoted to technical director.
But you do wonder had Ferguson struck lucky and successfully tempted one of football's all-time greats to move to England how his career would have developed. He would have, undoubtedly, become a mainstay in Ferguson's plans for years, rubbing shoulders with some of United's greats of the past, such as Paul Scholes, David Beckham, Ryan Giggs and countless others.
United, eventually, did stumble across a collection of centre-backs during Ferguson's time that served the club so well, such as the likes of Jaap Stam, Rio Ferdinand and Nemanja Vidic. Maldini, though, would have been different gravy. He was one of a kind and Ferguson plucked up the courage to tempt him, even if his efforts collapsed imminently.
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