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“Per 20 anni nostro rivale, ma nella vita sempre leale,” the banner unfurled by Inter’s ultras read ahead of Paolo Maldini’s final Derby della Madonnina. “For 20 years our opponent, but in life, forever loyal.”
Nothing could better encapsulate the Rossoneri icon’s standing at San Siro quite like supporters of his club’s greatest rivals dothing their metaphorical cap.
For 25 seasons, Maldini was Mr Milan. His 647 Serie A appearances were a record until Juventus keeper Gianluigi Buffon surpassed him last season. In a club-record 902 outings for Milan, Maldini lifted the UEFA Champions League (5), Serie A (7), the Coppa Italia, Supercoppa Italiana (5), European Super Cup (5), Intercontinental Cup (2) and FIFA Club World Cup.
What makes Maldini’s stunning career with the Rossoneri all the more remarkable is that his father was already a bona fide Milan legend. Cesare was part of the great Milan side which won four Scudetti between 1955 and 1962. Quite a legacy to live up to. Yet it was clear from the outset that the new kid on the block would have little difficulty matching up to his old man’s achievements.
Milan and Italy legend Franco Baresi was still playing when young Paolo burst onto the scene and recalled his emergence: “He was very young, so I tried to give him some advice. But he needed very little, as he was already a great player.”
A cool, calm and stylish defender who was predominantly a left-back, Maldini could also play inside with minimal fuss as a left-sided centre-back. If defending is an art, the former Milan No.3 was a Michelangelo, Raphael or Caravaggio.
In January 1985 and aged just 16, Maldini made his first appearance for the Rossoneri, replacing the injured Sergio Battistini in a draw with Udinese. The following season he was promoted to the senior squad on a full-time basis, although he frequently ended up playing right-back despite being handed the No.3 jersey his father had worn before him. Eventually, though, Maldini made the switch to the left-hand side and never looked back.
Part of an iconic back four along with Mauro Tassotti, Alessandro Costacurta and Baresi, Milan had not won the Scudetto since 1979 when Maldini got his hands on the first of seven league titles in 1987/88. Complemented by the iconic Dutch trio of Ruud Gullit, Frank Rijkaard and Marco van Basten, as well as homegrown midfield talents Carlo Ancelotti, Roberto Donadoni and Demetrio Abertini, Milan became known as ‘The Immortals’.
Helping cement their legacy was the 1994 European Cup final win over Johann Cruyff’s Barcelona side in Athens. The so-called ‘Dream Team’, featuring Andoni Zubizaretta, Pep Guardiola, Ronald Koeman, Romario, Hristo Stoichkov and Txiki Begiristain, were thumped 4-0 by Fabio Capello’s Rossoneri. It was the first of five European Cups for Maldini who was lauded for his role in a era-defining win.
Remarkably, by 1995 Maldini was already racking up his 300th Serie A performance, a measure of his remarkable consistency and availability. In a career which spanned more than 1,000 professional appearances, he was sent off just three times – testament to his impeccable timing in the challenge and peerless reading of the game in front of him.
The summer of 1997 signalled a time of change for Milan with iconic duo Tassotti and Baresi both calling it a day. Maldini was named captain and led his side to the Coppa Italia final in his first season with the armband, only to be beaten by Lazio. On the whole, these were lean times for the Rossoneri who went through six managerial changes between the end of of Capello’s second spell in 1996 and the appointment of Ancelotti in 2001 – one of which saw Maldini Snr, in tandem with former team-mate Tassotti, handed the reins.
By the end of 1998/99 Milan were champions of Italy once more, but success could not be sustained. Milan’s fortunes improved dramatically under Ancelotti. With Cafu, Alessandro Nesta, Jaap Stam and Costacurta for defensive peers, Maldini helped form another intimidating backline which was to prove the backbone of the club’s success over the next few years.
Between 2003 and 2007, Milan won seven trophies under Maldini’s leadership, even getting revenge on Liverpool two years after the ‘Miracle of Istanbul’. In doing so he became the oldest captain to lift the Champions League at 38. Two years prior he had scored the fastest goal in European Cup final history, netting after just 51 seconds against Rafa Benitez’s side. But this was the end of Milan’s period of dominance in Italy with rivals Inter and, latterly, Juventus taking over. The Rossoneri have not competed in the Champions League since 2014 and haven’t gone further than the quarter-finals since Maldini retired in 2009.
Having already delayed his retirement by a year in June 2008, Maldini called time on a glittering career on May 31 2009, after helping Milan secure Champions League qualification once more by finishing third. The Rossoneri honoured ‘Il Capitano’ by retiring his No.3 jersey, though it could be worn again if either of his sons play for the club. Earlier in 2020, Daniel, a winger, made his senior debut to keep the dream of three generations of Maldinis wearing the iconic red and black stripes alive.
After almost a decade away from the frontline, Maldini rejoined Milan in August 2018, taking up the position of sporting strategy and development director. In June last year he was promoted to technical director, working closely with the first-team coach to recruit players. An iconic figure of the club’s recent past, Maldini is now working to steer his beloved side back towards happier times too.