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Il Capitano.

January 20th 1985. On the day Ronald Reagan re-took the oath of office for his second term as US President, a young Italian called Paolo Maldini joined the family business. At this stage Paolo was known as ‘Cesare’s son’. Some teammates sneered that Paolo was ‘recommendato’ (connected) when he arrived as a boy at AC Milan in 1978, the club where his father Cesare Maldini played for 12 seasons. Maldini senior captained Milan when they became the first Italian side to ever lift the European Cup in 1963 and Cesare managed them in the early 70s too.

Big boots to fill, and boots were an early problem for Paolo. Italy had been hit by a record freeze in 1985 with temperatures plummeting to an Arctic -20 in Florence and -13 in Udine up in the North East of the country where Paolo was on the bench for Milan’s away match against Udinese. He didn’t have the right boots for a snowy pitch. Luckily, a fellow sub that day sorted him out with a pair – grazie Ray Wilkins (even if they were two sizes too small). Another Englishman came to the rescue that day too. Striker Mark Hateley salvaged a point for Milan with an equaliser after 63 minutes. It was Hateley’s sixth of the season nudging him one ahead of the shy and unassuming Diego Maradona who was midway through his first season in Italy. Hateley rescued a point at home to Fiorentina the following week too, but didn’t score again in the league again that season.

The game would be Paolo’s only first team appearance of the 1984-85 season, and one of his only appearances ever at right-back. Though right-back was his natural position, the formidable Mauro Tassotti had made that slot his own – but a vacancy arose on the other side and Paolo gabbed the No.3 shirt, wearing it for 24 seasons. The No.3 is now retired at Milan, the only event in which it could be worn again is if one of Paolo’s sons progresses into the Milan first team and chooses it. His eldest, Christian (born the day Italy lost 2-1 to Czech Republic at Euro ‘96) got as far as Milan U-19s but left permanently in 2016 and is currently plying his trade as a left-sided centre-back for Pro Sesto in Serie C. More interestingly, Paolo’s second son Daniel (who went viral aged five when footage of him executing a slide tackle attempt on Clarence Seedorf hit the internet) made his Rossoneri First Team debut in February 2020 scoring in a friendly against Monza. But, playing as a winger or AMC, he’s unlikely to ever pull on the No.3.

“It’s about time,” laughed Paolo speaking to James Horncastle at The Athletic in 2020 about his youngest son. “Our family has spent a lifetime chasing after other players. Now we have someone who they’re going to have to chase. I can assure you that it’s harder running after the ball than to be chased with it.”

The number three would man-mark Paolo throughout his career. He scored three goals in his entire Champions League career, conceded three painful ones against Liverpool in the famous 2005 final and in the same match became the oldest player to score in European Cup history, aged 36 years and 333 days. His greatest season began in 1993: Milan won Serie A, the Champions League (a trophy he would lift across three different decades) and Paolo finished 93-94 by playing in a World Cup Final with Italy. All the negative stereotypes of Italian defenders – niggling, pinching, play acting – didn’t apply to Paolo, he retired with only three red cards to his name.

Paolo’s playing style and career could have sprung from the pages of a Marvel comic. I was tempted to dedicate this entire article to his incredible hair. Physically he was the perfect storm of a defender: 6ft 2in with rapid pace and an unmatched footballing IQ that allowed him to see play multiple moves ahead. He introduced football to a new level of defending, and did so with glamour and style, if not necessarily technique. “If I have to make a tackle then I have already made a mistake”, he famously stated, presumably before sprinting off into the night to fight crime and rescue kittens from burning buildings. He was combative, elegant and ahead of his time in terms of fitness and lifestyle, playing beyond his 40th birthday.

Having played over 1,000 competitive games for Milan and Italy, it’s not easy to pinpoint peak Maldini but the 1994 Champions League Final could be close. Not least for the circumstances that led to the game. Milan faced one of the all-time great teams: Barcelona managed by Johan Cruyff, spearheaded in attack by Romario and Hristo Stoichkov, bolstered in defence by Miguel Nadal and Ronald Koeman both of whom were protected by a young DM called Pep Guardiola. Milan went into the game without first choice centre-backs Franco Baresi or Alessandro Costacurta, so Maldini switched to central defence. A completely new role for the 25-year-old. Barcelona didn’t get a kick and Milan won 4-0.

Off the pitch Maldini often prefers to talk about anything but football. His house has no football memorabilia on display whatsoever. He loves boxing and reached such a high level playing tennis in retirement he actually qualified for a doubles event at an ATP Challenger tournament in 2017 aged 49. How much would you give for just five percent of Maldini’s aura?

Alex Ferguson marvelled how he once watched him across two legs of a Champions League semi-final against Bayern Munich without seeing him slide once. “When I think of the current generation,” said Ferguson, “Lionel Messi is top-level, Zinedine Zidane was brilliant too but, without a doubt, Paolo Maldini has been my favourite. He has a wonderful presence, competitive spirit, athleticism, and although not the world’s greatest technically, he has influenced all the Milan teams during his wonderfully successful era.”

Naturally, Ferguson tried to sign Maldini. He wasn’t the only one. “Luca Vialli, when he was Chelsea manager, called me.” Paolo explained to Jamie Carragher in an interview that took place at Maldini’s home to mark the tenth anniversary of Istanbul. “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.”

Paolo was, and still is, very much his own man. An example of this fierce independent streak can be found in his relationship with the Milan hierarchy and powerful ultras of the Curva Sud. “He always kept a certain distance,” explained Italian football expert Gabrielle Marcotti speaking on Golazzo: The Totally Italian Football Show podcast. “He was always very grateful for what Silvio Berlusconi did for the club and the ultras as well, but on the day he played his last game for Milan there was a portion of ultras, they weren’t speaking for everybody, but they put up a banner that said: ‘On the pitch you are unquestionably the greatest ever, off the pitch, there’s only one captain, and it’s Baresi.’ Possibly because Baresi never had that independent streak.” At the post-game press conference Maldini declared: “I’m proud to be nothing like them.”

The Milan ultras should have been thanking the football gods that the careers of two of the greatest defenders of all-time overlapped at their club. Maldini the beauty, Baresi the beast. They played 296 Serie A games together in which Milan kept a frankly staggering 145 clean sheets. Utterly stingy.

Illustration by Jonathan Bruns / @jonathan_bruns

In ironic contrast, on the occasion of Maldini’s last Derby della Madonnina, Inter Milan supporters unfurled a banner celebrating him. ‘Per 20 anni nostro rivale, ma nella vita sempre leale’ (For 20 years our opponent, but in life always loyal). “On a human level, I think it’s one of the most satisfying moments I’ve ever experienced,” Maldini would say.

His fierce loyalty ties him to Milan and Italy. In Europe, it would be difficult for Maldini to work anywhere other than AC or with the Italian national team, such is his association with the Rossoneri and Azzurri. He has no desire to manage, describing the dugout as “the job which unites all the things that I don’t like about football together”. He turned down a chance to reunite with his former teammate Carlo Ancelotti as a coach at Chelsea after he finished playing. Then, in 2015, he co-founded Miami FC who currently play in the USL Championship. This is the second tier of the American soccer league where the only chance of promotion to MLS is if a club can afford the multimillion dollar franchise fee. Maldini’s Miami see themselves more as a community asset compared to the glitz and glamour of city neighbours Inter Miami CF, co-owned by another of Paolo’s former teammates, David Beckham, who debuted his ‘Inter Miami CF’ in MLS in March 2020.

In 2016 Maldini interviewed for the position of Technical Director at Milan but surprisingly rejected an offer for the only job he ever really wanted. The reason? He didn’t believe the blueprint he was shown was the basis for a winning team. That must have been hard. To Maldini, this is more than a profession. It’s personal. It’s his team, his life. The Chinese-backed owners responded with a statement: “We regret Paolo Maldini’s decision regarding our proposal because we firmly believe that he will soon realise how much of a winning project ours is for Milan.”

Maldini was proved right. Milan finished sixth in both 2017 and 2018 with the second highest wage bill in Serie A. When owner Li Yonghong defaulted on a €32m loan to help Milan resolve a problem relating to UEFA’s financial fair play regulations in July 2018, Elliott Management Corporation repossessed Milan. Within two months Maldini had taken up the sporting strategy and development director role he rejected two years previous. That independent streak had served him well.

He has a big job on his hands. Working alongside former Arsenal CEO Ivan Gazidis, Maldini sits on the club’s executive team as technical director flanked by head of football operations Hendrik Almstadt, sporting director Ricky Massara, a 33-year-old chief scout called Geoffrey Moncada and a presence from ownership, hedge fund, Elliott Management.

“The financial position was such that we ultimately had to accept a ban on European competition,” explained Gazidis, speaking to The Athletic in September 2020. Milan found themselves 21st in the football club rich list, turning over just €6 million more than Leicester City. There is serious catching up to do. The gap between Rossoneri revenues and the wealthiest club, Barcelona, is €634.5 million. Premier League TV contracts dwarf Italy’s, Bundesliga clubs rebuilt their infrastructure ahead of the 2006 World Cup (something Italian clubs should have done before Italia ‘90) while Lionel Messi and Cristiano Ronaldo have turbo charged La Liga. Serie A is behind.

Football teams have cycles. Teams build, dominate, then players move on and replacing established, world class talent isn’t easy. Liverpool, Real Madrid, Man. United and Bayern Munich have all ebbed and flowed. AC Milan are no different. It’s been 10 years since they last won the Scudetto, six since they last appeared in the Champions League. Those stats will hurt Maldini because he knows how great they can be. He knows what it takes and how it feels, because he lived and breathed it for 24 years and has the aching ankles to prove it. Milan kept their cycle going for 25 years, and Maldini was the heartbeat. A once in a generation team, led by a once in a lifetime human.

MALDINI: THE NUMBERS

Most appearances for an Italian club 902
126 caps for Italy
25 trophies
7 Serie A titles
5 European Cups / Champions Leagues
6 domestic Italian Cups
4 UEFA Super Cups
2 Intercontinental Cups
1 FIFA Club World Cup
Youngest ever Milan player aged 16 years and 208 days
Oldest player to score in a Champions League Final aged 36 years and 333 days
Fastest goal in a Champions League Final 50 seconds
8
Champions League Final appearances
Most competitive appearances in Europe 168
Most World Cup appearances for Italy 23
Most minutes played at World Cups 2,216
Longest serving Milan player 24 years and 132 days