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Words: Owen Blackhurst
Images: Getty, unless otherwise stated

Originally published as our Issue 22 cover story, this is The Chronicles of Paolo Maldini, a six-chapter celebration of a man with Rossoneri in his veins...

Part 01—Il Figlio (The Son)It was cold in Udine on January 20th 1985. In fact, it’s always cold in Udine in January; the positioning of the city high in Italy’s northeast, with the Alps to the near north, the Slovenian border 30 minutes to the east, and the Adriatic Sea visible to the south, leaving it open to all types of meteorological variables. But on that day, it was especially cold—freezing or thereabouts. You could see it on the pitch—recently cleared of snow, slick with mud and ice. The paint used to mark the lines barely hanging on without a blade of grass to cling to. It was there in the faces of the crowd, spidery veins pulsing purple, mouths belching out unfiltered cigarette smoke and cold breath, the blue of the former meeting the grey of the latter and drifting towards the substitutes, themselves wrapped up in blankets and rubbing gloved hands together.Milan, behind 1–0 at the break, made a single injury-enforced substitution. On to replace Sergio Battistini is a tall, slender, 16-year-old with piercing blue eyes. He takes his place at right back wearing number 14. For now, he’s a curiosity. Variations of the same question floating into the ether.

“Is that Cesare Maldini’s boy?”


All things considered, Paolo Maldini is an anomaly. The progeny of world-class footballers rarely make it as top professionals, let alone surpass the achievements of their father. Kasper Schmeichel has won a Premier League and an FA Cup without ever getting close to his dad. And even though clips of Kai Rooney and Cristiano Jr scoring outrageous goals for Manchester United youth teams are increasingly regular, the offspring of the very best footballers either end up as a travelling circus in the lower leagues like Diego Maradona Jr, rely on nepotism and Instagram to play for their father’s MLS franchise, or simply and wisely decide to go into something else. Genetically, they have won the lottery, but the personal drive required to make it often gets lost in the privileged lifestyle that their father’s talent has afforded them.

Make no mistake, Cesare Maldini was a giant of Italian football, a world-class player with bags of talent. In 1963, he achieved iconic status when he strolled up the Wembley steps to become the first captain of an Italian club to lift the European Cup, Milan coming from behind to beat Benfica 2–1, five years after Real Madrid’s Paco Gento had scored deep into extra-time to seal a 3–2 victory and break Rossoneri hearts. Cesare oozed class as a footballer. An artisanal stopper who became an artistic libero and could pass off both feet like a number 10. One who, despite his slavish devotion to the tactical approach of manager Nereo Rocco, couldn’t help but on occasion grease the lock and slip the catenaccio, galloping upfield to join in the fun. Four scudetti. Team of the Tournament at the 1962 World Cup. One European Cup. World Class. A giant.

Based on empirical evidence, our own experience and those of people close to us, we know that father and son relationships can be challenging. And in case we ever manage to forget our own shortcomings, there is always culture. From the ancient allegorical stories of Odysseus and Telemachus and Daedalus and Icarus to more modern in your face illustrations like Homer and Bart Simpson or Tony and AJ Soprano, we are reminded that that being a son can at times be like walking through a minefield blind, and being a father is a high-wire act that requires balance, intelligence, and constant imperceptible readjustments to ensure the worst doesn’t happen.

Cesare Maldini was a giant of Italian football, but more than that, he was an incredible father. Tiptoeing along the tightrope above and providing just enough shade for Paolo to move through life’s obstacles without ever allowing the shadow of his achievements to make success impossible. When Paolo was born in June 1968, Cesare had been retired a year. His mantelpiece should have been heavy with trinkets, his hallway bearing at least one image of him lifting a trophy. Nothing.

“I always dreamed about being as good as my dad, although I knew very little about him as a player,” Paolo told Gazzetta dello Sport in 1998. “I only learned through looking at three albums of press cuttings that had been collected by a friend. They were the only records we had in the house. I knew that he was a great player, but he never explained to me how he played. When I was a boy, I used to look at those albums a lot.”

Like all good fathers, Cesare encouraged his son to do things he loved, and Paolo loved football. He played as a goalkeeper at school for a while, but when he began showing athletic and technical promise aged 10, Cesare offered to take him for a trial. Aware of the problems his name could cause around the dusty pitches of Milanello, he gave Paolo the choice between Inter and Milan. There was no pause. He wanted to be Rossoneri, like his dad. It’s what he had always wanted.“From the moment I first remember seeing a picture of him holding the European Cup, I wanted to copy his success,” Paolo told World Soccer magazine years later. “I think he was harder with me than with the other players in the youth teams at Milan. But I know that was only because he wanted to make sure no one could accuse him of showing any favouritism. In the long run, that made me try harder to succeed. I wanted to do it for myself, but I owed it to him.”

By the time Paolo entered Milanello, skinny, tousle-haired, a walking, tackling, cajoling mini Cesare, his old man had won a Cup Winners Cup and a Coppa Italia as the Milan manager and had recently taken up the role of one of Enzo Bearzot’s Italy assistants. Imagine how easy it would’ve been for him to get it wrong, what with his CV and who he was. But rather than force too hard or hold back too much, he nailed it. He’d drive Paolo to training and study him nervously, chain-smoking as his boy made the same tentative steps he had decades earlier. He’d talk to him about where to be and the work required and the goals you needed to set to make it, and he watched with pride when Paolo was gradually sucked backwards from the right wing to a place in defence from where he could ooze his class, show his tactical discipline, and occasionally gallop off up the flank to join the fun.

Cesare Maldini had no training in being a father, who does? He was the son of a fisherman, raised mainly by his mother while his dad was away doing what fishermen do. He made it as a young player at Triestina who Milan snapped up after 32 appearances in the same way he made it as a father—hard work, talent, humility, and a bit of luck.

Paolo Maldini didn’t make it as a footballer just because he won the genetic lottery, but because he got the bonus ball on the emotional one. He wouldn’t go onto double his father’s career appearances because of his family name, nor win all those scudetti and European Cups because his dad was a world-class footballer. He did it because Cesare nurtured him and gave him the tools to do it. He became a player known for fairness, longevity, and resilience because his old man helped him navigate the minefield.


Back in Udine, midway through the second half, Franco Baresi is caught out of position, and the Zebrette try a quick ball through the middle. The crowd moves as one. For a second, they forget the cold as their hearts pump faster; the sound that only a football crowd can make when something good might happen hangs in the air. Without any fuss, on a pitch that cattle would simply refuse to have anything to do with, the tall, slender kid with the piercing blue eyes makes a recovery run from the flank, slides in from the side and takes the ball cleanly, keeping it under his control as the forward sprawls in the mud. The crowd sits back down. Spidery veins in their faces throbbing, clouds of angry breath and exasperated cigar smoke joining together to float down towards the bench.

There, sits manager Nils Liedholm. A giant of Italian football, a former teammate of Cesare’s, and the captain of the Milan team that lost to Real Madrid 3–2 in the 1958 European Cup Final. He bangs together his gloved hands, half to keep the cold from his bones, half to clap the boy he has given his debut. More than a curiosity now. Different versions of the same answer floating into the ether, louder as the confirmation passes around the stadium.

“It is him. That is Cesare Maldini’s boy.”

Part 02—L'Immortale (The Immortal)There is a familiarity to the surroundings in Camp Nou on May 24 1989. Tens of thousands of red and black scarves swirl over the heads of the temporary Milanese diaspora as the teams walk out onto the grass. Horizontally all around the vast bowl and up and down the steep climb from pitch level to the gods, the orange glow of freshly lit flares illuminate the faces of the travelling horde. Behind one goal hangs the BRIGATE ROSSONERE flag, folded up in San Siro and transported here, the central foreboding skull and stench of pyro and the rolling fans giving this grand old venue the appearance of a pirate ship.It is loud. Really loud. 97,000 of them jammed in from port to starboard to see Arrigo Sacchi’s Milan take on Steaua Bucharest in the final of the European Cup. The Romanian team are dangerous, winners three years previous and confident they can hurt anyone with future hall-of-famers Marius Lăcătuș and Gheorghe Hagi in the ranks.

Down at pitch level, things are increasingly familiar for Paolo Maldini. On the back of the white change strip, the number three. His shirt since the first game of the 85/86 season, a period in which so much has happened that blinking is not really an option, but closing his eyes is sometimes the only way to reflect. 21 years old now. Over 150 appearances to his name since that first in Udine; a scudetto winner and Italy regular who has gone toe-to-toe with Diego Maradona and Michel Platini and a whole host of international and domestic bruisers. A multifaceted player. One who shows an over my dead body approach to defending combined with a balls-out devil-may-care attitude in attack. He’s widely regarded as the best left-back in the world.

Ahead of him, Carlo Ancelotti walks around slowly and finishes a few light stretches like he’s popped out to have a crafty morning fag under the guise of taking the dog for a piss. He’s not a Rossoneri by birth, but has been the midfield conductor of Arrigo Sacchi’s game-changing rock opera since arriving from Roma. Further up, spread around the centre circle, lurk the Dutch trio who placed gold, silver and bronze in the most recent Ballon d’Or. You know them, but that hasn’t stopped your pulse quickening. These are legends we are talking about. The striker Marco van Basten strolls around, long-limbed, elegant, the languid air of a man with 31 goals to his name already that season. Ruud Gullit does a series of high box jumps, summoning the explosiveness that, combined with his technical superiority, makes him the complete footballer in any position he chooses. Frank Rijkaard looks forward, anchor {i}and{i} tiller of the good ship Diavolo.

To Paolo’s right, already in position, are two fellow sons of Milan. Closest is Franco Baresi. 29. The icons’ icon. A sweeper of such class that people still whisper about him today. He was there when Paolo made his debut, and was alongside him the previousd summer when both made the Euro ‘88 Team of the Tournament. Next is ‘Billy’ Costacurta, two years older than Paolo but only 30 games into his Milan career. Tall, correct, effortlessly functional. And on the far right, the Roman Mauro Tassotti. The indefatigable physical presence, the cudgel to Paolo’s cutlass, the one he watched from the academy and decided he'd better work on his left foot because he wasn’t getting in at right-back anytime soon. Future generations would know them as the best defence in history, the bedrock upon which the Immortals were built. But at that moment, for 90 minutes at least, they had their feet planted in the mortal realm as the Camp Nou sizzled with expectation.


So how do you become immortal? How does a team become forever known as Gli Immortale in the hearts of Rossonere everywhere? Black and white pictures cut from a newspaper and stuck to spluttering fridges and children named Paolo and Franco getting their cheeks squeezed and hair ruffled and reminded who they are named after on every birthday and twice at Christmas. A team to reminisce about when the cork comes out of the bottle, one to argue about when someone swaps Barolo for Grappa.

Of course you do it by winning football matches. You win back-to-back European Cups and do it in such a way that people can never forget you. But what about before that? The graft that underpins the craft? Paolo Maldini didn’t become the world’s leading left-back simply because he was good, and he wasn’t part of the diamond standard defence by luck. And the way in which he got to this first major junction of his career tells you a lot about who Paolo Maldini is and why he will go on to play at the highest level until he’s 40In 1986, a former cruise ship singer turned Napoleonic media magnate and future bunga bunga practitioner bought AC Milan. Silvio Berlusconi was hellbent on change at all cost, and to his credit, appointed his first manager on a hunch after being impressed by the drumming his Parma team meted out to the Rossoneri. The press went for Arrigo Sacchi and his apparent lack of credentials, christening him Mr Nobody. Sacchi didn’t care, the one-time shoe salesman was singular in his vision and backed himself to the hilt, but to shut the press up and succeed in his mission of revolutionising Italian football from a tactical, cultural and athletic perspective while overseeing Milan’s transformation into the best team in the world, he needed people to follow him.

Paolo Maldini followed him. Even at 19, he was the ultimate professional. Schooled in the need for sacrifice by his dad, he’d spent hundreds of hours working on his left foot until it was as good as his right to increase his options for breaking into the team and staying there. But what Sacchi demanded was different; he was changing their minds and habits ingrained over years; he was attempting to subvert the very psyche of Calcio, asking them to go from passive, static, and reactionary to a marauding team unit that moved like a plague of locusts, endlessly proactive with and without the ball.

“He was almost maniacal in his search for perfection,” Paolo said of the early days under Sacchi. “It was intense. I used to get home at night feeling exhausted. Everything was really difficult.”

One of Sacchi’s favourite drills in the early days was the 10 v 5. He’d get the back four and keeper—who he called ‘my five’—and line them up against ten attackers who could go anywhere. He’d sometimes start it without the ball, attackers moving and switching the positions and the defence moving on each other’s body language, the idea that they became hyper aware and able to do it all without speaking. Connected by an invisible string. Then he would run it with the ball. Full pitch, the attackers charged with simply having to score, and if the defence won the ball, the attackers had to retreat ten yards further back and start again. The attackers never scored. Not once. He ran that drill again and again and again, and Ruud Gullit and Marco van Basten and the eight others did not score one single goal. Ever.

Paolo Maldini was, in many ways, the ultimate beneficiary of Sacchi’s revolution. It’s not as if he had never attacked before Sacchi, but, post-Damascene conversion, his athleticism was used as a weapon in both phases. A full-on blitzkrieg up and down the flank, his success in games the reward for punishing himself physically, mentally and emotionally in training until he was spent. Not that he will take any credit.

“If we got to a very high level, leaving an important legacy, the merit is his,” he has since said of his former coach. “And If I became a perfectionist, it is also thanks to him.”


As the full-time whistle blew in Barcelona, the football world took a collective gulp. It had seen Milan destroy Real Madrid 5–0 in the semifinals, but this was a final, and Steaua hadn’t lost a domestic game in three years. It was a bloodletting. A ransacking. 90 minutes of sustained orchestrated brilliance. Two goals each for Marco and Ruud, 10/10 performances everywhere on the pitch. Paolo up and down, winning his headers, tackling with ferocity, following Franco up and across the pitch to shrink the space, showing why he was the best left-back in the world.

The next morning, L’Equipe announced that “Watching this Milan side, football can never be the same again.” Mission accomplished.

Part 03—L'Invincibile (The Invincible)Paolo Maldini takes a deep breath. Everywhere he looks, his teammates lay prone or wander aimlessly, staring the full thousand yards out past the contours of the Rose Bowl and into the Californian sky. He bends at the waist and leans forward. His hair, jet black and drenched from 120 minutes of punishment in the brutal Pasadena sun, falls to cover his face. Sweaty hands find tired thighs, aching quadriceps that have pumped endlessly for a month, pushing him through seven games and hundreds of tackles. Around his neck, a silver medal hangs down and catches the light. It’s scant reward for shutting out Brazil in a World Cup final, for showing the hundreds of millions watching that he is the best centre-back on the planet.

He’d only been playing the position for two months.


The phrase ‘necessity is the mother of invention’ has its roots in Ancient Greece. In 375BC, Plato wrote that ‘our need will be the real creator,’ and over time, it evolved to the more direct and anglicised version. So, in that sense, it’s fitting that Paolo Maldini’s conversion to centre-half came in Athens 61 days before events in Pasadena, and was based on need rather than any tactically inventive tinkering. Franco Baresi and Billy Costacurta were both unavailable for a Champions League final against Johan Cruyff’s feared Dream Team, and Milan were supposedly there to make up the numbers such was the perceived superiority of Barcelona.

You know the rest. 4–0 Milan, a ruthless display from an angry team. Cruyff made to eat his prematch words. Maldini the lynchpin, neatly folding up Stoichkov and Romário and popping them next to his comb in the back pocket of his stonewashed Armanis.

Of course, he was not a complete stranger to the position. For a start he was genetically predisposed to the role’s physical, technical, and mental requirements. And for as long as he could remember, he’d had a permanent front-row seat from where he could watch Franco go to work, an experience that in the years before and since Fabio Capello replaced Arrigo Sacchi was the footballing equivalent of apprenticing at Da Vinci’s knee. Between May 1991 and March 1993, with Sacchi having departed to manage Italy, Milan had gone 58 Serie A games unbeaten and had wrapped up a third consecutive league title weeks before the Champions League final. The immortals had become the invincibles.

Paolo played pretty much every one of those 58 games at his favoured left-back. He was now a real physical specimen, filled out but lithe and rangy, like a nightmare super-middleweight, too big, too quick, and too powerful for opponents. Tommy ‘Hitman’ Hearns in Nike Tiempo. His rampaging in attack and ability to neuter any opposing winger reasons why his redeployment was seen as a temporary measure.


It’s June 23 1994, 49 minutes into Italy’s second group game in Giant Stadium, New Jersey, and the wheels are falling off. Tongues are already wagging back home. A nationwide inquest after the opening loss to a Paul McGrath inspired Ireland. As Franco Baresi leaves the field with what turns out to be a cracked meniscus, Paolo Maldini takes the captain’s armband, rolls it up his left arm, and straps himself in.

It’s a sliding doors moment. The beginning of a baton change between teacher and student that will stretch over the next few seasons, and one that for the next five games leads to a polymathic display of defensive artistry.Anybody who watched this World Cup, let’s say on a 12-inch TV in their bedroom after flunking their GCSEs, or saw a lot of Maldini up close will undoubtedly find it reductive that his career has in many ways been boiled down to a 58-second social media supercut of his slide tackles. It’s like only showing Tommy Hearns’ knockout reel or deciding everything you need to know about Da Vinci based on the Mona Lisa. The tackles in isolation are wonderful, but they lack context and are mostly reactive. A shame. really, because Paolo was a terrifyingly proactive defender.

From the opening whistle of the third group game against Mexico,, to the final whistle of the semifinal against Bulgaria, which Roberto Baggio wins with two early goals, he never left the front foot.

Over 120 minutes against Nigeria, he dealt with and overcame the wizardry of Jay-Jay Okocha, the direct threat of Daniel Amokachi and the predatory instincts of Rashidi Yekini (known brilliantly back home as The Goalsfather). The quarterfinal against Spain was a gruelling Latin chess match in a dusty square in the midday sun, a triumph of the mind as the vultures sat on the rooftops waiting to pick on the bones. In the semifinal, a reunion with his old dancing partner Hristo Stoichkov. A player who could run you, batter you, and skin you. Pistols at dawn for the pair who could have strolled off the pitch and into a spaghetti western.

The aggression in every part of his game is remarkable to watch again 28 years on. Springing out of the traps to intercept, he makes himself felt every time. His ability to recover once, twice and three times in succession proving how highly he cherished defending.

He’s a walking coaching manual. Touch tight to the point of exhaustion, covering the channels and sending the fullback inside to goal while he blocks the crosses. Stepping out of tight situations and following a tackle with a backheel. Imperious in the air. Unbeatable on the floor. Consummate and courageous, educated and electrifying. Dropping naturally behind Costacurta like Franco had done to sweep, but being right where he needs to be if it's time for the offside trap or to get the line high. The communication. The intelligence to decide when it is time to step out and play or when hitting the strikers early with 40 and 50-yard pinpoint passes off both feet is a better option.

All over the world, hundreds of millions watching are sold. A 12-inch screen in the Midlands my portal to a different type of football. A different type of player. The idea of what central defending should be crystallised forever by a man who looks like he has played there all his life but infectiously treats every game as if it is his last. A rhapsody in blue. An apprentice turned master. A renaissance man in fold-over tongues.


Paolo Maldini takes a deep breath. All around him, his teammates are moving with purpose, intently focussed on the job ahead. The 94,414 in attendance and the searing heat an afterthought as he stands tall. An all-timer of an Italy shirt clings to him, 5 in the middle of his chest, a world-class typeface that is repeated on his right thigh. White shorts, blue socks, the full Azzurri. If he looks over to the Brazil dugout, he’ll see a buck-toothed phenomenon wearing braces who, in time, will inhabit the same city as him and against whom he will judge himself. One day, Ronaldo will tell the world that Paolo is the best defender he faced. One day.

Paolo is only looking forward. Blinkers on. He’s 26, has won everything at club level, and by the year’s end, will finish behind Stoichkov and Baggio in the Ballon d’Or. His hair is molasses black, longer than it used to be, and it frames a jaw that appears to be carved from marble. He can see Romário and Bebeto, smiling assassins who will pull your pants down before cutting your throat, and he knows he is going to have to go to the well. On the front foot, proactive, radar on, all of the things he learnt sat on his father's knee and the others he has studied standing by Franco’s side. The innate, the empirical, and the instinctive combining to make him invincible.

Part 04—Il Cuore di Drago (The Dragonheart)Federico Giunti is 30 yards from goal. He’s your archetypal jobbing 90s Serie A defensive midfielder, a career written for Championship Manager. He waits to take the free kick as AC Parma get organised. It’s a real who’s who in the box. George Weah and Oliver Bierhoff are bobbing around looking for gaps, walking five yards this way and three yards back, attempting to move the defenders or, at the very least, make them uneasy. The old cat and mouse.

Gianluigi Buffon screams; that’s what he does. Lilian Thuram, Fabio Cannavaro, and Nestor Sensini are talking to each other, trying to be heard over the keeper. They're always trying to be heard over the keeper. The back four of the greatest cult team of them all; blue and yellow hooped Lotto kit, Parmalat sponsor, the black cross over the heart. Somewhere, Hernan Crespo is lurking, waiting for the counterattack. He’s having a belting season that will end with a Coppa Italia and UEFA Cup double, and he’ll score in both finals. But today, April 11 1999, I Crociati are 1–0 up in San Siro after 58 minutes; win, and they leapfrog Alberto Zaccheroni’s experimental Milan into third position in the league.

The whistle blows. Paolo Maldini shouts at Federico Giunti for the ball. He’s been standing five yards ahead and just off to the left, Juan Sebastián Verón half keeping an eye on him with his hands on his hips. The pass from Giunti is rolled, diagonally, to exactly where Paolo wants it. Verón is not bothered. And in his defence, why should he be bothered? Maldini hasn’t scored in the league for two years, and he’s never been prolific. But he’s angry. Fuming. Eighteen months of misery boiling up inside. The sting of failure and the inquests that come with it rolling around in his head. The captain’s armband. Heavy. Like lead. White hot and taken straight from the forge and wrapped around his bicep.

That is the Paolo Maldini who moves onto the pass.


It was Carlo Pellegatti, the excitable Milan commentator who first called Paolo Maldini Il Cuore di Drago. Dragon Heart. One thing that often gets lost in the career narrative of Maldini is how brave he was. Not just brave, but hard. He might have looked like he had walked straight off a runway at Milan fashion week, but he spent a quarter of a century thundering into tackles, repeatedly breaking his nose on the elbows and heads of strikers, and scrapping with all sorts of bastards. He could be dirty, sly, and intimidating when needed.

And if there was ever a time in his career when Paolo Maldini needed his heart, it was his first season as full-time AC Milan captain. Franco Baresi and Mauro Tassotti had retired at the end of the previous season, which in itself had been one to forget. Fabio Capello was back at the helm after his year-long sojourn in Madrid, looking to restore the normal order of things with the signings of the free-scoring Patrick Kluivert, the flying Ibrahim Ba, the commanding Brazilian André Cruz and the inventive Leonardo.

It was a disaster. 1997/98 was Milan’s worst season in nearly two decades. Capello a down-at-heel circus owner traversing Italy, rolling into different towns with his collection of fading stars and seemingly incapable of inspiring their replacements. A collection of sad lions, drunken unicycle riders and trapeze artists who couldn’t catch each other in a phone box, the paint peeling off the wagons as they were laughed at from north to south.

A 1–0 loss at home to Vicenza started the rot, and things just got worse. Pumped 3–0 by Inter with Ronaldo feasting in plain sight. A brace each for Del Piero and Trezeguet in Turin the following week. On it went, and the worse it got. Their former ringmaster Roberto Baggio twirling his baton and cracking the whip in Bologna and scoring twice. A 5–0 shellacking in Rome, the pointing fingers and laughing faces haunting the journey home. The final day loss in Florence. Paolo at right-back, left-back and centre-half. Moving all season to plug gaps as the goals against column kept getting fatter. Whispers about his age, about the captaincy. 10th place. Capello sacked.


There is a remarkable amount of space ahead of Milan’s number 3 as he moves onto Federico Giunti’s pass. Verón is watching, ambling. Buffon is on his line, and the rest of his back four are still playing cat and mouse with Olivier and George. Paolo takes one touch out of his feet and towards goal. Maybe Verón thinks he is naturally left-footed, or maybe he’s just concentrating on being in position if the ball drops so he can spring Crespo with one of the outrageous passes he’s become known for.

Buffon runs off his line and screams; he knows that Paolo is not naturally left-footed and that he is not on his swinger here. He’ll have seen the highlights of the occasional bangers sat at home as a kid, and he’ll have nodded his head on international duty when Paolo has joined in the finishing session at the end of training. But he’s moved too late, and his defenders haven’t reacted quickly enough. The strike from 21 yards is pure, really clean, one of those you hit so well that you don’t feel it off your foot. He is staring at where he wants it to go as his head comes up, the ball screaming off his right boot past Buffon’s spreadeagled dive. It hits the inside of the post hard and ricochets into the net. Nestor Sensini looks like he might combust as Verón throws his arms up in the air and Lilian and Fabio lead the inquest as the crowd begin to dance.

Paolo explodes as the past year and a half is exorcised, his captaincy finally meaning something, the weight and heat of the armband receding as his teammates leap on him. They know this is big. Seasons turn on moments like this. 13 minutes later, Maurizio Ganz scores the winner for Milan. San Siro turned into the big top for the first time in an age.

After not being top of the league at any time since September, Milan put on a real show following the Parma game. The wagons are covered in fresh paint, the unicycle riders are off the turps and the lions are hungry, ready to snap at those who laughed the year before. They beat Udinese 5–1, going top as Lazio falter. Edge a thriller against Sampdoria in Genoa, and turn Juventus over in Turin. Six games, six victories, their captain ever-present as they only concede four times and win an unlikely scudetto on the final day in Perugia. Paolo running topless across the pitch and waving the shirt. Il Cuore di Drago beating in his chest.

Part 05—Il Capitano (The Captain)As South Korea’s right-back, Lee Young-pyo, cuts back onto his right foot, Paolo Maldini does not know he has entered the last five seconds of his international career. 126 caps. Ten thousand eight hundred and eighty-four minutes. Captain for eight years. He’s played every second of this tournament so far after spending two months out with a ruptured knee tendon. When he went down against Atalanta back in December, the first thing he thought of was The Azzurri. The 2002 World Cup. 34 years old. One more chance.

What he does know is that, with 117 minutes gone, he is in trouble. The trajectory of the ball and his body position are going to cause problems. Caught under it, they call it. He’s closed off, half turned, backpedalling and without a solid base to jump from. He is knackered. Even without the refereeing, it has been a gruelling game in Daejeon. End to end. Penalties refused and a penalty saved. A red card for Totti. The co-hosts relentless in front of a partisan crowd, their bravura attacking style grooved for months by Guus Hiddink in the lead up to the tournament.

Paolo watches the ball, sees the runner, and tries to jump.

Ahn Jung-Hwang has got the drop on him. A diagonal run providing the velocity and up he springs. His long hair exploding as he glances the ball down into the floor and past Buffon, landing and sprinting off, screaming wildly to lead the type of celebrations that only a golden goal in a knockout game can bring.

The host broadcaster jumps from camera to camera. Giovanni Trapattoni calls the world a figlio di puttana, Gennaro Gattuso is on the floor, and then there is Paolo. Hands on hips, a huge exhalation, eyes closed. The montage will be playing soon, if it's not already. This final ignominy stitched onto the end by his own brain, the strings of a particularly mournful composition wrapped around 14 years of international heartbreak.


We're not really ones for nihilism; for a start, it sounds exhausting, and who is going to wear all those nice vintage away kits if we’re head to toe in black all the time? But, and you’ll have to excuse the pop-psychology for about 30 seconds, there is one thing Nietzsche said that rings true when examining the yin and yang of Paolo Maldini’s career. He reckoned that extreme hardship and extreme joy sort of go hand in hand; that you can’t really experience the highs of one without the lows of the other.

“Examine the lives of the best and most fruitful people and peoples and ask yourselves whether a tree that is supposed to grow to a proud height can dispense with bad weather and storms… What if pleasure and displeasure were so tied together that whoever wanted to have as much as possible of one must also have as much as possible of the other—that whoever wanted to learn to “jubilate up to the heavens” would also have to be prepared for “depression unto death”?

Paolo Maldini never got to jubilate up to any heavens in his international career. It was, in his own words, a career of failure. Not just losing, but losing in the cruellest ways over and over.

Italia 90 was the big breakout tournament alongside Baggio. A pair of freewheeling tyros flourishing in Totò Schillaci’s shade, bursting out of those deep blue shirts in front of a home crowd, careers stretched out in front. Real halcyon days stuff. A Bruce Springsteen song. And then, bang. Losing a semifinal on penalties in Naples to Diego Maradona and Argentina and everything becoming gobbled up by that narrative.World Cup 1994. We’ve been there. Holding the defence together with sticky tape and sweat for five games, and then what? Penalties. Again. Euro 96? Your first as captain? A farce. Arrigo Sacchi has gone full metal jacket, he’s still not recovered from the fallout in the US, and you limp home without making it out of the group.

France 1998. This could be the one. You’re not favourites, but you have an exceptional squad and a manager you love. Your dad. Papa. Cesare Augusto Maldini finally getting his chance after years of coaching age group teams to international success. He goes with what he knows. Three man-marking defenders and a sweeper, Nereo Rocco’s catenaccio with a big man and a little man up top. You don’t lose a game in the group, but back home, the press are hammering your dad. An icon of Italian football, they paint him as a relic to be torn down. You beat Norway 1–0 and move onto the quarterfinals against France. It’s a running joke now. Extra time. Penalties. Papa falls on his sword.Euro 2000. The final. Two years before events in Korea. Twenty-four months is a long time, but the misery is so fresh you can still taste it. France again. Zidane and Henry and Deschamps again. You take them deep. A hundred and three minutes on the clock when a ball is cut back from the byline. David Trezeguet has pulled into space, and you are rooted by the penalty spot, frozen. Before you get to move, bang. A left-footed volley for the ages. A golden goal.

“Examine the lives of the best and most fruitful people and peoples and ask yourselves whether a tree that is supposed to grow to a proud height can dispense with bad weather and storms…"

It’s a bit dramatic, but once you have looked at Paolo Maldini’s career through this prism, it’s impossible to think of it any other way. It’s not a conscious thing, but it is very real. Otherwise, how do you explain the flip side? That pretty much every time he suffered a cruel failure with Italy, he was experiencing extreme joy with Milan. Two European Cups before Italia 90, three straight league titles and a European Cup after it and before 94. The surprise scudetto after the misery of France 98. Man of the Match in a Champions League final in 2003, 10 months after Korea, winning on penalties and lifting the trophy as captain 40 years to the day since Cesare Augusto did the same at Wembley.

What if pleasure and displeasure were so tied together that whoever wanted to have as much as possible of one must also have as much as possible of the other…

Onto 2005, scoring the fastest goal in a Champions League final and losing on penalties after seeing a 3–0 lead slip away. The worst day of your career in Istanbul. 2006, turning down Marcello Lippi’s call to come out of retirement and watching on as the Azzurri, the team you captained 74 times, the team you bled for and cried for, win the World Cup on penalties. Imagine that.

“Whoever wanted to learn to “jubilate up to the heavens” would also have to be prepared for “depression unto death”?"

The double hardship forcing you to keep going. Body hurting as you enter your 11th season wearing the armband. Il Capitano. An invincible. An immortal. Dragon heart giving you the energy to keep on pushing the season after Italy lifts the Jules Rimet. Delaying surgery, ignoring your wife and the doctors. It’s always been about winning, from looking at the scrapbooks of your dad to pretending to be him in the youth team to following Arrigo and listening to Franco. You have always wanted to win. It’s how you cope with losing. Pleasure and displeasure. Pressing play on the happy montage. Red and black and ticker tape, stadiums rolling like pirate ships to a soundtrack of booming operatic stanzas.

2007. Athens. Another Champions League final. Full of painkillers and analgesics, you don’t remember much of the 2–1 win. Someone will tell you afterwards that Liverpool were the better team; hardship and joy. You wait, trophy in front of you. And at that moment, you don’t recall the depression unto death of Naples, and Pasadena, and Rotterdam, and Daejeon. You lift the trophy towards the heavens. Jubilation. Il Capitano.

Part 06—Il Papa, Il Figlio, Il Leggenda (The Father, The Son, The Legend)It’s unseasonably mild in Stadio Artemio Franchi. Normally by this time of year, Florence would be roasting. Brits and Americans littering the bridges and the Piazzale Michelangelo, sitting in the tourist trap restaurants and getting skinned for a margarita and moaning about the heat. The weather, though, is not important. Neither is the result; not even the Viola fans seem bothered. Fiorentina 0–2 Milan. Alexandre Pato and Kaka with the goals. Beckham, Seedorf and Inzaghi all in the starting line-up. Ronaldinho on the bench. Carlo Ancelotti in the dugout.

In the Milan end, a homemade banner is proudly unveiled. There is no art to it. Letters hastily drawn on a bed sheet, coloured in red and black. But it’s all love, both in sentiment and design.


The whistle blows, the stadium DJ fires up “Life is Life” by Opus, and Paolo begins to clap. His teammates and his opponents walk in to hug him as the Fiorentina fans unfurl a banner of their own. It’s been a long goodbye, but one that he has played a full part in. He’s started 32 games in all competitions and played 90 minutes in most of them, but this is it. Finito. A quarter of a century, over 1000 games, all those trophies and heartbreaks, the tackles and headers, the rousing half-time speeches and the impeccable timing, it’s all done. The 16-year-old who anonymously walked on at half-time in Udine finishes as a 40-year-old to global adulation.

He starts to jog and wave toward the crowd. His wife is there, and his sons, Christian and Daniel. Adriana beaming and waving; the boys are just kids, unaware that a nation is watching them. The camera switches and focuses on a tall, imposing figure. Now 77, but still immaculately turned out, aware that everyone is looking at him. Cesare Augusto and his big, heavy claps, his face a mask of pride that nearly breaks. He composes himself, swallows the quiver, and salutes him all the way into the tunnel. His boy. Paolo Cesare Maldini.

April 5, 2016. Milan.

On April 3 2016, AC Milan posted a picture of a man in their famous white away strip. Badge on his heart, captain’s armband on his left bicep. He’s holding the European Cup above his head and screaming with joy.

“Goodbye dear Cesare,” started the message.

“Today the world loses a great man and we lose a page of our history. You will be missed.”

Two days later, following his funeral at the Sant'Ambrogio church, Paolo and his five siblings shared an open letter.

"We just want to thank you for the wonderful and unique journey we had together. It will make us smile every time we think of you. We were close in every moment, not knowing that you were going.

"When you left us an extraordinary thing happened: we were inundated with messages of affection for you, not banal sentiments, touching ones.

"You left a little bit of yourself in all these people.
"Thank you, Papa."

September 25 2021, Spezia.

We are 48 minutes into a tense stalemate in front of 6000 fans in Liguria. Rafael Leão moves away from the Spezia right back and gets hold of the ball. He’s on the left flank, 45 yards from goal. He turns inside, puts his foot to the pedal, and he’s off. Eyes up, ball under control, he spies the Milan right-back Pierre Kalulu in space and drills the pass over to him. It’s a perfect crossing position. Kalulu receives the ball with his body open, and with his first touch, pushes it into the channel. One look up, and he delivers the cross. It’s a bad area for the keeper, outswinging and begging for a runner.

Milan’s number 27 obliges. He’s ghosted in diagonally from beyond the back post. It’s his first start in Serie A. Tall, skinny, familiar. The run is perfectly timed; up he goes between the centre-halves, a bullet header sealing his first senior goal for the club. Daniel Maldini celebrates with his arms outstretched, like an aeroplane.

Up in the crowd, the focus turns to a tall man. Now 53, immaculately turned out, Paolo is going nuts. Shouting and smiling and telling everyone around him that his boy has scored. He might be there in an official capacity, but for those few seconds, he is il Papa. The circle is complete.

May 23 2022, Sassuolo.

When Paolo Maldini retired as a player, he knew he would never be a coach. He’d decided a long time before, clarifying it to the world when he turned down an offer from Carlo Ancelotti to join him at Chelsea not long after he finished playing. Maybe it was because he saw what his dad had gone through, maybe he just didn’t want to coach and, for a while, he was just retired. Sure, he had a brief dalliance with tennis and played one game as a professional, but for a long time, he was just an ex-footballer living in a beautiful white stucco mansion just outside Milan and occasionally giving interviews.

Then, in June 2019, a decade after jogging off in Florence, he was made Technical Director after a year as an assistant to Leonardo. He has unsurprisingly taken to a wide-ranging role with aplomb and is a canny appointment by the club’s owners. His status means he’s more than just a member of staff. He’s a selling tool for new signings—Theo Hernández said he was the main reason he signed—and a reference point for current players. He’s a living, breathing icon who sets the standards required for the club just by being there. Imagine sitting down to negotiate a transfer with L’Invincibile. Imagine talking about back to back European Cup wins with L’Immortale over an espresso at Milanello. Imagine thinking you had disappointed Il Cuore di Drago.

His dad once said that Paolo was a “true Rossoneri, his soul belongs to Milan”, and you only have to observe him watching games to understand how seriously he takes this. How it hurt him watching the club’s lack of success in his time away and how he shuns any limelight to focus on the job at hand, dragging Milan back to the top of the pile.

So forget Zlatan smoking a cigar and turning over a table, the defining image of Milan’s first scudetto in 11 years was of Paolo Maldini, huge grin on his face, high-fiving his son after a 3–0 victory on the road confirmed the Rossoneri as champions. It was a high-five that stretched back to 1954, when a promising young libero joined and went on to win four scudetti, one that reminds you it’s impossible to spell Milan without Maldini. The dynasty continues.


The Chronicles of Paolo Maldini was originally published as our Issue 22 cover story. That magazine is long sold out, but you can subscribe so that you never miss out again by clicking here.

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