Illustration: Sammy Moody

Antonio Cassano spent his first seventeen years with nothing, then got everything all at once. On a Sunday afternoon in December 1999, the Bari teenager scored a dream goal against Inter, and went back to his house to find people outside offering him food, lighting fireworks and firing gunshots into the air. “The whole city was there for me,” he wrote. The press billed him as the successor to Roberto Baggio and a future winner of the Ballon d’Or. Having grown up in one of the poorest slums in Italy, with no money, no girls and little to eat, Cassano soon had plenty of all three. Nine years later, he’d claim to have slept with six- to seven hundred women. Yet his career would dwindle to the extent that he’d become one of Calcio’s greatest wasted talents. “He says he’s slept with seven hundred women in his time, but he doesn’t get picked for Italy any more,” Andrea Pirlo wrote in 2015. “Deep down, can he really be happy?”

At least initially, Cassano was. The goal diverted him from a likely path to criminality. A native of Bari Vecchia, he had grown up to the sound of police sirens and gunfire, making friends who joined gangs or sold drugs. A boy he knew who delivered pizza was killed by a stray bullet. At an early age, Cassano’s father left the family, so Antonio and his mother hardly had money for food. While she tried to get by as a cleaner, Cassano wrecked havoc in school, repeating years six times. The only money he made was through bets with friends on whether he could smash windows with a ball from long range. If nothing changed, he knew he’d have to steal, and he was hard to catch. “The only thing I knew how to do was to run and dribble—nothing else,” he’d write in his book, Dico Tutto. 

In the afternoon, Cassano would meet his friends at the Piazza del Ferrarese, a vast square in the old town. They played football until dark, or until police interrupted, in which case they pelted the officers with tomatoes and eggs. The games could last days, the scores running into several hundreds. Though winning counted, class counted more, and Cassano loved to entertain. Such was his talent that people stopped just to watch him. When they began to bet on his matches, he demanded a slice of the pie if his team had won—and got it. Yet even after a scout had invited him to play for Bari, he remained poor and averse to work. Only when he signed his first professional contract did he feel that football had rescued him. 

Another outcome would have been a great loss not just for him, but for Calcio. Blessed with balance and technique, Cassano would dazzle with flicks, tricks and roulettes. Whatever he did seemed so natural that if looked as if these gifts had merely been bestowed on him at birth. (Perhaps they had.) Once at Bari, he rose so fast that, as he put it, he practically went from the town square and straight to the first team. Winning was now key, but class still counted. In one training session, Cassano writes, he pulled a scavetto—a chip—on veteran goalkeeper Francesco Mancini, who spent the next three minutes chasing him around the athletics track. 

Just before Christmas in 1999, Cassano made his debut for Bari at Lecce. He started the next game, against Inter. He was seventeen. At 1-1 with two minutes left, he received a long ball on the counter. Running at full speed, he flicked it onwards with the back of his heel, making it arch onto his forehead, which he then used to nudge it forward. With Christian Panucci and Laurent Blanc chasing him, he dribbled both, and scored. Bari beat Inter 2-1. 

The whole country began talking about Cassano. When he drove home to Bari Vecchia that night, his street was so full that his car had to stop. People had brought him bread, pasta, olive oil, champagne. “The day before I had had nothing to eat,” he wrote. “Now I had enough food to become obese.” As the city saluted its jewel, local gangs began to protect him: when his Porsche was stolen in 2002, it turned up at his mother’s house less than a day later—with a bouquet of flowers. Women also began to view him differently. “I was almost Brad Pitt, and all thanks to a back-heel,” he wrote. “Football really can perform miracles.”

In his 2008, Cassano noted that while everyone likes sex, some enjoy it more than others. He considered himself among the latter. Until then he had had few girlfriends and little regard for fidelity; the sudden ability to date almost anyone, he wrote, was an enormous privilege. His book describes several models with whom he has slept. In the appendix—which is includes no records or honours, but a playlist, a text on his tattoos and a recipe for panzerotti—he penned a guide to Bari Vecchia in which he explains how to charm local women. One can imagine the carefree life he lived, strolling down the narrow streets, joking and laughing, high on his own fame. “Tell her: ‘Mamma mía, what a wonderful girl you are’,” he wrote. “Smile and ask for her number. Easy, right?”

In 2001, Cassano joined Roma for €30m to become the world’s most expensive teenager. He could have chosen Juventus, but his mother found Turin too cold, and he wanted to stay close to the sea. Roma had just won their first scudetto in eighteen years. When Cassano was to meet the president, Franco Sensi, he showed up two hours late. But Sensi forgave him, and the two hit it off. The same was not true of Cassano and Fabio Capello, who stressed the value of order and discipline— two things Cassano abhorred. 

Cassano soon declared that he wanted to win the Ballon d’Or. But words were one thing, action quite another. Almost as soon as the ink on his contract had dried, he began buying cars like toys: a series of Mercedes models, a Ferrari Modena, a blue Ferrari 456 owned by Cafu. In the dressing room, Cassano placed buckets of water above half-closed doors and waited for someone to come in. When his team-mates showered, he hid their underwear. In the cafeteria, he swapped the sugar with salt. At the training camp, Trigoria, he stayed up late, stole the keys to the back door, and let in girlfriends and lovers. He hung out with Francesco Totti, his idol, who became like an older brother to him. They partied so often that Cassano would call his first two years in Rome “crazy” even by his standards. Were he to recount everything that happened, he said, he’d need three books. 

On the pitch, Cassano found it harder. The coaching staff felt he was too raw, and as Roma finished a point behind winners Juventus, he played twenty-two league games, starting only three. Yet he always expected to play, and wondered why they had paid so much for him if they didn’t start him. When Roma prepared to face Perugia in his second year, in November, he refused to show up. Come Saturday he was at home. Televisions crews had heard the rumour and turned up outside, prompting his mother to come out and deny he was at home. Cassano did not leave the house until Tuesday, when he had to train. 

Roma eventually crashed to eighth. A last shot at glory came in the Coppa Italia final against AC Milan, in which Cassano started both legs. Milan won 4-1 in Rome. At San Siro, with Roma 2-1 up, Cassano was knocked over by Martin Laursen. Enraged that no foul was given, he jabbed a finger at referee Roberto Rosetti, then raised his index- and little fingers to show Rosetti le corna—literally ‘the horns’—an insult that can imply that the person in question is being cheated on. Rosetti dismissed Cassano, who stormed off and trashed the dressing room. Roma lost 6-3 on aggregate. 

The disastrous season put pressure on Capello, but he decided to stay. By Christmas, Roma were six points clear. Cassano played more often and did well enough to get his Italy debut in November. When Cassano came back to Roma, however, Capello dropped him because he was too tired. Cassano went mad and began kicking balls into the air. As he marched to the dressing room, Capello told him to respect the team. Cassano told him to ‘fuck off’. 

Capello and Cassano seemed unable to get along. Fathered by a teacher in northern Italy, Capello embodied order and discipline. Cassano came from the more chaotic south and had no respect for anyone. On one occasion, Capello chased him around the training pitch, yelling: “Don’t run away. Only cowards run.” Though Capello was used to fighting with players, this was unusual even for him. “He had a special relationship with Cassano,” Olivier Dacourt told Gabriele Marcotti for his Capello biography. “It was one of those tough-love father-son relationships, where they are always rowing and then making up.” One day Cassano suggested half in jest to Capello that they cover their mouths when speaking, so that their silly arguments at least wouldn’t reach the press. For once, Capello did not disagree. 

At some point, however, Capello began to overlook some of Cassano’s tantrums. It seemed to work. In 2003/04 Cassano would start all but one league game and score fourteen goals in Serie A. He got booked just twice. One of those came at home to Juventus in February. Before the game he asked Capello if he could wreck the corner flag if he scored twice. Capello replied that if he struck two, he could ruin all four. After Roma had stormed into a 2-0 lead, Cassano duly scored two goals, the last being a lovely header that flew past Gianluigi Buffon. As the Stadio Olimpico exploded, Cassano threw off his shirt, ran towards the corner flag and split it in half, earning a booking and admonishment from an incredulous Pierluigi Collina. It was an unforgettable evening for Cassano, preceded by characteristic preparation. The night before, he had stolen the keys to the training ground, snuck out to have sex, and returned at six in the morning. 

In summer 2004, Italy crashed out of the Euros. Cassano went home exhausted. By now Capello had shocked Calcio by joining Juventus. As the Roma players gathered for pre-season on 22 July, Cassano asked new coach Cesare Prandelli for an extra week off. He got it. But on the 29th Cassano still didn’t fancy going, so he faked illness and showed up on 9 August. Though Prandelli turned a blind eye, Cassano was in trouble when, just three days later, Roma were to play a friendly. Prandelli put him on the left wing and told him he’d play the whole game. Badly out of shape, and in scorching heat, Cassano hardly moved. With no instructions to do so, he wandered to the right flank because it was covered in shade. When Prandelli removed him at the break, Cassano should have been relieved. But instead he raged at Prandelli for promising him the whole game only to take him off. He took off his shirt and threw it to the floor. 

In the end, the row didn’t matter. Prandelli soon resigned due to the ill health of his wife, leaving Sensi to hire Rudi Völler. In the league opener at home to Fiorentina, Cassano pushed his palm into the face of Giorgio Chiellini and got sent off. Cassano then fell out with Völler. When Völler resigned, Sensi hired Luigi Delneri. Cassano also fell out with Delneri. As spring arrived, Roma collapsed, winning one of their last thirteen league games. Sensi kicked out Delneri and hired Bruno Conti, yet Roma still finished eighth—three points above the drop zone. 

Roma now needed a saviour. In summer they appointed Luciano Spalletti. One day early in pre-season, the players were listening to music while stretching out in the gym. Spalletti turned the volume down. This annoyed Cassano, who turned the volume back up. Spalletti turned it down. Cassano turned it up. 

Spalletti turned it off. 

“Why do you turn it up?” Spalletti said. 

“We’ve always had it like this—loud,” Cassano said, and turned it back on. 

Spalletti turned it down. 

Now Cassano got angry. He turned it back up. “Listen,” he said. “You’re no longer training those useless players at Udinese. That place was your house, this is my house.”

And so Cassano fell out with Spalletti as well. Now other things also began to worry Cassano. A new deal the club had promised him never seemed to arrive. He had been made vice-captain, having played well the previous season, but Spalletti took it off him. In one pre-season game, Cassano reacted by refusing to play and going back to the hotel. By January he had featured in five league games. When the new contract did arrive, it was only half the money the club had promised. With both parties keen to sever ties, the club sold him to Real Madrid for €5m in winter. Roma immediately went on an eleven-game winning streak in Serie A, but Cassano dismissed that the problem had been him. 

In January 2006, Cassano boarded a flight to Madrid, excited to join the galácticos. He had been lucky to sign for Madrid, given his form and behaviour, but now the move could, perhaps, help him fulfil his potential. On board were a pack of Italian journalists curious to see what he’d do next. The following day came the presentation. “I got up early, at ten,” Cassano wrote. As he greeted Florentino Pérez and held up his new shirt, he wore an open brown jacket with a fur collar; a necklace, silver earrings, and a silver ring on his right little finger. Watching it back, Cassano felt he looked less like a footballer than a mafioso. “What an embarrassment,” he wrote. 

Cassano moved into a palace of a house. In training he came to admire the quiet professionalism of Zinédine Zidane, the leadership of Raúl, the work rate of David Beckham. Yet none of them seemed to inspire change in his behaviour. He befriended Ronaldo, another who didn’t like to train. Then Cassano argued with the coach, Juan Ramón López Caro, whom he later accused of lacking courage and personality. Cassano would play twelve games in La Liga that season, but started just three. Out of the favoured line-up, he turned to women and food. 

Though sources vary, Cassano seemed to have weighed about ninety kilos when he came to Madrid. The club told him to lose weight. But it was Christmas in the capital—Spain celebrates ‘The Day of the Three Kings’ on 6 January—and, as Cassano wrote, “the food was incredible”. The press began calling him El Gordito—‘The Little Fatty’. Madrid fined him for every gram he went above his match weight. But money was no issue for Cassano and, if he wouldn’t start anyway, he had little to lose. He began eating, in his own words, “like a dog”. Whether he turned up to training now depended on when he rolled out of bed. He’d throw parties at his palace, and would write that, had he had cameras there to record everything that happened, the footage alone would have made him rich. 

Cassano was in a relationship when he moved to Madrid. It soon broke down. Rich and famous, he met women in bars, clubs and elsewhere. Prior to home games, Madrid would stay at the fifth floor of the luxurious Mirasierra hotel. Cassano would book a room for a girl on the fourth or sixth floor, then invite her to his room at night. He had also befriended a waiter, whom he paid to bring up food. “Sex then food: the perfect night,” Cassano wrote. Speaking to Diario AS, he later said that he gave the waiter between two hundred and five hundred euros each time. “The only bad thing,” Cassano said, “was that he wasn’t around for the away games.”

By late February, Madrid trailed Barça by ten points. Suddenly, Pérez resigned. This was bad news for Cassano, who feared the successor would clear out the old signings. In summer, as Madrid limped to second in the league, he asked to be loaned out. “Just wait, you’ll like the new coach,” a club director told him. He was talking about Capello. 

Having left Juve after Calciopoli, Capello had ridden in on the presidential ticket of Ramón Calderón. With him came Fabio Cannavaro, Mahamadou Diarra, Emerson and Ruud van Nistelrooy. Cassano chose to embrace the appointment. Their past was well known, but wasn’t it Capello who had whipped him into shape for his fine 2003/04 season? As for their rows, with whom hadn’t Cassano argued? 

Things began well when, in the second game of the season, at Levante, Cassano scored. At half-time, however, Capello took him off. This baffled Cassano. The next four games he played, he never lasted more than an hour. The first exception came in the Copa del Rey at Éjica, where he scored and played the whole game. But on the train back, Cassano ate ten packets of crisps. Journalists on board saw it and duly wrote about it. Given his reputation, it was the last thing Cassano needed, and yet he had know the whole time that the press had been watching. “But I was hungry,” he wrote. “Was I really supposed to worry about the journalists?”

Three days later, away to Gimnàstic, Capello made Cassano and Ronaldo—another forward he struggled to keep in line—warm up for forty-five minutes without sending them on. Humiliated, Cassano lambasted Capello in the dressing room. “Have you no shame?” he shouted. “I always defended you, I always stuck up for you, and this is how you repay me? Have you no sense of decency?” Cassano also called Capello “falser than Monopoly money”. 

The club reacted by making Cassano train on his own for ten days. Coincidentally or not, Madrid soon struck up five wins in six league games to close in on Barça. But Cassano did not stay quiet for long. In an episode before a game at Espanyol, he stood near the pitch in a suit chatting to Ronaldo, Cannavaro, Diarra and goalkeeping coach Franco Tancredi. Cassano closed his suit jacket, raised his chin and puffed out his chest—it appeared a perfect imitation of Capello. That Cassano broke down in laughter afterwards added to the sense of theatre. Left alone with Diarra and Ronaldo, Cassano then moaned that Capello always chose the same players: Van Nistelrooy, Raúl. As it happened, a TV crew had filmed everything and subtitled the conversation. Cassano denied he had made fun of Capello, claiming he closed his jacket because he was cold. When the next match squad was announced, Cassano was excluded. 

At that point it seemed as if Cassano realised things couldn’t get worse. He proceeded to accuse Calderón and director general Predrag Mijatović of chasing out the Pérez players. Plagued by an ankle injury, Cassano only played four more games for Madrid. The last was at home to Gimnàstic in March, in which Capello took him off at half-time. On the last day of the league, Madrid could still win it, and Cassano was invited to the Santiago Bernabéu to watch. But he said he had stuff to do in Bari—he didn’t—and followed the game from his house in Rome. Accompanied by friends and what he claimed was fifteen women, he saw Madrid scrape to the title. As the Bernabéu celebrated, he partied into the night in Rome. He then went on holiday, forgetting his worries, not caring for anything but the present. 

Come August, Madrid sent Cassano on a year-long loan to Sampdoria. The side from Genoa had just finished tenth in Serie A. Though he knew it was a step down, Cassano missed Italy and the sea. When five thousand people came to watch him at his first training session, he felt loved. Having turned up at ninety-one kilos—the holiday had been good—he shed ten. When he struck his first goal for the club, in late September against Atalanta, he celebrated by taking off his shirt, as if to show that Antonio Cassano was no longer a fatty. That Antonio Cassano had changed. 

Then in December, he reversed the impression. Facing Fiorentina, he was denied a free-kick just before half-time, leaving Adrian Mutu to hit the equaliser. Furious, Cassano got a yellow card for dissent from referee Gabriele Gava. Cassano then began to cry, clenched his fist at Gava, and threw himself to the ground. The booking had cost him their next match, a return to Roma—which “would have been the most important game of my life”. In March, Cassano threw another tantrum when he was sent off for dissent towards the end of a 2-2 draw against Torino. As he railed at the referee, Nicola Pierpaoli, he had to be restrained. Cassano then threw his shirt towards Pierpaoli and told him he’d wait for him outside. Only as he cooled down on the sidelines did Cassano come to his senses. He’d remember thinking: “What on earth am I doing?”

Such episodes suggested that Cassano, at twenty-five, had not changed after all. The press called him Peter Pan, the boy who refused to grow up. “His is a life of bullying, crude gestures, stupidity and running away,” Germano Bovolenta wrote in Gazzetta dello Sport that season, according to The Guardian. “Then he repents, asks for pardon from all those who are close to him, who understand him. But it doesn’t last, it starts again, and he continues to lose friends and defenders—in other words, all those who speak highly of him.” 

Yet Cassano was at least playing well. That season he’d score ten goals in twenty-two league games, guiding Sampdoria to sixth. He had grown attached to the club president, Riccardo Garrone, who gave him the time and affection he required. Cassano called him “the father I wished I had.” Some have speculated that Cassano’s resentment of his own father has fuelled his problems with male authority figures—coaches, referees—and if so, the presence of Garrone could only help. That year Cassano also met water polo player Carolina Marcialis, whom he’d marry two years later. In his book, released that year, he dreamt of a life as a family man living in a big house with lots of kids. On a perfect day, he’d get up at one, get the kids from school, come home to dinner, then take her shopping. At night they’d go out to eat while a babysitter watched the kids. “The life of a king,” Cassano wrote.

The only thing that worried him was giving moral lessons to his kids. Given his past, he could imagine their responses: 

“You’re one to talk, papà, you who have shown le corna to the referee…”

“You who have thrown the shirt on the floor…”

“You who have kicked the corner flag in half…”

“You who never get up before one…”

With a beautiful city, the sea, a father figure and his future wife, Cassano was happy in Genoa. In his second year, the goals continued to flow. Under the guidance of Walter Mazzarri, he struck up a deadly partnership with Giampaolo Pazzini, leading Sampdoria to the Coppa Italia final, which they lost on penalties to Lazio. Garrone hailed them as the club’s best attacking duo since Gianluca Vialli and Roberto Mancini. The year after, now under Delneri, Cassano and Pazzini fired Sampdoria to fourth place and a place in the Champions League qualifiers. Perhaps Peter Pan had grown up after all. 

Or perhaps not. After Sampdoria had lost to Werder Bremen in the Champions League qualifiers—in extra time—Cassano refused to attend an awards ceremony. His absence triggered a row with Garrone, which grew so big that the club tried to terminate his contract in a tribunal. They had to make do with paying half his wages and keep him on, but in January he was off to Milan anyway. When he arrived, Cassano spoke as if he had realised the graveness of his latest quarrel. “I know that this is the last chance in my career,” he said. “If I fail here, I should be put in a mental hospital.”  

Milan cruised to the title that season. Managed by Massimiliano Allegri, Cassano chipped in with four league goals, two of which came against Bari and Sampdoria. Both of his former clubs got relegated. 

In October, however, with the title defence barely underway, Cassano began to feel unwell. They were sitting on the bus from Milan airport after a 3-2 win at Roma when his head started to spin. He could hardly see with his left eye. When the doctor said he’d take him to hospital, Cassano refused. They argued for half an hour. When they finally did go, Cassano struggled to speak. “I could think, but the words wouldn’t come out,” he said. It turned out he needed heart surgery. 

“I was scared,” Cassano said. “When it’s a case of life or death, everything else becomes secondary. I saw the future as grey, very grey.” What worried him most, however, wasn’t his career, but that he’d never see his newborn son again. “If there’s anyone up there,” Cassano thought, “please, let me see my son of four months one more time. Then I can go…”

Somehow, Cassano returned to the pitch after five months. Yet in summer, when Milan sold Zlatan Ibrahimović and Thiago Silva after a botched title defence, he wanted out. Not a diplomat, he joined Inter. A turbulent campaign ended with a ninth-place finish, and a row with Andrea Stramaccioni that nearly got physical. And so Cassano was on his way again. “It’s a shame,” Capello said, according to Football Italia. “He could have done a lot more in his career. I hoped he would mature after the birth of his son but, unfortunately, it’s the same old story. He’s a good kid, generous, but he doesn’t understand that there are limits. When he lets loose, there is no stopping him.” 

Few clubs now seemed willing to gamble on Cassano. When Parma signed him in 2013, the president, Tommaso Ghirardi, said people were calling him mad. But Cassano knuckled down and struck twelve league goals to lift Parma to sixth. Perhaps the World Cup motivated him: he had never played in one and, in March, he begged Prandelli to take him to Brazil. Prandelli did, and used him as a sub in two games in Brazil. But Italy crashed out of their group and Prandelli resigned on the spot. Cassano has not played for Italy since. 

Back at Parma, things went downhill. Financial turmoil hit the club and, amid a desperate relegation battle, Cassano left. In 2015 he returned to Sampdoria, but a year later new coach Marco Giampaolo left him out of his plans. Cassano still wanted to stay, but the president, Massimo Ferrero, told him to “get lost”. Having terminated his contract in January 2017, Cassano then joined Hellas Verona last summer. Seven days later he announced his retirement, saying he lacked motivation. On the very same day he reversed the decision. Another week later, he reconfirmed it. “The spark simply did not ignite with Hellas,” he said. “It’s like being with a woman and realising you don’t want to spend time with her.”

In August last year, Cassano denied that he had retired. But he vowed that if he hadn’t found a good club by September, he’d hang up his boots. No suitable offer arrived in time. Later he seemed to backtrack, saying he’d play for free. “I can play until I’m sixty,” he joked. Reports have linked him to USA, China and Serie D. 

It appears unclear whether he will play again. Were Cassano to retire now, at thirty-six, his trophy cabinet would display two major trophies: a scudetto and a Spanish league title. The scudetto came in a season in which he arrived in January; the Spanish title was won not because of him, but in spite of him. He has never started a World Cup match. As for the Ballon d’Or, he never got close. 

Over the last few years, Cassano has appeared to lament his petulance. He told AS that only an idiot could have behaved the way he did at Madrid. He has admitted that, in his rows with coaches, they were right ninety-nine percent of the time. “When I worked with a rigid tactician, I’d rebel,” he told Mediaset, according to Football Italia. “When I had a soft coach, I’d take a nap.” He has also saluted some of his ex-coaches, such as Allegri, whom he admires for his strong character and temperament. “People like that win,” Cassano said. “But those who are a bit out of their heads, like me, never win anything.”

Yet when asked about his biggest regret, Cassano does not answer Roma, Madrid or the Ballon d’Or. He brings up the row with Garrone. The two would reconcile before Garrone died in 2013, but Cassano never quite seemed able to forgive himself for it. That his main regret centres on a relationship, rather than his trophy haul, seems to echo what he put at the end of his book ten years ago. “What makes someone happy isn’t victories, or even money, but real affection,” he wrote. He added: “I’ll never be able to measure my happiness by the number of league titles I have at home.”

Home for Cassano is now his beloved Genoa, where he lives with Carolina and his two sons, Christopher and Lionel. He might yet sign for a club, but it has to nearby—he wants to be close to his family. Speaking to Corriere dello Sport earlier this year, Cassano said that he now gets up at seven, takes the kids to school, then trains. After breakfast, he trains again; then he picks up the kids at school. They play together until dinner time. “My life is marvellous like this,” he said. 

It sounded like the life he envisaged ten years ago, when he had just met Carolina. “With the calm and love she gives me, I’m another person,” Cassano says now. He believes that, had he met her at twenty, he’d now have a Ballon d’Or. But late is better than never. “I am lazy and I never did anything to get the best out of myself,” Cassano says. “But in life you have to be happy, and I am.”