The Controversial And Confusing Career Of Antonio Cassano Reaches The Perfect Conclusion

As the first words were placed onto this page, Antonio Cassano had rethought his recent decision to retire. He was set to play another season at Hellas Verona, reuniting with Giampaolo Pazzini for a Serie A farewell tour. By the time we got to the final words of this very paragraph — barely the third sentence — he was going to retire again.

By the time you’ve finished this article, the circumstances may well have changed. But as of Monday morning, Italian time, Cassano has once again decided to retire. According to Sky Sports Italia, the reason is the time and distance playing in Verona puts between Antonio and his family.

At one point in Cassano’s career, sex and pastries were the main motivating factors. Clearly, this is a sign he has grown up. Thankfully, it gives us time to talk about Cassano and his wonderful career.

In his autobiography, Cassano decided to start his story with his debut Serie A goal, scored against Inter Milan. Well, technically, he starts with the aftermath of the match and the party that followed. But that goal was incredible. One of the greatest first touches in the game. Born and raised in Bari — right on the heel of the Italian boot — Antonio Cassano had just begun to stake his claim for a first team place.

That night, in December of 1999, with Antonio Cassano just 17, Bari and Inter are locked into a draw. It’s the closing minutes of the second half. A long ball is launched from just outside the Bari box. It sails over the Inter Milan midfield, falling ten yards into the opposition half, where the teenage striker is lurking, doing his best to occupy two defenders.

As the ball loops overhead, Cassano is already in his stride. Without pausing, he casually reaches his right foot behind and cushions the ball with the outside of the boot. The immaculate touch instantly brings the ball into the player’s orbit.

Having used his first touch to knock the ball over his sprinting shoulder, Cassano jerks his neck and nods the ball into his path. This happens in the space of half a second, while the Inter defense is still coming to terms with that first touch.

But Cassano is now straight through on goal. The keeper is encroaching, edging out to meet the striker. The two defenders are hurdling toward the teenager. And Cassano stutters. It’s not quite a dribble. It’s a pause. A caesura. As a result, the goalkeeper is suddenly filled with doubt, caught in no man’s land. The two defenders, unable to change their direction, collide with one another. Cassano, meanwhile, deftly steps between the two, takes a step to the side and slots home.


It was the match winner, a stunning way for the youngster to announce himself on to the stage of Italian football. It was a perfect moment, crystallizing the raw talent, ingenuity and charisma which would mark all of Cassano’s greatest goals.

Antonio Cassano is the author of a million amazing moments. But to write his hagiography is to hardly talk about football. A career filled with the bitter tragedy of unrealized potential, this story is Shakespearean in its depth of tragedy; the pathos of the pastry-loving boy from Bari.

From bribing bellhops to sneak women out of (and pastries in to) Madrid hotel rooms, to being the one man who could get under the skin of Fabio Capello like no one else, this single article will do nothing to justify the career of one of Italy’s brightest stars. So, let’s take an episodic approach, reviewing some of Cassano’s greatest moments.

Understanding the career of Cassano is — in part — understanding the regional divides of Italy. Growing up in one of the poorest regions in the country, raised by a single mother in abject poverty, it took 19 years before Roma moved to make Cassano the most expensive teenager of all time. They spent 60 billion lire, roughly €30 million. It was an extraordinary sum for an extraordinary talent, indicative of the amount of money that was flowing through the Italian league around the turn of the millennium.

But the sheer contrast between the beyond-humble beginnings and the bright lights of the ancient capital can potentially explain how readily Cassano went off the rails.

Fabio Capello is one of the most respected coaches in the world. While Cassano was happy to row with anyone, he took a special glee in being able to wind up the Roma coach. It was a relationship described by the then-Roma player Oliver Dacourt as the “tough love” shared between a father and son. Sniping at one another, the player keen to ditch training at any time, the two were a tinderbox waiting to ignite.

Capello would chase Cassano around the training ground, demanding to know why he didn’t run as quickly during matches. “Anarchy is always just around the corner with Cassano,” Capello admitted. The two came to blows. But it didn’t stop the coach signing the player again while managing Real Madrid.

The time at Roma was probably Cassano’s most successful. A quick YouTube search can bring up the time he shared on the pitch with Totti, the two capable of fantastical acts of imagination when playing together. Cassano won trophies and was named the best young player of the year on two occasions. But he managed to fall out with the management and was shipped off to Madrid for €5 million, in part due to the six months left on his contract. This would become a feature of Cassano’s career.


The time at Real Madrid, as described in his biography, was the time of Cassano’s greatest debauchery. Further away from Bari than ever before, in a foreign culture and at one of the biggest clubs in the world, he let himself go.

As mentioned above, he came to an arrangement with a Spanish bellhop. After bringing a girl back to his room, he would phone the bellhop. The friend would then come to the room, escort the woman from the hotel, and bring — in her stead — a selection of pastries. Cassano would then gorge himself. At one point, he was so big that the coaches were fining him for every gram he was above his ideal weight.

Later, Cassano would claim to have slept with over 600 women, though it seemed food remained his first love. After retirement, he admitted, he would allow himself to become incredibly fat. At Madrid, it seemed, he was close to semi-retirement.

At Madrid, the relationship with Capello was under even more scrutiny. Nicknamed Cassanata by Capello (a portmanteau reference to the player’s “madness”), the press was well-aware of their combustible bond. Television cameras managed to pick up on Cassano doing an impression of the boss, undermining the coach’s authority for all to see.

Eventually, as Madrid cycled through coaches, Cassano was banished to the reserves. There, he got to train with David Beckham, who happened to be exiled for entirely different reasons.

After departing from Real Madrid, Cassano found himself having something of a renaissance. Returning to Italy seemed obvious. But where? Sampdoria decided to take a punt on the out-of-favor striker. With Madrid paying the majority of his wages, Cassano returned to Italy. Sampdoria, in Genoa, was far from Bari. But it was a port town. The team was far from the top of the division but the diminished spotlight seemed to suit Cassano.

In Sampdoria, he played some of the best football of his career, especially when striking up a partnership with Giampaolo Pazzini.

After three years of excellent performances and only the occasional argument, Cassano seemed to have grown as a person. He married a teenage water polo champion. He almost achieved consistency. He even managed to get back into the Italian national team, where he would eventually team up for a Euros run out with Mario Balotelli. But, almost inevitably, things came crashing down.

After refusing to attend an awards ceremony, Cassano was frozen out of the team and was almost fired. A complicated deal, including paying a buy-out to Madrid, dealing with the court of arbitration to potentially annul his contract and slashing the player’s wages, Cassano found himself on his way to Milan.

It was thought that Cassano could replace Ronaldinho, who had just left the club. They shared similar profiles both on and off the pitch. Milan won the title that season while Sampdoria was relegated. Cassano was playing with Ibrahimović and many of Milan’s other stars and was certainly capable of holding his own.

But, after playing against Roma in November of 2011, he suffered a stroke at the team hotel. Immediately hospitalized, no one knew the extent of the injury. At first, it was thought to be life-threatening. Then career-threatening. But Cassano fought hard against the heart condition and, after six months of recovery, was back to playing.

But he wasn’t at Milan for very long. Worried about the recent sales of Milan’s best players, he requested a transfer and was sent to Inter. In the other direction went his former strike partner, Giampaolo Pazzini. It wasn’t a good season. Cassano scored occasionally and argued with the coach, but he left after just one year.

From there, he went to Parma, back to the south of Italy. One good season at Parma was followed by a catastrophic season. Cassano left in January of 2014, allowed to terminate his contract early because he hadn’t been paid his wages for six months. In that time, however, he seemed to have been close to professional. Shedding weight and calming down, the problems at Parma were far from his making.


Since that time, it has been hard for Cassano to find his place. There was a brief return to Sampdoria, an attempt to rekindle the magic. But it didn’t work. Banished to the reserves after a year, Cassano was forced to rescind his contract. Which is how he arrived at Hellas Verona.

In recent years, Hellas has managed to bring in players in the twilight of their careers and make the most of them. Luca Toni, for instance, was fantastic despite his age. Hellas Verona even went so far as to sign Pazzini, taking a tribute act approach to Serie A’s greatest hits. Before a ball has even been kicked, however, things have fallen apart.

Last week, it was announced Cassano was set to retire. Finally, he would be able to sit around all day and eat cake, just as nature intended. But then, barely a day later, he announced that he had changed his mind and was going to play for Hellas after all. And then, just as this article was about to be written, news broke that he was retiring. Keeping track of Cassano can be impossible, at times.

We’ve barely even managed to scrape the surface of the Cassano story. We’ve not touched on his relationship with the national team, the vague parallels to Mario Balotelli (and why they are very different), or the ways in which class and regional differences are portrayed on the stage of Italian football. The story of Antonio Cassano is one of the great stories of Serie A. Occasionally magical, frequently tragic. Always fascinating.

As we get to the final words of this article, it has already emerged that Cassano has not actually retired. Instead, he’s just quit Verona. He might even sign for Genoa. By the time you read this, the story will have changed at least three more times. Even if he doesn’t retire, it’s hard to imagine a more fitting end to the career of Cassano. Controversial, confusing and mercurial to the very end. And all the better for it. 

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