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Most of what attracts football fans to the beautiful game is all a matter of personal preference and taste. For the dramatic, an individual moment of magic and unexpected brilliance to lead their club to a late victory delivers instant gratification. Tensions raised between two opposing sides in a heated derby will surely satisfy the thrill-seeker, or perhaps it’s in the mystery with which the choreography is prepared by the ultras of opposing outfits and the theatre behind their unveiling prior to kick-off.

Most romanticise about watching their favourite footballer take to the pitch for their beloved team, embodying everything it means to put on the colours, signifying years of rich success, history, culture and memories; an eternal bond between connoisseur and club. Others, however, gravitate towards the varying characters and polarising personalities, and few garner more intrigue than Bari’s golden boy, Antonio Cassano.

Growing up without a father in the poverty-stricken San Nicola district of Bari Vecchia, young Antonio and his mother were left to fend for themselves. Thick-skinned and tough as nails, as unfortunate as the situation was, Antonio made it his life’s mission to avoid becoming another victim of his environment and use his God-given abilities to seek asylum through the use of his feet.

Football, like so many before him, became Antonio’s calling. Roaming the slums, calcio became his meal ticket – literally – as he would bet on himself against the older local kids in the ghetto in order to afford his bread for the day. Eventually, a local Bari scout spotted the young fantasista, granting the ambitious Italian his breakthrough as he climbed through the academy ranks to make his first-team Serie A debut at 17 in December 1999 against local rivals Lecce. It wasn’t long before the talented Barese attacker would send shockwaves throughout the peninsula.

Technically creative and full of pure imagination, il Gioiello di Bari Vecchia (The Jewel of Old Bari) lifted the San Nicola in just his second match, pulling off a sequence only a few footballers could emulate. In the 89th minute, a sprinting Cassano latched onto a 40-yard long ball over the top just past the halfway line, delicately controlling it with the outside of his right foot before a soft head-poke led him into space. With Inter defenders Christian Panucci and Laurent Blanc converging to close him down, Cassano swiftly weaved between them and slotted home past Fabrizio Ferron with a tidy, near-post finish to sink the Nerazzurri 2-1.

The mid-December thriller, as we’d discover nearly a decade later in his 2010 autobiography Dico Tutto (I’ll Tell You Everything), kept him from heading down the wrong path. If it wasn’t for that game against Inter I would have become a thief or worse; either way, a delinquent … that game my talent shone, and it took me away from a future of potential shit.”

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Fascination with ‘Fantantonio grew rapidly. Immediately, there was a uniqueness with which he combined an unhinged personality with his large bag of tricks capable of winning a match single-handedly. But, if he wished to be an all-time great alongside Roberto Baggio, his volatile personality would have to not derail what promised to be a long, glorious career.

Following two seasons with I Galletti, at 19 years old he headed to the capital to sign with Fabio Capello’s reigning title holders Roma for a transfer fee of 60 billion Italian lire (roughly €30 million) – the most expensive teenage signing at the time. Alongside the iconic Francesco Totti, Cassano became one of the Giallorossi’s most dynamic players, but it was clear early on that Capello’s biggest challenge wasn’t whether he could tap into his limitless potential or not. Rather, could he tame the teenager’s temperament enough to do it?

Cassano bagged five goals in his first season, winning Serie A’s Young Footballer of the Year award, yet the troubled teen found himself in hot water regularly during his Roman adventure. Feuding with Capello for being dropped after flashing the horns at the referee following a sending off in the 4-1 Coppa Italia final defeat to AC Milan, the playmaker would take his bad-boy reputation to Spain, signing for Real Madrid in January 2006 for a meagre €5 million.

Football and the allure of playing for Los Blancos in the Spanish capital along the likes of Raúl, Zinedine Zidane and David Beckham should motivate any young footballer enough to strive for excellence. For Cassano, however, his playboy lifestyle prevailed and ultimately defined his time in Madrid. Endless parties, poor eating habits – earning him the nickname ‘El Gordito’ for his cumbersome frame – and hundreds of sexual encounters disrupted his being.

Complete carelessness and a noticeable lack of desire made Marcello Lippi’s decision to exclude Cassano from his 2006 World Cup Italy squad quite simple. With the Azzurri historically lifting their fourth title at the Olympiastadion in Berlin, Cassano could only look on from his couch, perhaps reflecting on how he had let the dream of national triumph slip through his grasp.

Capello returned for a second stint as Real Madrid manager for the 2006/07 campaign, severing ties on a relationship with Cassano that’d been broken beyond repair. Later, acting president Ramón Calderón explained the Italian forward “showed a lack of respect” to the club and Capello, who invented the term cassanata – meaning ‘doing a Cassano’ – due to his explosive personality.

The city of Genoa proved to be a sanctuary for Cassano in the middle of the decade – at least for a few years – as Sampdoria took him on loan in August 2007. Fitness levels returned to normal and Cassano emerged as a key figure in a side ready to make some noise in Liguria. Trademark flair, vision, ball control and a keen eye for goal (nine goals and six assists in 22 Serie A appearances) all came to the forefront for the Blucerchiati in his debut campaign, helping the club secure a UEFA Cup berth with a fifth-place finish under Walter Mazzarri.

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His successful season wasn’t without controversy, however, as he was slapped with a five-match ban and a €15,000 fine in March for throwing his shirt in disgust after being sent off against Torino. Nevertheless, owner Riccardo Garrone acquired him outright on a free transfer, a flyer worth taking – all things considered – given his disciplinary record. Cassano’s outbursts seemed to have curtailed temporarily, and he was handed the role of vice-captain to Angelo Palombo. It was an indication that perhaps he had turned the page and would finally allow his boots do the talking.

Together with the arrival of Giampaolo Pazzini from Fiorentina in January, he formed a lethal partnership that spearheaded the Ferraris’ tenant to a Champions League berth. Garrone compared them to the renowned duo of Roberto Mancini and Gianluca Vialli that led the club to their only scudetto in their history in 1990/91. Later, Cassano’s refusal to attend the team’s awards night sparked a nasty dispute with Garrone that once again ended with an ugly divorce as AC Milan provided him a way out, acquiring him in January 2011 for an estimated €3 million.

In two seasons with the Rossoneri, minutes were hard to come by. Zlatan Ibrahimović, Robinho and Alexandre Pato had each carved out important roles for the red and black chase for top honours under manager Massimiliano Allegri. Months after celebrating Milan’s 18th title, Cassano suffered a life-threatening moment in Rome in October 2011 after the club’s 3-2 win over his former side. Doctors later diagnosed Cassano with an ischemic stroke and he was operated on days later to correct the heart problem that had caused the occurrence.

The fear of dying, along with the outpouring of love and support from his peers around the globe, opened his eyes. Deep down, the hunger to return and be remembered for his work on the pitch was cultivated. Five months after going under the knife, Cassano stepped back onto the pitch as a substitute in a 2-1 loss to Fiorentina. Healthy, fit and motivated, the boy from Bari earned a surprise spot in Cesare Prandelli’s Euro 2012 squad, forging an alliance up front with a man who was no stranger to some controversy of his own, Mario Balotelli.

During the competition, the 29-year-old was back in the headlines at a press conference for all the wrong reasons. When asked if he thought Prandelli’s Italy roster included any homosexuals, Cassano replied: “I hope there are none.” Sparking outrage and protest from gay rights groups, Cassano insisted the media had misinterpreted his words. Later, he would apologise, retracting his statement, saying: “I sincerely regret that my statements have sparked controversy and protest from gay rights groups. Homophobia is a sentiment that is not mine. I did not want to offend anyone and I cannot question the sexual freedom of other people.”

UEFA would fine the Italian €15,000 for his comments, yet that did not deter Cassano from delivering a string of stellar performances for his country that month in Poland and Ukraine. Wearing the number 10 shirt, Cassano’s greatest abilities permeated his six matches in the tournament, sending shockwaves throughout his country back home. Though his lone goal arrived against Ireland in the knockout stage, it was his ensemble in the semi-final thriller where his exploits won over many of his biggest critics. Supplying Balotelli with his first of two goals to sink Germany 2-1, Cassano’s stunning performances helped Italy punch their ticket to the final versus Spain where they eventually lost 4-0.

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Following the summer, AC Milan’s fire sale of Ibrahimović and Thiago Silva forced Cassano to seek refuge elsewhere as Silvio Berlusconi attempted to balance his finances. City rivals Inter were keen to bring him aboard for the 2012/13 season, striking a deal with Milan involving cash plus Pazzini. His Nerazzurri spell would be short lived, however, lasting one season as constant clashing with manager Andrea Stramaccioni created a toxic environment for the Milanese side that finished ninth.

Cassano’s Italian tour continued in July 2013 as a move to Parma brought out the best he had to offer; working hard, maintaining a proper physique and keeping controversy to a minimum. Finding top form in 2013/14, gaudy tallies of 12 goals and eight assists were of paramount importance in the Crociati’s Europa League berth, finishing sixth. Months of unpaid wages due to Parma’s financial standing – and eventually seizure of all property and declared bankruptcy – saw Cassano’s contract terminated.

Looking for a place to hang his hat, Sampdoria welcomed him back in August 2015 on a two-year deal. A year later, president Massimo Ferrero communicated that Cassano was no longer part of the project, and from there, he trained with the club’s youth team before parting ways entirely in January 2017. A free agent in his mid-30s, several rumours hinted a move to China could be in the works, a journey which Cassano had no interest in travelling.

Earlier this summer, Hellas Verona struck a deal to reunite the 35-year-old with Pazzini in an attack that also included Alessio Cerci. Verona, now back in Serie A after earning promotion from the second division, received widespread praise for forming this faction of Italian talent. Yet, as we’ve been privy to over the course of his career, wherever Cassano goes, controversy tends to follow.

On 24 July, weeks after signing for Verona and taking a massive u-turn that spurred widespread publicity, Cassano communicated his retirement – for the second time – prioritising his family over football. In the aftermath, his wife Carolina Marcialis hinted on her social media profiles that Antonio would be looking for a new club, which was later clarified by the player himself. “Carolina was wrong, after thinking and reflecting in the end I decided. Antonio Cassano will not play football any more. I apologise to the city of Verona, to all the fans, to the president. For a 35-year-old man I need to be motivated and at this moment I feel that my priority is represented by being close to my children and my wife.”

Blessed with a bevy of talents, Cassano’s early demonstrations emblazoned the Italian peninsula. Possessing the means to be one of the best Italian footballers of his generation, there was no disputing his talents. From rags to riches, his rise from the harsh ghettos of Old Bari to the main stages of calcio inspired many back home. But, sadly, most of what Cassano produced on the pitch, and off it, will have left a lasting impression on the football world, asking “what if?”

By Matthew Santangelo