FOOTBALL MAVERICKS One of the most talented footballers of his generation could never stay out of trouble, whether he was clashing with managers or bonking 700 women
One of football’s most controversial stars never shied away from acknowledging his own complexity, openly confessing he was “a problematic guy”.
Antonio Cassano’s candid assessment was a statement that many, including his former manager Fabio Capello at both Roma and Real Madrid, might readily agree with. In an infamous exchange, the fiery Italian striker didn’t hold back on his feelings, telling the legendary boss: “You’re a piece of s***, you’re more fake than Monopoly money.”
While such emotional volatility is just the tip of the iceberg in the enigmatic tale of Cassano, his other indulgences, particularly sex and food, have been sources of controversy as well. Cassano – who turns 44 today, Sunday, July 12 – boasted of a storied love life, claiming to have bedded between 600 to 700 women by his mid-20s, celebrity flings included.
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And he asserted that he “played a great match after having sex”. His hedonistic escapades in Madrid, where he indulged in both soccer and sensual pleasures, played their part in his career challenges.
The prodigiously talented but hotheaded Italian merged his twin passions with a gusto that ultimately spelled trouble. The rollercoaster journey of Cassano took yet another swerve when he announced his retirement unexpectedly, just a week into training with a new team.
Taking a deeper look into the madcap world of Cassano offers insight into his journey from poverty in Bari, raised by a single mother following his father’s abandonment, to gaining distinction as a street footballer and eventually securing his spot in Bari’s first team in 1999, impressing swiftly.
The story of Cassano’s rise in football reads like a movie script, marked by a pivotal moment that changed the trajectory of his life. At just 17 years old, playing in Serie A against none other than Inter Milan, he introduced himself to the world of football with a play that left fans speechless.
He masterfully controlled a long 40-yard pass with his heel on the run, weaved past defensive legends Christian Panucci and Laurent Blanc, then coolly deceived goalkeeper Fabrizio Ferron with a dummy before striking at the near post. It was abundantly clear: Cassano had arrived.
Quickly embraced by fans, he was christened El Pibe de Bari (The Kid from Bari), a nod to Diego Maradona’s own nickname, El Pibe de Oro (The Golden Boy). His raw talent promised a path vastly different from the grim alternatives of his youth; in his revealing 2008 autobiography Dico Tutto (I’ll Tell Everything), he reflects on the transformative power of that exceptional game against Inter.
“If it wasn’t for that game against Inter I would have become a thief or worse; either way, a delinquent. A lot of people that I know have become involved in that life,” he wrote. “That game my talent shone, and it took me away from a future of potential s***.”
His journey saw a meteoric rise when, at 19, he transferred to Roma in 2001 for a stunning £26m – earning him the title of the world’s most expensive teenager. During his time with Roma, his name became synonymous with excellence as he was twice honoured as Serie A Young Footballer of the Year.
But amid the triumphs, controversy haunted Cassano. A particularly heated spat with Capello caught the public eye after Cassano was sidelined from a practice match; insults were notoriously traded, both parties telling each other to “f*** off” more than once. Match officials weren’t spared from his fiery temperament either.
Perhaps one of his most notorious outbursts occurred during the 2003 Coppa Italia final against AC Milan where, after receiving a red card, Cassano’s frustration boiled over into a controversial gesture – “the sign of the devil horns” directed at the referee, an image forever etched in Italian football history.
Luigi Delneri, Roma’s then-manager, took a no-nonsense stance by dropping Cassano from the squad. But Bruno Conti, his successor, welcomed him back and even made him captain – a move that likely gave Cassano a sense of empowerment.
However, when Luciano Spalletti took over in 2005, he faced Cassano’s defiance as the player told him: “You’re not coaching those useless players you had at Udinese. This isn’t your house, it’s my house.”
Cassano’s attitude led to conflicts within the team, including a heated dispute with team-mate Francesco Totti over payment for a TV appearance.
With tensions high and contract renewal talks stalling, Roma decided to cut their losses and sold Cassano to Real Madrid for a mere £4.4m in January 2006.
In Madrid, Cassano indulged in his playboy lifestyle, which he candidly described in his autobiography. He recounted an arrangement with a hotel waiter who would exchange pastries for Cassano’s female companions post-encounters.
“In Madrid I had a friend who was a hotel waiter,” he recalled. “His job was to bring me three or four pastries after I had sex. He would bring the pastries up the stairs, I would escort the woman to him and we would make an exchange. He would take the girl and I would take the pastries. Sex and then food, a perfect night.”
But Cassano’s indulgences in sex and food ultimately contributed to his downfall, as Real Madrid started fining him for every gram he was overweight, earning him the unflattering nickname El Gordito (The Little Fatty).
Things took a turn for the worse when Capello replaced Juan Ramon Lopez Caro as manager and their previous disagreements in Rome resurfaced. In his book, Cassano recalled a specific incident at Tarragona: “He made me and [Brazil legend] Ronaldo warm up the whole second half without putting us in.
“In the locker room I told him ‘You’re a piece of s***, you’re more fake than Monopoly money'”.
This disrespect towards Capello resulted in a suspension. Around this time, the manager coined the term “cassanata”, meaning “doing a Cassano”.
The player expressed his desire to return to Roma, even hinting at a reconciliation with Totti and the club’s management. Eventually, he was transferred to Sampdoria, initially on loan, with Madrid’s then-president Ramon Calderon describing his attitude as “unsustainable in the last couple of months”.
Despite occasional outbursts of anger or petulance, Cassano was relatively well-behaved during his three years at Sampdoria. However, true to form, his time there ended on a bitter note.
After refusing to attend an awards presentation night, Cassano found himself in a dispute with the club’s president, Riccardo Garrone. He attempted to terminate the player’s contract due to gross misconduct, but a tribunal decided to halve his pay instead.
Speaking to Tuttosport, Garrone said: “I’m very sorry because if Cassano didn’t have that temper, and if he was not a bit of a funny guy every now and then with no self-control, then he could have been one of the greatest players in the world.”
After joining AC Milan in 2010, Cassano managed to control his erratic behaviour, but then faced a harrowing health scare. Post-match, feeling unwell on the team bus, Cassano found himself struggling to speak coherently and was dizzy, symptoms that led to hospitalisation where he was diagnosed with an ischaemic stroke.
Recounting the events, Cassano revealed: “We argued for half an hour before I agreed to visit the hospital. And that is when I started to have trouble speaking and thought about seeing my son again.”
Following surgery to correct a heart issue after four days, he made his return to football in April 2012, confessing he had feared death: “If I am honest I was afraid of dying, in particular during those days before the operation.”
Spells at Inter Milan, Parma, Sampdoria and Hellas Verona followed, before Cassano announced his retirement initially in 2017. He backtracked on his retirement plans briefly in 2018, spending just a week at Serie C side Virtus Entella before hanging up his boots for good.
He said at the time: “Over the last few days of training, I realised that I no longer have the mentality to train consistently. In order to play football, you need passion and talent, but above all determination and at this moment I have other priorities.”
Now at 44, the man is happily married to water polo player Carolina Marcialis and they have two children. But, as they say, you can never keep a good dog down and Cassano continues to court controversy as a co-host of the football podcast Viva El Football. Don’t believe us? Just ask Cristiano Ronaldo.
The pair were locked in a war of words after Cassano offered some choice words about the Portugal captain’s desire to score 1,000 career goals.
He said: “Cristiano Ronaldo doesn’t know how to play football. He could score 3,000 goals, I don’t give a f***. [Gonzalo] Higuain, [Sergio] Aguero, [Karim] Benzema, [Robert] Lewandowski, [Zlatan] Ibrahimovic and [Luis] Suarez knew how to link-up with the team.
“They knew how to do a lot of things, unlike Ronaldo whose only objective has always been to score.”
Elma dos Santos Aveiro, Cristiano’s sister, hit back at Cassano’s remarks on an Instagram post, saying: “He doesn’t know how to score 900 goals. Imagine if he did. They say he was a footballer. I think they’re wrong. He was certainly a ball boy.”
The feud boiled over the following month when Cassano went on another podcast, The BSMT with Gianluca Gazzoli, and claimed that Cristiano took exception to being left out of his top 10 players of all time by leaving a voice note.
Cassano said: “I said Ronaldo is No1, the Brazilian. Cristiano Ronaldo doesn’t make my top five, or even top 10, because for me the quality of a player is another thing.
“Next thing, I finish the work I was doing and I get a text message from a +34 number – that’s Spain. It’s a list of all the trophies, goals and statistics.
“Then he sends me a voice note, telling me, ‘You disrespected me, don’t do anything like that again. You only scored 150 goals, you only won four trophies’. Perfect.”
He concluded by saying: “So I answer him. I say, ‘Dear Cristiano, listen to me. You think I disrespected you, I just don’t like you as a player. What’s the problem?’ He went to the trouble of messaging me. Imagine.”
Nearly a decade on from hanging up his boots, Cassano shows he still has the knack to turn up the heat in football. His antics off the pitch were the stuff of cult folklore. Now he cuts a more mature figure, but still maintains the sharp tongue that got him in trouble with Capello and, later, with Cristiano.