Antonio Cassano, the fiery Italian striker who turned 44 on July 12, 2026, has never shied away from his reputation as a problematic figure. He openly admitted to being a difficult character, a sentiment shared by former managers like Fabio Capello at Roma and Real Madrid. Cassano once infamously told Capello, 'You're a piece of s***, you're more fake than Monopoly money.'
Cassano's Sexual Conquests and Hedonistic Lifestyle
Cassano boasted of a storied love life, claiming to have bedded between 600 to 700 women by his mid-20s, including celebrity flings. 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, contributed to his career challenges. In his autobiography 'Dico Tutto' (I'll Tell Everything), he recounted an arrangement with a hotel waiter who would bring pastries after his sexual encounters. 'In Madrid I had a friend who was a hotel waiter. 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,' Cassano wrote.
Rise from Poverty to Football Stardom
Cassano's journey began in poverty in Bari, raised by a single mother after his father abandoned the family. He emerged as a street footballer and secured a spot in Bari's first team in 1999. At age 17, playing against Inter Milan in Serie A, he introduced himself to the world with a stunning play: controlling a 40-yard pass with his heel, weaving past defenders Christian Panucci and Laurent Blanc, and dummying goalkeeper Fabrizio Ferron before scoring. Fans christened him 'El Pibe de Bari' (The Kid from Bari), a nod to Diego Maradona's nickname. In his autobiography, he reflected on that game: '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. That game my talent shone, and it took me away from a future of potential s***.'
Controversial Tenure at Roma and Real Madrid
In 2001, Cassano transferred to Roma for £26 million, becoming the world's most expensive teenager. He was twice named Serie A Young Footballer of the Year but clashed with managers and teammates. During the 2003 Coppa Italia final, after receiving a red card, he made 'the sign of the devil horns' at the referee. He told manager Luciano Spalletti, 'You're not coaching those useless players you had at Udinese. This isn't your house, it's my house.' After disputes with teammate Francesco Totti over a TV appearance payment, Roma sold him to Real Madrid for £4.4 million in January 2006. At Madrid, Cassano's weight issues led to fines, earning him the nickname 'El Gordito' (The Little Fatty). When Capello became manager, their past conflicts resurfaced. Cassano recalled an 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 led to a suspension, and Capello coined the term 'cassanata' meaning 'doing a Cassano.'
Later Career and Health Scare
After a loan to Sampdoria, Cassano joined AC Milan in 2010. He suffered an ischaemic stroke after a match, struggling to speak and feeling dizzy. He recalled, '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.' After surgery to correct a heart issue, he returned in April 2012, admitting he feared death. He later played for Inter Milan, Parma, Sampdoria, and Hellas Verona before retiring in 2017. He briefly unretired in 2018, spending a week at Virtus Entella before quitting for good, saying, '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.'
Feud with Cristiano Ronaldo
Now a co-host of the football podcast 'Viva El Football,' Cassano continues to court controversy. He criticized Cristiano Ronaldo's desire to score 1,000 career goals, saying, '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.' Ronaldo's sister hit back on Instagram, 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.' Cassano later claimed Ronaldo sent him a voice note after being left out of his top 10 players, listing his trophies and goals. Cassano replied, 'I just don't like you as a player. What's the problem?'
Legacy and Personal Life
Now happily married to water polo player Carolina Marcialis with two children, Cassano remains a sharp-tongued figure. His antics off the pitch have become cult folklore, and he still has the knack to stir up controversy, as evidenced by his feud with Ronaldo. Sampdoria president Riccardo Garrone once 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.'
