Italian football's enigmatic Antonio Cassano is rumoured to be on his way to Milan, a place where he could resurrect a career that has never really gotten going.
Sampdoria owner Ricardo Garrone has been intransigent on the issue since October. Such is his conviction that he has even sought legal recourse. You could say, he is a man who is willing to take a stand in Italian football, where shifting allegiances, caprice, corruption and panic dictate the terms of administerial conduct.

It has taken Antonio Cassano, the celebrated and maligned pariah of Italian football, to inspire a modicum of consistency in Italian football, a philosophical stand that should cause pause for thought amongst people like Palermo owner Maurizio Zamparini, who changes his mind about issues twice every mood-swing.

The senescent Garrone nurtured Cassano at Sampdoria; his paternal shadow fostered the 28-year-old’s undeniable talent and deprived the same player’s tempermental side of light. Cassano seemed to be finally fitting in. Even his press-conferences were about the wonders of marital stability. Alongside relinquishing promiscuous sex--he boasts of having slept with over 600 women--Cassano seems to have also given up his intractable self. The performances on the field bore all this out, for Sampdoria and for Italy. There were no more Cassanetas, the much vexed hysterics to which he was so prone, which have heaped ridicule on the player for years.

Then, the calm broke. It emerged that Cassano had fallen off the wagon. The events are still obscured by the reluctance of witnesses to come forward, but what is certain is that Cassano brutally insulted Garrone when asked to attend a local awards ceremony.

Even allowing for Garrone’s patience, this was a step too far. Cassano went public with apologies but to no avail: he was frozen out of the Sampdoria team, and Garrone took the matter to the arbitration panel in an effort to have Cassano’s contract rescinded. He was unable to win the case definitively, as Cassano was ordered to be reintegrated into the team on February 1st with his wages halved for the remainder of his contract.

It seemed that Cassano’s sale was always inevitable, but the question is which club in Italy can accommodate the player’s massive ego. The prime minister’s it seems.

Earlier on Thursday it appeared that Garrone was willing to offer the player a way back into the team, but latest reports have revealed that Milan vice-president Adriano Galliani reached an agreement with Beppe Bozzo, Cassano’s representative, over dinner. The agreement, which would be made official during the January transfer window, would see Cassano earn 3 million euros a year until 2014. The only potentially stumbling block is the 5 million euros that have to be paid to Real Madrid since the Spanish club stipulated such a pay-out in the event that Sampdoria decide to sell their former player.

Milan are the unique club in which Cassano can flourish. For starters, the club does not brook dissent. Like it or not, Milan is a projection of Silvio Berlusconi, a borderline autocract whose peccadillos, scandals, and alleged crimes have done nothing to weaken his authority at the club. Milan is his ideological register, which he has often used to gauge and influence public opinion. And he always keeps you guessing. The sale of Kaka’ in 2009 was supposed financial solidarity with a country in recession; the summer purchases of Zlatan Ibrahimovic and Robinho were well-timed gifts to Milan fans who bristled at the newly found commitment to financial responsibility.

The Cassano deal came two days after Berlusconi barely survived a no-confidence vote in the Chamber of Deputies. Perhaps in the euphoria of recording yet another narrow victory or in the hope of deflecting attention from his precarious political position, Berlusconi has decided to splash the cash once again.

Just ask Milan’s coach of last season, Leonardo, what he thinks of Berlusconi. “Narcissus does not like anything that is not a reflection of him,” he said of Berlusconi, an elegant response to the owner’s sustained and unjustified attacks on the coach. Of course, Berlusconi still looms large over the club, while Leonardo, who was a loyal servant for 13 years, left.

Berlusconi has already given Cassano a lukewarm reception by stating that he thinks “Ronaldinho is better.”

Due to, and sometimes despite, Berlusconi, Milan have a singular prestige in Italy that even Juventus finds hard to rival. The Rossoneri have won the European Cup seven times, which still staggers Inter and Juventus. Further, it also seems that both Inter and Juventus, though huge clubs in any sense, do not have the environment to contain Cassano. Under Luciano Moggi Juventus certainly did. However, the current administration can barely conceal disagreements. The recent one between Gianluigi Buffon and coach Gigi Del Neri being one.

Inter, on the other hand, have never been a club with an extraordinary amount of discipline. Jose Mourinho changed that for a couple of seasons, but Inter are busy collapsing in their own peculiar way under Rafael Benitez. Also remember, this is a club that compels its former star Christian Vieri to sue the owner for having his phone tapped.

Crucially, Cassano will not be working as the only star in Milan. Despite the presence of the icon Francesco Totti, Cassano felt that he could behave as he wanted at Roma, as the sole prima donna in the squad. Then coach Fabio Capello had little time for his antics. At Sampdoria, where he ended up after a forgettable stint at Real Madrid, perhaps only Giampaolo Pazzini came close to matching Cassano’s impact on the club. At Milan, he will be playing alongside Champions League and World Cup winners, and the likes of Robinho and Ibrahimovic. It is hard to see how he could possibly misbehave and not look like a colossal idiot.

If Milan end up signing Cassano, they could give him exactly what he needs: the environment for his skill, not his attitude, to assert itself. At 28, it appears this is Cassano’s last chance.