Now they are scratching their heads again after Juventus President Giovanni Cobolli Gigli has declared that the Turin giants are interested in 26-year-old Sampdoria striker Antonio Cassano.
"He is a boy that is fast becoming a man," Cobolli Gigli told Radio Anch'io lo Sport.
"He is a very good player. [Sporting Director Alessio] Secco has spoken of who could be bought in June and that of Cassano is a name of which we are thinking about."
If it were based simply on talent, Cassano would be considered one of the best in Italy. He was deemed the "future of Italian football" by former Italy coach Giovanni Trapattoni after his €28 million transfer from Bari to Roma in 2001.
However, he possesses one of Serie A's hottest tempers and isn't afraid to speak his mind when he thinks it's necessary.
There is no doubt that when he has everything clicking, he not only creates chances for himself, but also for his teammates.
It's the reason why he fell out with Fabio Capello at both Roma and Real Madrid and why he has a rocky relationship with Italy boss Marcelo Lippi.
He has kept his nose clean for a year after his famed tirade.
Add that to the fact that along with Amauri, Juve have Alessandro Del Piero, Vincenzo Iaquinta, David Trezeguet, and Sebastian Giovinco already in their ranks. Playing time would be hard to come by.
A hot temper and no guarantee of a spot in the starting lineup — a recipe for hotheaded Toto to explode again?
Then there's the financial issue.
Sampdoria executive Giuseppe Marotta recently said he will sell Cassano for €20 million. Yet after spending €20-plus million on Amauri last summer, would it really be logical to go ahead and shell out another figure close to that for yet another forward?
It's the same thing Juve fans asked themselves when they were on the trail to sign Amauri, and I'm not convinced that the Old Lady's fans want to go down that kind of path again for a player that plays a position that is already the deepest on the team.
Playing for a prestigious club such as Juve could help him continue his maturation process, but that was the same thing most thought was going to happen when he moved to Madrid. And we all know how that turned out — leaving the Bernabeu without saying a word to his former teammates.
And at Juve, if they keep Claudio Ranieri around next season (all signs point to yes if what the Juve hierarchy has said publicly lately), Cassano wouldn't have to deal with a dominating personality managing him like Lippi and Capello.
Yet it's February, and talk in the papers is just talk in the papers. If it happens to resurface when the summer transfer window is open, then we might have to take all this talk seriously.
Could the Old Lady use Cassano's creativity and flair? Absolutely. But would the risk really be worth the reward?
He might be seen as the potential heir to Del Piero's Juventus throne, but there is no way that Cassano will ever come close to being the same kind of class act as Il Capitano.