Well, there are a few things to consider.
Del Piero has earned it.
Del Piero would be a backup.
Cassano is more influencial.
Cassano would be a starter.
Cassano, at this point in their careers, is the better player. And, would surely start over Di Natale, who I don't think is good enough to fill the trequarista role. However, Donadoni needs to determine if he wants to take a chance on Cassano, who could explode at any minute. Or try to get by with the must respected and always dedicated Del Piero.
I am a fan of both players. I would take Cassano. But, it would be nearly impossible to not select Del Piero. Quite frankly, since we have so much versatility in defense, I would take them both.
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