What annoyed me about Del Piero was precisely that he played abroad. I understood his idea behind it: he basically wanted to get to know Australia and he said he wanted his kids to grow up speaking English. His motives were fine. But I think it looks better when a player finishes his career at a top club. Del Piero playing for Sydney was kind of ridiculous.
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I'll tell you what's the difference between Totti and Del Piero since you gave an example few pages back.
Totti's kept renewing his Roma's contract until he was 40 years old and played his last match.
Thing is Ale did want to play for one more year and indirectly asked for that when he even said he'd sign another blank contract and play one more season for Juve and he was already on a huge pay-cut, Conte and Agnelli mainly didn't want him probably because his influence and authority in-between the fans is more than anyone and they thought it would be best to not renew his contract.
Del Piero was 38 when he left for Sydney, I'm pretty sure had Spalletti pushed Totti out at 37-38 he would have played at least one or two more years abroad.
Agnelli should have acted like a gentleman for a man and a legend who gave everything for the club and was the first to commit himself to Serie b, if he asked for one more year just give him that because at the end even if Conte is stupid he can't have the likes of Anelka, Bendtner, Matri,and be convinced that they'd give the team more than Alex but like I said I think it was personal.
However, his fair share time at Sydney wasn't bad, after almost 20 years at Juve he wanted to try something different and looking at the circumstances and how he was the biggest legend to play in Australia, it's more than fine in my book.