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I agree with the point about Carletto's job being made more difficult when players are brought in that don't necessarily fit tactically or that are in because the owner (and not necessarily the coach) wants them in -- ie, Sheva and Ronaldinho.
As for coaches and experience, It's a cointoss in my opinion. Sure, a lot of folks would want someone with real experience in winning lots of titles (my fantasy choice here would be Capello). That said, a couple of Milan's very best coaches had very little coaching experience and no titles to their name when they came to Milan -- Capello and Sacchi. So...
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