Cassano is a brilliant player. But comparing his assists stats to those of a central midfielder is a little short-sighted + pointless in this debate. Pirlo has shown quality throughout his career. For Milan, for Italy and now for Juve. What did these teams have in common? They were built on systems that maximized Pirlo's skillzzset and covered his shortcomings.
I think a lot of false opinion has been taken as fact all through Pirlo's career on these boards. First there was the myth that Pirlo couldn't play without Gattuso. Safe to say, thats gone out the window. Then second there's the false opinion that Pirlo "didn't give a shit" after Athens 07. While he may not have been as motivated throughout a season as before, he was pivotal for us getting past the group stages in 07-08 + remember that European Super Cup? Carlo's last season saw a rare case of him being injured for a long spell, and I thought he did play well under Leo. Certainly he and Clarence were our standout performers in the middle.
The problem with Milan was that we had Ambro/Gattuso and co. pushing forward, while Pirlo stayed back deep. It didn't make sense to have him play there anymore. So yes, bringing VBoss into the fray helped us experiment for half a season. And while VBoss started well, he made quite a few errors towards the end of the season. And in fact, while a lot of people here give him credit for that Scudetto, Clarence post Spurs was simply BOSSing the midfield.
This season, VBoss has been missing a step ... Clarence hasn't had any sort of continuity. Noce has been an average signing (still a very good one by the way) and Aquilani hasn't showed up. Few cameos here and there, but nothing consistent.
We should have thought it clearly. We were replacing a player who guaranteed consistency. He had been playing a lot throughout his Milan career, being injured 2-3 times for long spells during the space of a decade. VBoss couldn't give us this, and a few of us (me) saw this all the way from last season.
Our midfield is in shambles, especially now with VBoss going. I just hope Monty steps up to the plate as I wouldn't mind him playing the anchor role and us going back to the DLPBS. As getting a quality anchor would require another quality b2b creative CM to play opposite Monty.
That will be expensive, but even better (and more expensive) would be to push KPB into RCM + buy a quality AM.
Thing is, whoever we bring in, we need to get something resembling continuity in central midfield. They way how Pirlo, Gattuso, Ambro and Clarence used to seamlessly switch roles and positions in midfield was a joy to watch. They knew each other so well because they played together for so long. This should be our aim and target as we look to rebuild perhaps the most important part of our team ... the midfield.
BOSS 
The reason why we didn't win anything post 07 
