No. Ancelotti WAS stupid
He then had the straight-jacket of Sacchi's footballing ideas controlling him. Henry was his second mistake after releasing Zola at Parma. They turned to be two of the greatest players in EPL history.
Would Ancelotti let a player as talented as that escape him now? Maybe but I'd say there is more chance a Capello or Mourinho would. Ancelotti footballing philosphy has changed since then. A coach who managed to create harmony with a Milan team consisting of Rivaldo, Rui Costa, Seedorf, Pirlo and then later Kaka and utilising strikers such as Inzaghi and Crespo isn't the same man.