Information Broker Sai
(Note: This entry was not made to resemble the reference image from foot to toe. So i'll explain why certain items are in there. Also.. I'll admit this is the worse submission i've done so far)
-The crow: It's there since one of Itachi's signature descriptions is that he likes to use Genjutsus/Ninjutsu that usually involve crows for what ever reason.
-The dust and facial expression - I just wanted to try add the effect that Itachi portrays at times.