Actually if you read chapter 619 Hiruzen clearly says that AFTER forcing him to kill his clan we EVENTUALLY had him watch over Akatsuki as a spy. Itachi joined Akatsuki after the uchiha massacre, unless it was a translation error.Didn't think about this. It is possible that Itachi was with the Akatsuki sooner than what was revealed. He could have been apart of Konoha and the Akatsuki at the same time. But if not, then OP is right, it's definitely a pothole by like others above me have said, it's not a relevant one.
I even gave the image in the OP.
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