Quote Originally Posted by DB_Hunter View Post
His goal was to make Sasuke strong and proud of his clan, without having any idea the village was to blame for anything. This was successful throughout and only backfired because Itachi didn't realise that Tobi knew about the whole thing and would be able to tell Sasuke, as Itachi comments to that effect in the last couple of episodes.
It also wouldn't have backfired if the entire plan didn't revolve around turning his brother into a revenge-obsessed hate-filled piece-of-shit and then just crossing his fingers and hoping that mess would end up pointed in the right direction.

Worst. Plan. Ever.