Thread:Omega64/@comment-4503935-20190703001710/@comment-10330822-20191130173246

Sai's whole deal with the summit was that he thought it was unfair to make Naruto go plead to the Raikage. It's not that he thought it was a bad idea or anything, just that it was unfair to him. Otherwise, I doubt Sai didn't believe that Naruto couldn't achieve what he was setting out to do, whether it was convincing the Raikage to spare Sasuke or still attempting to bring Sasuke back. So I don't think he felt Kakashi was wrong for at least giving Naruto the opportunity.

The main thing to remember with Sai is that he was only doubting Naruto's intensions. In other words, he didn't fully believe Naruto was doing this for himself and was rather just doing it for Sakura at his own expense.