Minato
Itachi
Kakashi
Minato and Itachi both had incredible insight and at least planned for a few things to go wrong in their ultimate plan. They both put some form of back-up into their plans (Itachi entrusting Naruto with Sasukes defection, using the crow to cast KA to "Protect Konoha") and Minato (storing a bit of chakra in case Kurama went awry). The only differences is that Minato achieved his desired outcome whereas Itachi didn't. The one area he failed to do is why I believe Minato goes on top. I also believe that under pressure, they both do a good job at identifying weaknesses in attack. Itachi with Chibaku Tensei, and Minato determining a way to land an attack on Obito.
And Kakashi is intelligent, but he hasn't had any long term plans. His analysis is on par with both. Battle tactics-wise, I believe they both still outclass him, but barely. It is possible he could analyze more about them than them him with how close they are together, but ultimately, still loses.
Minato's plan to save the world by sealing the Kyuubi into Naruto to fight Obito is still a work in progress, but is progressing.
Itachi's plan to have Sasuke be an honor to the Uchiha clan yet save Konoha actually ended in Sasuke being an international criminal (while the Uchiha were the police force?) and ended up endangering Konoha for the time being.
