With Kaito, it all depends on how he decides to play the game with his territory. And he never says all the rules completely anyway. So without the ability to overpower his territory, (which I don't know if that's possible for any normal person without some kind of reality warping ability) or the power to mindrape him he should hardly loose unless he plays a game like he did against Kurama. or CIS gets involved. The fact you can't have the same letters in order than spell out a certain word is a big advantage for Kaito also if you have nobody to find it out for you like Kurama did.
Originally posted by Kentonah, i meant wits in terms of developing a fight strategy.
In a battle of wits, Light, Near, L, Conan Edogawa. They could probably all outwit Shikamaru.
If you give everyone you mentioned, along with Shikamaru, time to develop a plan and arm them all with detailed information on what their opponent is capable of.... Shikamaru, ftw!