When Naruto is being discussed online it is most commonly discussed from the reader's perspective. Speculation based on that is fruitless. To allow for a productive (heh) discussion the subject has to be viewed from the perspective of the writer, not the reader. The question is not "What would Sasuke do in situation X?", but rather "What would Kishimoto have Sasuke do in situation X". As an example i will take the first major fight from after the timeskip. Deidara vs Gaara. At the end of one of the chapters, Deidara clearly looks outmatched. He just got caught by Gaara's Sand Prison technique. This spawned lots of possible predictions about the next chapter, many of which involving Deidara getting pwned. Once these theories where proven wrong with the defeat of Gaara, people started speculating (not necessary the same "people" as in the previous predictions) that Gaara would go Shukaku on Deidara soon because he was knocked unconscious ("Gaara is just fooling them", etc. etc.). This was also wrong. Now this leads up to the Itachi vs team Kakashi and Kisame vs team Gai battles. People thought that Kisame actually WAS killed there (strange cliffhanger ending after the Asakujaku taijutsu tech). Of course, it makes sense if you don't really think about it. But finally it was revealed that Kisame was not killed, and neither was Itachi. Surprising, eh? After this the Sasori vs Sakura & Chiyo battle starts. Sasori was killed. Deidara also at this time fought Naruto and Kakashi and lost. He did not die, however. All of this could've been seen coming if you think about it. WHY would Deidara lose to Gaara? What purpose would it serve to introduce a new villain only to have him LOSE in the first fight he's involved with against a non-main character? Having him getting killed by Shukaku right after Gaara's defeat was slightly more believable from a storyline perspective, but still... And it was obvious that Itachi wasn't going to get killed by Kakashi and Naruto in the following fight. He has too strong connections to Sasuke to be killed by them. It would actually be kindof logical to have Kisame killed by Gai, but the fight was all too short and not "epic" enough for a final fight so you could see he wasn't going to get killed. Sasori's demise was getting more and more obvious the longer the fight went on. From the beginning i thought he was going to get out of it alive, but the more powerful moves he showed, the less likely he was to get out of it alive. Deidara was obviously not going to be defeated without causing atleast some environmental destruction. He wasn't even fully armed during his fight. To conclude this: The probability of someone winning a fight cannot be determined by comparing the strength of the fighters. You have to see patterns in the writing style of the writer. You have to try to think like he does. Kishimoto has showed himself unwilling to kill any main character (damn you Chouji). Therefore it was obvious that Kankurou would not die from the poison and Sakura wouldn't die from the sword wound by Sasori. Now... Why did i post this in the first place, you ask? Well, someone had a theory about Shino's dad being the Akatsuki leader. This is sortof a response to that one. I think you can figure out the connection yourself.