Fantastische Hure said:
Doesn't Kabuto have that regeneration jutsu? That could help him.
It takes him a while to fully heal though. Kakashi wouldn't waste the opportunity of the type of opening that would provide.
Kabuto mostly lost because of PIS. On-top of that he got hit by a technique that only Jiraiya and the fourth could ever perform. Something that was thought impossible for him to learn in that amount of time, so it caught him off-guard too to an extent. Could Kakashi take it head-on?
I'd agree to the off-guard part, as well as probably the PIS part when considering Sharingan Sasuke in the following arc could stalemate it with the Chidori. Still, I'd say you could also make the argument of Kabuto being a class cannon. He isn't that well known for fighting in a direct, melee confrontation (especially with him putting up the facade of being a failure Genin for so long) and quite reliant on his medical jutsu, compared to a veteran of countless battles and constant equal to a taijutsu expert like Guy as Kakashi is.