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What if the fight had been allowed to continue? Kurenai left to take Kakashi to safety but Asuma and Gai stayed back to handle Itachi and Kisame. Who ends up taking it?

Akatsuki pair would win. Dunno if they can do it before the Anbu show up. Probably.

Asuma holds back Gai too much.

Definitely the Akatsuki. Gai and Asuma can put up some fight, but they're both outmatched.

We don't know if Gai can do Afternoon Tiger yet, for that matter.

If Asuma flees and Gai sacrifices himself to open all the gates, Itach and Kisame lose every time.

Itachis pretty good... guys a major threat having experience with kakashi... feel bad for asuma

Asuma's the weakest one here. He goes down easily to Kisame. 6 Gate+ gai is the real threat here, and since he' going to be fighting on the water and not look into Itachi's eyes, Itachi can't cast Tsukuyomi on him. Itachi either uses Ephemeral or Amaterasu before Guy can release the gates (which itachi can easily see coming) or a Susanoo to make sure that even if he releases to the gates, gai's attacks will be null.

Originally posted by NemeBro
Asuma holds back Gai too much.