Itachi and Kakashi vs. Pein

This is assuming that Itachi does not have a terminal illness.
Kakashi can use mangekyo sharingan (this is all in shippuden btw)
Pein has all six paths.

Here are their jutsus they can use:

Itachi:

Amaterasu
Clone Great Explosion
Crow Clone Technique
Demonic Illusion: Burning Paper Body
Demonic Illusion: Mirror Heaven and Earth Change
Demonic Illusion: Shackling Stakes
Ephemeral
Fire Release: Dragon Fire Technique
Fire Release: Great Fireball Technique
Fire Release: Phoenix Immortal Fire Technique
Scattering One Thousand Crows Technique
Shadow Clone Technique
Susanoo
Transcription Seal: Amaterasu
Tsukuyomi
Water Clone Technique
Water Release: Water Fang Bullet

Kakashi:

Jutsu/Weapon
Chidori
Demonic Illusion: Hell Viewing Technique
Earth Release: Earth Style Wall
Earth Release: Inner Decapitation Technique
Earth Release: Underground Projection Fish Technique
Eight Gates
Evil Sealing Method
Fire Release: Great Fireball Technique (Anime only)
Front Lotus (Anime only)
Hidden Mist Technique (Anime only)
Kamui
Lightning Blade
Lightning Hound
Lightning Release Shadow Clone
Multiple Shadow Clone Technique
One Thousand Years of Death
Rasengan
Shadow of the Dancing Leaf (Anime only)
Silent Homicide Technique
Summoning Technique (Dogs)
Summoning Technique: Earth Release: Tracking Fang Technique
Tornado of Water (Anime only)
Water Clone Technique
Water Release: Grand Waterfall Technique
Water Release: Water Dragon Projectile Technique
Water Release: Water Encampment Wall
Water Release: Water Shark Missile Technique
White Light Chakra Sabre

Pein:

Banshō Ten'in
Chakra Disruption Blades
Chibaku Tensei
Fierce Raining at Will
Five Seals Barrier
Flaming Arrow of Amazing Ability
Illusionary Dragon Nine Consuming Seals
King of Hell
Magic Lantern Body Technique
Mirrored Sudden Attacker
Sealing Technique Absorption Seal
Shapeshifting Technique
Shinra Tensei
Six Paths of Pain
Soul Removal (Unnamed)
Summoning Technique (Multiple)
Wind Release: Violent Wind Palm

who wins?

Pein just stomps this one.

Itachi and Kakashi own pain.

2 Genius with a high arsenal of jutsu against 6 bodies controlled by 1 person who just has an arsenal of jutsu.

Kakashi Kamuis 3 of the bodies. Itachi uses amaterasu on another 2. and susano'o the rest

Pein stomps hard.

Originally posted by Csdabest
Itachi and Kakashi own pain.

2 Genius with a high arsenal of jutsu against 6 bodies controlled by 1 person who just has an arsenal of jutsu.

Kakashi Kamuis 3 of the bodies. Itachi uses amaterasu on another 2. and susano'o the rest

Originally posted by King Kandy
Kakashi takes out three bodies when two easily owned him? WTF?

Two didnt easily owned him. He was in control the whole fight. and disable one of the bodies before Chouza came into the picture. Pain had no idea where kakashi was and most likely kakashi could have cougth deva off guard if reinforcements didnt come in. So yes. And kakashi didnt use kamui on 3 of those bodies. Like he could have. Why because its takes to much chakra and there were mroe fighting to be done.

Given the situation they were in. If reinforcements didnt come. Deva would have most likely had been killed. And Asura destroyed throroughly.

Originally posted by Csdabest
Two didnt easily owned him. He was in control the whole fight. and disable one of the bodies before Chouza came into the picture. Pain had no idea where kakashi was and most likely kakashi could have cougth deva off guard if reinforcements didnt come in. So yes. And kakashi didnt use kamui on 3 of those bodies. Like he could have. Why because its takes to much chakra and there were mroe fighting to be done.

Given the situation they were in. If reinforcements didnt come. Deva would have most likely had been killed. And Asura destroyed throroughly.

Anyway, Pain for the win. One-shots both with Shinra Tensei.

Itachi solo..

Originally posted by Slaanesh
Itachi solo..

Originally posted by ThunderGodEneru
Keep thinking that.

Anyway, Pain for the win. One-shots both with Shinra Tensei.

When has Shinra Tensei killed anyone? at best it broken Shikamaru leg.

http://www.onemanga.com/Naruto/422/15/
one body down and deva is paralyzed

http://www.onemanga.com/Naruto/422/17/
Kakashi was prepared for it and as you see his hand is filled with raikiri. He could have easily struck down pain while off guard. nothing would have stopped him. He even thanks them cuz now he can save chakra. Hell he could have easily kamuied Pain head off at that time.

So no. Kakashi didnt get owned. Chouji and Chouza screwed things up

If he'd Raikirid God Realm could have just repelled it.

5 second rule. Pain just used bansho tenin needing another 5 second recharge. That and he had no idea where kakashi was. So how is he going to repelle something he doesnt see coming?

Originally posted by Csdabest
5 second rule. Pain just used bansho tenin needing another 5 second recharge. That and he had no idea where kakashi was. So how is he going to repelle something he doesnt see coming?

Ah but you dont need to know it in order for you to take advantage. Pain would have been screwed.

Also pain has shown to do it in just 1 direction. And pain wouldnt know when to use Shinra tensei because he has no idea where kakashi is. Kakashi aready cought him off guard once when he tried to kill Iruka. There is nothing stomping him from doing the same. But instead oc catching a sword. Kakashi rams a raikiri through the back of his head.

Originally posted by King Kandy
O RLY?!

Originally posted by Csdabest
Ah but you dont need to know it in order for you to take advantage. Pain would have been screwed.

Also pain has shown to do it in just 1 direction. And pain wouldnt know when to use Shinra tensei because he has no idea where kakashi is. Kakashi aready cought him off guard once when he tried to kill Iruka. There is nothing stomping him from doing the same. But instead oc catching a sword. Kakashi rams a raikiri through the back of his head.

One direction? http://www.onemanga.com/Naruto/442/13/

Originally posted by Kento
One direction? http://www.onemanga.com/Naruto/442/13/

Originally posted by Csdabest
Also pain has shown to do it in just 1 direction.

Originally posted by Csdabest
When has Shinra Tensei killed anyone? at best it broken Shikamaru leg.

http://www.onemanga.com/Naruto/422/15/
one body down and deva is paralyzed

http://www.onemanga.com/Naruto/422/17/
Kakashi was prepared for it and as you see his hand is filled with raikiri. He could have easily struck down pain while off guard. nothing would have stopped him. He even thanks them cuz now he can save chakra. Hell he could have easily kamuied Pain head off at that time.

So no. Kakashi didnt get owned. Chouji and Chouza screwed things up

http://www.onemanga.com/Naruto/434/10/

Are you going to sit here and tell me Itachi and Kakashi are more durable than them?

And Deva Pain wasn't paralyzed, Kakashi could Rakiri Asura Pain all he wants, it would matter not when Shinra could then kill him.

Factual statement: Even with the help of others, Kakashi lost to two of Pain's bodies, one of the bodies was destroyed in a cheap-shot. And you think Kakashi can fight all of Pain's bodies at once? Idiotic.

Originally posted by ThunderGodEneru
It shattered the bones of Gamabunta and the other two giant toads in one attack.

http://www.onemanga.com/Naruto/434/10/

Are you going to sit here and tell me Itachi and Kakashi are more durable than them?

And Deva Pain wasn't paralyzed, Kakashi could Rakiri Asura Pain all he wants, it would matter not when Shinra could then kill him.

Factual statement: Even with the help of others, Kakashi lost to two of Pain's bodies, one of the bodies was destroyed in a cheap-shot. And you think Kakashi can fight all of Pain's bodies at once? Idiotic.

You must look at what they were slung into. They all hit something hard and crashed in mountains. Shinra tensei by itself does nothing but push people back. All those who didnt fly back hard into something got out with minimal damage. Kakashi was slung into a building and was in rubble and still was fine. Not only that but Kakashi knows Pain secret of his jutsu and what is capable of beating it. Wall climb. If he performs his chou shinra kakashi and itachi will most likely survive. And The main pain would be out for like 10 mins. And Pain has no defense against Susano'o or Kamui. Yet counters for Pain are availble.