Sai was a former member of Danzo Shimura's Foundation and Sasuke's replacement for Team Seven in the Naruto universe. Despite his awkward mannerisms and clumsy social skills, he was a powerful shinobi on account of his ink-based jutsu and formidable melee prowess.
Whatever he drew would spring to life, possessing all of the qualities designed in the original picture. Nonetheless, this technique was not without flaw. Through matching him against an expansive roster of enemies, we can discern the versatility of Sai's abilities and how skillful in a fight he actually is.
10 WOULD LOSE TO: Choji Can Crush Sai's Ink Creations & Roll Him Flat
Choji showed little effort in crushing Sai's ink creations during the ninja's first encounter with Naruto Uzumaki. Only a partially expanded fist was necessary not only to belay his adversary's tiger (Sai's most prolific creation) but also to eradicate it entirely.
Though Sai's melee skills are commendable (capable of fighting Omoi and Karui simultaneously, two talented ninja from the Cloud village), it cannot compare to Choji's super expanded form. Alternatively, the human boulder could crush the soft-spoken shinobi flat along with any creations he might summon to defend himself.
9 COULD BEAT: Sai Has Many Advantages Over Tayuya, Including Mobility & Diversity Of Minions
Tayuya was a member of the Sound Four who could summon three ogres by playing a flute. Though they are strong enough to obliterate the boughs of trees, the kunoichi can't invoke their aid if she is not actively playing her instrument.
Considering how Sai can summon giants more powerful than hers at a moment's notice and does not need to actively manipulate them in order to fight, he is at a tremendous advantage. The Konoha shinobi's odds are even more favorable when considering he isn't limited to only three minions.
8 WOULD LOSE TO: Zabuza Is A Deadly Mercenary Whose Water Dragon Is Nearly Unstoppable
Zabuza's water-based jutsu (particularly his dragon, barrier, and clones) would all prove natural foils to Sai's ink creations since they can effectively wash them away. This would force the two into a melee altercation, one that the mercenary is better equipped to win.
Not only does Zabuza have vastly greater combat skill (capable of killing an army of men without using his arms and nearly defeating Kakashi in a taijutsu fight), but his Executioner's Blade also has far greater weight and reach than Sai's comparatively diminutive weapon.
7 COULD BEAT: Sai Can Keep Out Of Range From Shikamaru's Shadow Possession As His Creatures Attack
Shikamaru was nearly able to capture Sai with his shadow possession during their first encounter in the Leaf. Despite already dealing with both Choji and Naruto, Sai managed to get out of the way, illustrating adept reflexes and skill.
He can also draw and animate his ink creations in seconds, assailing Shikamaru with a host of monsters in the midst of dodging his attacks. This would force the tactician to retract his ability and brace himself - all while Sai creates more foes to do his bidding.
6 WOULD LOSE TO: Jugo Is A Juggernaut Who Could Shrug Off Sai's Attacks
Jugo's enhanced body and strength would prevent most of Sai's creations from harming him. His tigers' fangs would be entirely impotent, and his snakes would fail to immobilize the juggernaut at all.
Sai's giants would be the only utility with a chance at cracking Jugo's carapace, even if they're nowhere near as strong as the Fourth Raikage (whose punch sent the man flying during the Five Kage summit). Jugo could throw projectiles at the shinobi's ink bird to send him plummeting out of the sky.
5 COULD BEAT: Sai Could Continuously Overwhelm Hidan & Ensure He Never Has A Chance To Draw Blood
Hidan's jutsu is only effective if he can draw the blood of his target, and he is limited entirely to melee combat. Since Sai has displayed incredible mobility (able to dodge dozens of Deidara's explosions and avoid the brutal lunges of Gozu), it follows that he should be able to remain well out of the Akatsuki member's reach. This is especially true if he fights from the safety of a winged creation.
Sai would only need to send down ink tigers and ogres to slowly but surely wear Hidan out and break his immortal body.
4 WOULD LOSE TO: Sasuke Could Obliterate Sai Using The Susanoo
Sasuke has dozens of options for defeating Sai. He could use his Rinnegan for spatial displacement (allowing him to appear above his enemy's ink bird and deliver a punishing Chidori) or simply remain within the confines of a massive Susanoo and cleave down his Team 7 replacement.
Though Sai's ink ogres are mighty enough to create small craters with their fists, they wouldn't stand a chance of sundering Sasuke's impervious defenses.
3 COULD BEAT: Torune's Poison-Oriented Fighting Style Would Be Worthless Against Sai's Ink
Torune was an agent of the Foundation who could kill enemies in a single touch since his body is secreted poison. However, Sai is likely privy to the nature of his techniques since they are in close proximity with one another under Danzo Shimura.
Similarly to Hidan, Sai's success against Torune is guaranteed so long as he remains out of his reach and atop his ink bird. By sending a relentless onslaught of ogres and lions against the villain, he'd eventually wear him out and take his life.
2 WOULD LOSE TO: Danzo Has Measures In Place To Defeat Any Rogue Foundation Agent
Danzo ensured absolute loyalty from his subordinates through a number of treacherous and creative means. Considering that he placed a seal on Sai's tongue to prevent him from sharing Root's secrets, it follows that he'd have other countermeasures ready if his former student attempts to turn against him.
Even if he didn't have any precautionary tactic, the Baki (Danzo's elephant summon) would be capable of suctioning Sai from his mount, where a paralysis rune would await him. Shimura would then seize the opportunity to create a wind blade and cut the artistic shinobi down.
1 COULD BEAT: Zaku's Attacks Are Too Straightforward To Be Threatening
Zaku was capable of attacking opponents through concentrated tubes of piercing sound in his palms. They were devastating enough to cause menacing ripples throughout a small forest clearing and intimidate Shikamaru's team into remaining cowed behind the bushes.
Though the Sound ninja's technique would make flying inadvisable, Sai could dodge his enemy's blasts with the same reflexes he used against Deidara's explosions and Shikamaru's shadow possession. Once the distance has been closed, the hero could dispatch Zaku with a kunai.