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Also, shouldn't speed be equalized? If not, blitzed
"randomly" - But anyways:
Askin's stats and regenerative powers are mostly vague. He did take hits from Island level characters and survived, but if we look stat-wise, couldn't he still be one-shot?
It's much safer to assume Doflamingo to take the initiative since Askin is very calm and quite confident in his powers (especially given how he sat there and underestimated characters like Yoruichi, her brother, and Oetsu Nimaiya), but if Askin can survive his strikes, he'd eventually become almost immune to his attacks.
But for him to deal poison damage to Doflamingo, Doflamingo would have to remain in range of his power, and Askin would have to consume his blood.
I find it hard for Askin to flat out beat Doflamingo, but Doflamingo's arrogance would more than likely make him lose his chance at killing Askin with his attacks, though it would take him a minute (according to his page). Gift Ball Deluxe is another factor unless Doflamingo can restrict Askin's movements and get out of range.
Projectiles hitting Doflamingo are low chance since he can use his threads to intercept them, or dodge them if he is not too close.
Unless Parasito is rendered completely useless (i think it would still be effective since it's not a "direct attack" that Askin can just tank), Doflamingo can POSSIBLY find a way to win.
Then again, if he can't harm Askin, he might find a way to just restrict his movements fully and thus BFR.
With BFR, Doflamingo should be capable of winning
No BFR, i'm leaning towards Askin. Even if Doflamingo decided to and successfully KILLED him at the start, Askin's Gift Ball deluxe would likely kill him (unless Doflamingo has a Black Knight active at the time) - Still, Askin's victory without BFR is more likely.
Askin is just too hax. Doflamingo has no real counter to the deathdealing. His best chance is to kill him before he gets affected by the deathdealing. And Askin wouldn't just sit their and let Doflamingo kill him.
Well, Askin adapted to an Island level attack in base. He would easily be able to do the same in Vollstandig leaving him immune to Doflamingo's Haki attacks.
He may have adapted to attacks from an island level character, but such attacks were not capable of instantly killing an opponent, and the island level character was pretty much toying with them.
In the case of Askin, Nimaiya only slashed his torso and then lopped his face off, which was not going to kill him quickly enough to prevent the Death-dealing from occurring. Sure, the blows were lethal and would've killed him, but over a small amount of time.
I'm leaning towards Doflamingo now that i'm looking back at Askin's fights given his care-free nature, and that Doflamingo CAN kill him in one blow and Askin needs to land his attacks to "poison" Doflamingo, which would be difficult to accomplish due to pre-cognition, enhanced vision, and his threads (as a shield) + personal agility.
I'm still confused towards some aspects of Askin's powers, though.
Didn't you also mention that Doflamingo's arrogant? Would he go for something that can kill Askin immediately without any knowledge of his powers? And which kind of attack does he have that can immediately kill Askin?
Doflamingo is arrogant, but he isn't at the level in which he'd simply let his opponent have the upper-hand. In his fights, he makes sure to avoid taking unnecessary damage whenever he can, and immediately cripples his opponent (against Law, Luffy [pre Gamma-Knife], and Oars Jr). Askin and Doflamingo are both combative experts and geniuses, but Askin is also quite arrogant with his power and his carefree nature has left him open to attacks.
Askin's Regenerationn is at a low level like Doflamingo's. Sure, he can heal from gashes to his body, but attacks that remove his limbs/head, leave a gaping hole in his torso or head, or leave his body in tatters would kill him.
Doflamingo's physical blows and thread attacks can already decapitate (as he removed Law's arm, Oar's leg, and [if not for Luffy] Kyro's head), his Awakened threads can shred and pierce Askin's body completely (poor Colosseum fighters).
Of course, he likely would not use his awakened threads to attack at the start if both are not knowledgeable of eachother, but in the case of knowledge or bloodlust (or both), Doflamingo definitely would try to end the fight quickly.
I could strongly argue that Doflamingo uses Everwhite to give himself the ground advantage, or his Kumonosugaki as an aerial advantage, and once he limits Askin's physical movements, land Parasito and use Goshikito/Athlito/Overhito to decapitate him in one blow.
Doflamingo is a fighter that lets his enemy attack first while he observes before actually throwing his own attacks, or uses tricks to break through their guard (Against Luffy in Round One, Kyros, Sanji, Oars Jr., and Atomos). He never fights head-on unless he is confident that he will prevail.
Unless Askin initiates the fight (Which I doubt since he is even more passive than Doflamingo), Doflamingo will initiate with Parasito or Black Knight and take care.
With no knowledge and this being a standard fight: Could go either way, but Doflamingo may prevail due to his tricks and potential to one-shot.
With knowledge: Doflamingo will instantly turn the entire battlefield into threads, which will force Askin to fight in the air, and Doflamingo can use Sora no Michi to eventually surround Askin, Kumonosugaki to restrict his aerial movements, and Flap/God thread to finish him in one blow.
With Bloodlust: Askin has a chance should Doflamingo briefly drop his guard, but Doflamingo still has pre-cognition and enhanced sight to boost his reaction speed. Doflamingo still has the potential to one-shot here and Askin, not knowing the details of Doffy's power, would likely fall prey to Parasito.
I know that Askin can one-shot Doflamingo with poison, but unless he can find a way to successfully break through Doflamingo's Awakening and pre-cognition, that is unlikely to happen, while Doflamingo can catch Askin with Parasito, Kumonosugaki, or Everwhite before throwing one of his own attacks
And Giftball deluxe will kill Doflamingo even if Askin dies, unless Doflamingo can get out of it with his powers, or Askin doesn't even use it.
I already know some of these from the Kakashi vs Doflamingo thread . Also, I'm not really interested in arguing but it could indeed go either way. If Doflamingo initiates the fight with an attack that would kill Askin, he could take it if Askin decides not to dodge or mitigate the attack somehow. But if he starts with an attack that can't kill from the onset, Askin would get immune to his attacks.
@Burning - Askin's power doesn't work immediately from what i've seen. Against Yoruichi and Niya, he took several blows before beginning to negate the damage.
I'd say Doflamingo has 2~4 chances to kill him with attacks that actually hit. I doubt (unless prior knowledge) Askin will anticipate Parasito, which will render him unable to move, and Doflamingo can kill him right there. And Askin's power (iirc) would become immune to attacks Doflamingo decides to initiate with (Threads, Haki, or Punches/kicks).
@Burning - i think his power works the same way, but if there is only a small alteration between a "poison" he has adapted to and another "poison" coming at him, he would have already adapted to it. Auswahlen Askin fought Yoruichi, but yes... in base.