This is going to be extremely long so bear with me. This will be a somewhat in depth analysis of either sides' strengths and weaknesses.
Round 1: Luffy was trained probably since he could stand by his grandpa who was known as Garp the Fist. Remember, his grandpa used to fight the world's strongest man and almost kill him on a regular day to day basis, no further explanation needed. On a pure, raw physical power base, Natsu doesn't have as much feats as Luffy. Luffy can shatter steel with his bare hands (he shattered Jango's steel chakram with his jaw...), pushed two giant brick buildings apart in Water 7, and lifted a giant ball of gold in Skypeia. Both of them have an insane amount of will and endurance, but with Luffy, his fights drag on for several episodes and he has arguably survived a lot more life threatening shit than Natsu: survived Magellan's poison, defeated Hody Jones underwater (he's weak in water), Luffy vs Lucci check it out, etc. Furthermore, Luffy has been fighting based on raw physical strength more or less for most of the whole series, while Natsu can rely on physical strength and his magic. Based on all the evidence, Luffy would win in a raw fistfight, albeit with mid-level difficulty.
Round 2: MONKEY D. LUFFY:
STRENGTHS::
Gear 2 (insane boost in speed, range, and power; Natsu doesn't have speed like that and Luffy can basically snipe him with the speed of his attacks), Gear 3 (insane boost in power and area of influence) Note: Natsu destroyed a city with Atlas Flame's fire but Luffy shattered an island with Thor Axe against Shiki.
All THREE types of Haki: Kenbunshoku (basically a more powerful spidey-sense that allows him to predict his opponent's actions; Natsu wont be able to touch him unless he can exceed Luffy Gear 2 speed), Busoshoku (increases hardness and density of attacks, produces heat energy due to friction e.g. Red Hawk), Haoshoku (knocks out weak-willed people by glaring xD; doesnt work on Natsu sadly)
Fighting Genius and Creativity: (for the ones who follow one piece, Luffy doesn't have a set style he just "reacts" and fights based on instincts.) Ability to invent new techniques on the fly (fight with Crocodile) and fight with Enel. Natsu doesn't have the same level of adaptability that Luffy possesses.
Unpredictability: Natsu is REALLY straightforward. You have no idea what Luffy is about to do next cuz the way he thinks is too absurd to fathom.
On a side note: Luffy has more allies to back him up: Shanks, the original Gildarts Clive, the world's greatest transvestite Emporio Ivankov who coincidentally is Russian and looks like Frank-N-Furter, Trafalgar Law who looks like "Mystery" from Neil Strauss's The Game etc.
AND: Complete Immunity to blunt force trauma
WEAKNESSES:
-Can be wounded by sharp things, so maybe if Natsu shaped his fire into a spear...
-Weak to elemental abilities cuz after all fire burns. BUT, the tensile strength of rubber increases with the temperature up to a certain point. Luffy might realize this somehow and adapt (get hit just enough to become stronger than Natsu?)
-Motivated by extremely questionable things sometimes (Meat...)
NATSU DRAGNEEL:
STRENGTHS:
Fire Dragon Slayer Magic: Powerful magic that transforms his body physiology into that of a Dragon's. Uses it basically to the same extent as Ace. Augments physical attacks and can also be fired in various forms.
-Lightning Flame Dragon Mode: Comparable to Gear 2. Can only be used when Natsu is angry and depletes him much faster than Gear 2 depletes Luffy. Luffy is unaffected by lightning. Ups explosive and penetrative power, though Luffy can create explosive fists through Gear 2+Haki. Mostly useless against Luffy who has Kenbunshoku Haki and greater speed and reflexes.
-Can replenish energy and strength by eating external sources of fire (Luffy's Red Hawk might be useless...), though its unlikely there will be any fire unless Luffy pulls a Red Hawk
-Immunity to fire (Luffy's Red anything may be useless...)
DRAGON FORCE: Basically useless in this fight since he needs to eat magic...disappointing
-Crazy strength: Less physical power, but can easily be augmented by Dragon Slayer magic, although blunt force doesn't affect Luffy...
-Insane Battle Observation: Deciphered Sting and Rogue's behaviour and battle reflexes to near minute details. Comparable to Kenbunshoku Haki. BUT, may not work on Luffy who is very unpredictable.
WEAKNESSES:
-Motion Sickness
-Blunt force doesn't affect Luffy
-Very low adaptability compared to Luffy
-Stupid enough to try and eat Haki (even if Haki was energy, another "element" would greatly harm his body like when he ate Etherion.)
Result? Luffy wins with high level of difficulty. Natsu's physical attacks will have no effect on Luffy so he's gunna have to rely on his magic. There likely won't be any external fire in the match except say for maybe a Red Hawk, so Natsu cant replenish strength. Natsu's fire is heavily damaging for sure, but Luffy's survived far greater threats (got punched by Akainu's magma fist and survived with an epic scar) . Luffy has Kenbunshoku Haki (precognition) and Gear 2: spidey sense combined with extreme speed and power. Natsu wont be able to hit him let alone see him. Fairy Tail fights are too straightforward compared to One Piece fights and are A LOT shorter; Natsu has less time to adapt and learn compared to Luffy. Furthermore, Luffy is arguably a lot more "smart" compared to Natsu in combat as his somewhat questionable way of thinking can actually result in ingenious battle tactics (Gear 2, fight against Enel, fight against Lucci). In the end, it's an endurance battle: Either Luffy succumbs to Natsu's fire magic or Natsu runs out of magic power first. WHAT DO YOU GUYS THINK?
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