Arc
Episode No.
Episode Name

Wano Country
1076
“The World That Luffy Wants!”

Luffy lost badly to Kaido the first time they clashed in Wano, but as manga fans know, Luffy prevailed in the end against the strongest living creature in the world. Not even Luffy’s best Gear 4 moves could take down Kaido. At the last moment, however, Luffy Awakened his Gum-Gum Fruit and manifested the power of Nika, the Warrior of Liberation.

Now Luffy wields the incredible power of Gear 5, transforming him into a goofy but unstoppable warrior with cartoon physics. In this overwhelming form, Luffy secured his final victory over Wano’s greatest tyrant, leaving Kaido to fall into an abyss. This further allowed him to replace Kaido as one of the Four Emperors. Luffy also got a massive bounty to match his impressive victory, showing just how far he had come since the early days.

Luffy’s Humiliating Defeats Helped Him Grow Stronger

Admiral Aokiji Freezes Monkey D. Luffy and Nico Robin Solid

Arc
Episode No.
Episode Name

Long Ring Long Land
228
“Rubber and Ice One-On-One Fight! Luffy vs. Aokiji!”

Although One Piece has over 1,000 episodes it’s a richly rewarding experience and it’s never been a better time to begin a voyage with the Straw Hats.

Luffy and his friends did well against the tricky Foxy the Silver Fox during the filler-style Long Ring Long Land arc, but those warm, fuzzy feelings of victory didn’t last long. Of all the people for the Straw Hats to encounter, the mighty Admiral Aokiji arrived on the island where they had taken shelter. This was the first time viewers had seen an Admiral in battle, and Aokiji proceeded to teach the Straw Hats a brutal lesson about the Navy’s true power.

The combined Straw Hats stood no chance against the Admiral, and even the defiant Luffy got frozen solid with frightening ease. Fortunately, Aokiji was in a forgiving mood and let the Straw Hats go, partially because they had recently taken the villainous Crocodile and his Baroque Works out of the political equation. In any other situation, Luffy and his pals would have been hauled straight to Impel Down in shackles.

Bartholomew Kuma Effortlessly Defeated Luffy During Their Second Encounter

Arc
Episode No.
Episode Name

Sabaody Archipelago
405
“Disappearing Crew – The Final Day of the Straw Hat Crew”

Bartholomew Kuma, in both his show-offs against the Straw Hats, demolished them with his powerful Paw-Paw Fruit’s abilities. During their first clash after the events of the Thriller Bark arc, for example, the Straw Hats were in no shape to resist Kuma because they were injured and exhausted from fighting Gecko Moria. Luffy was already unconscious when Kuma arrived on Thriller Bark, so Zoro decided to take on the responsibility.

Not long after that, Luffy and his crew faced Bartholomew Kuma again at Sabaody Archipelago, and Round 2 didn’t go any better than the first. This fight made clear the difference between Luffy and Kuma, which is why the Straw Hat ordered his crew to retreat for the first time ever. In fact, Kuma was the one who used the Paw-Paw Fruit to fling the Straw Hats all over the world, setting them up to each train alone until they reunited two years later.

Magellan Was Far Stronger And Tougher Than Luffy Could Handle

Arc
Episode No.
Episode Name

Impel Down
436
“The Fight Finished! Luffy’s Final Life Risking Attack”

Monkey Luffy, for once, wanted to use stealth to get the job done and rescue his foster brother Ace from the dreaded undersea prison Impel Down. As expected, fighting broke out and Luffy’s cover was blown. Luffy started fighting his way through the prison’s hellish levels, defeating numerous opponents along the way. By level 4, Luffy finally met his match against the warden himself, Magellan.

Magellan’s Venom-Venom Fruit allowed him to use deadly poisons in all kinds of ways, and Luffy had no counter to that power. Luffy knowingly sacrificed both arms to punch Magellan with all his might, but it was all in vain. Magellan’s own counter-attack soon had Luffy dying on level 4’s floor. It took a ton of effort from Ivankov and Bon Kurei to ensure Luffy’s survival. On a positive note, however, Luffy has since developed an impressive level of resistance against a wide range of toxins.

Kaido Casually Knocked Luffy Out During Their First Battle

Arc
Episode No.
Episode Name

Wano Country
915
“Destructive! One Shot, One Kill – Raimei Hakke!”

Early in the Wano saga, Luffy and his friends realized that the reclusive nation of Wano was under the thumb of two brutal tyrants. Shogun Kurozumi Orochi and the mighty Kaido, one of the Four Emperors, had been governing Wano for two decades when the Straw Hats reached the island. Luffy soon got a taste of what Kaido was capable of, and it ended badly.

Even when Kaido was intoxicated and held back, he was more than a match for Luffy, and no Gear-based attack could put Kaido down. Even techniques like Grizzly Magnum, Elephant Gatling, and Kong Organ had zero effect on the formidable Emperor. When Kaido decided that enough was enough, he casually whacked Luffy unconscious with his iconic Thunder Bagua ability. Luffy would spend the next few days incarcerated in Udon.

Luffy Lost Ace Despite Displaying His Overwhelming Courage

Arc
Episode Nos.
Episode Name

Marineford
483
“Looking for the Answer – Fire Fist Ace Dies on the Battlefield”

The Marineford arc still stands as one of One Piece‘s best, a massive all-out battle that featured some of the strongest characters in the story. Luffy wasn’t trying to win any wars, though; he only wanted to rescue Ace from execution. As such, he waded his way through an apocalyptic battlefield of pirates and Marines, even releasing his Conqueror’s Haki without realizing it.

Tragically, Luffy was too late. He fought hard, but he was no match for Admiral Akainu’s lava punches — and for that matter, neither was Ace. To Luffy’s horror, Ace had to take the blow for him and died of his wounds, leaving a grief-stricken Luffy who had no idea what to do. He essentially checked out of the situation, forcing his allies to intervene. Physically and emotionally, Luffy suffered a horrific defeat, but at least Trafalgar D. Water Law was around to bail him out safely.