Monkey D. Luffy is the main protagonist of Eiichiro Oda’s One Piece. His character arc began when he set out to sea with the aim of becoming the King of the Pirates. Having eaten the Gum-Gum Fruit, Luffy’s battle prowess has grown tremendously — and with more training, he’s become one of the strongest characters in One Piece. At the same time, Luffy has proven that he’s far from unbeatable.
In fact, there are actually many One Piece villains who beat Luffy once or even twice until the Straw Hat pirates eventually triumphed in the end. Furthermore, most One Piece story arcs involve at least one fight where Luffy either was forced to retreat or was outright defeated, and that adds suspense while also making the villain that much more impressive. Although Luffy has avenged his losses in several scenarios, there have also been characters that he would still have trouble fighting even now.
Updated on August 29, 2024, by Ajay Aravind: As a Shonen protagonist, Luffy is going to find some way to defeat his enemies, even if he’s defeated by them already. He becomes stronger than before by learning from his mistakes and refusing to give up. This feature, in addition to his powerful charisma, is certain to make him the King of the Pirates and one of the most influential individuals in his world. As such, we’ve updated this article with some more relevant information.
11 Higuma the Bear Threw Luffy Into the Ocean
Episode 4: “Luffy’s Past! Enter Red-Haired Shanks!”
Character |
Age |
Devil Fruit |
Japanese VA |
English VA |
---|---|---|---|---|
Higuma |
46 |
None |
Yukimasa Kishino |
Matt Hoverman |
Luffy’s first fight in One Piece was short, since Luffy was just a young boy and hadn’t started training with his new Gum-Gum powers yet. When Red-Haired Shanks visited Luffy’s hometown, a minor bandit lord named Higuma decided to bully everyone. Shanks took the high road by ignoring him at first, infuriating Luffy, who wanted him to fight back and avenge his spilled honor.
When Luffy later confronted this villain, the cowardly Higuma quickly defeated him and even tried to kill the boy. Fortunately, a sea monster known as the Lord of the Coast attacked and devoured Higuma. Once Luffy ended up in the water, however, Shanks arrived to rescue him, albeit at the cost of an arm. Higuma may be the first villain who defeated Luffy, but he didn’t have very long to boast about it.
10 Captain Smoker Cornered Luffy in Loguetown
One Piece Episode 53: “The Legend Has Started! Head For the Grand Line!”
Character |
Age |
Devil Fruit |
Japanese VA |
English VA |
---|---|---|---|---|
Smoker |
36 |
Smoke-Smoke Fruit |
Mahito Ohba |
Greg Dulcie |
Luffy’s first proper defeat in One Piece came at the hands of Captain (now Vice-Admiral) Smoker, who served as a Marine officer back during the Logue Town Arc. Being a Logia type made of smoke, it was effectively impossible for Luffy to beat Smoker with physical attacks. Although the Color of Arms Haki would have come in handy against Smoker, Luffy didn’t even know what Haki was at the time.
The battle between the two wrapped up quite quickly and ended in favor of Smoker. Ultimately, Luffy needed to be rescued and his father Monkey D. Dragon stepped in to save him instead. Luffy seized that opportunity to flee Loguetown — he and his crew set sail in a rainstorm for the Grand Line, leaving Smoker and Tashigi far behind. On the other hand, Smoker and Luffy have since developed a cautious alliance.
9 Luffy Foolishly Challenged Crocodile in the Alabasta Desert
Episode 111: “Dash For a Miracle! Alabasta Animal Land!”
Character |
Age |
Devil Fruit |
Japanese VA |
English VA |
---|---|---|---|---|
Crocodile |
46 |
Sand-Sand Fruit |
Ryuzaburo Otomo |
David Brimmer |
Luffy’s first big undertaking in the Grand Line came against one of the Seven Warlords of the Sea and the leader of Baroque Works, Crocodile. As a pirate, Crocodile was known to be ferocious, having sailed the seas of the New World in the past. As a Warlord of the Sea, however, Crocodile was leagues beyond Luffy’s initial power level. With his Sand-Sand Fruit powers, he was a tremendous enemy for Luffy, whom he considered to be nothing more than an annoying rookie.
Crocodile remains one of the few villains who defeated Luffy more than once, although the third battle ended resoundingly in Luffy’s favor. Nonetheless, Crocodile gave Luffy his first taste of what Grand Line was like, and Luffy nearly died in the process. Interestingly, Crocodile helped Luffy and his allies escape during the Impel Down Arc, proving that he harbors no ill will anymore.
8 Enel Temporarily Overpowered Luffy On Sky Island
Episode 184: “Luffy Falls! Enel’s Judgment and Nami’s Wish!”
Character |
Age |
Devil Fruit |
Japanese VA |
English VA |
---|---|---|---|---|
Enel |
39 |
Rumble-Rumble Fruit |
Toshiyuki Morikawa |
Wayne Grayson |
Enel thinks himself divine because of his rare Rumble-Rumble Fruit, which allows him to generate vast amounts of electrical energy. Luffy and the self-proclaimed Enel traded blows with each other during the Skypiea arc of One Piece when they met in the Upper Yard, the Land of God. Thanks to his rubber Devil Fruit, Luffy was able to withstand most of Enel’s attacks; however, the skill of the latter was still levels above him.
Luffy, inevitably, lost the first battle with Enel and had to fight him once again to beat him and save Skypiea. Even with the benefit of lightning immunity as a rubber warrior, Luffy was in for the fight of a lifetime. To secure victory, he had to tread carefully around a villain who had already defeated the Straw Hat Captain once before.
7 Luffy Only Rescued Robin Because Admiral Aokiji Let Them Go
Episode 228: “Duel Between Rubber and Ice! Luffy vs. Aokiji!”
Character |
Age |
Devil Fruit |
Japanese VA |
English VA |
---|---|---|---|---|
Aokiji/Kuzan |
49 |
Ice-Ice Fruit |
Takehito Koyasu |
Jason Douglas |
Prior to the Water 7 saga in One Piece, Luffy and the Straw Hat Pirates crossed paths with Kuzan, an Admiral of the Navy also known as Aokiji. With him being an Admiral, there could only be one possible winner for any battle between them. Luffy, even with help from Zoro and Sanji, stood absolutely no chance against someone who could literally turn the seas into solid ice.
Although the crew lost badly, Kuzan eventually spared them, a surprisingly tender moment from an otherwise solemn Marine. As a result of his loss, however, Luffy ended up getting stronger to make sure he had the power to protect those close to him. At the time, Kuzan was a benign antagonist whom Luffy had to carefully avoid, but in more recent One Piece arcs, Kuzan is a member of the Blackbeard Pirates, making him a deadly foe for both Luffy and the Navy.
6 Rob Lucci Defeated Luffy In the City of Water 7
Episode 246: “The Straw Hat Pirates Annihilated? The Menace of the Leopard Model!”
Character |
Age |
Devil Fruit |
Japanese VA |
English VA |
---|---|---|---|---|
Rob Lucci |
30 |
Cat-Cat Fruit, Model: Leopard |
Tomokazu Seki |
Jason Liebrecht |
Water 7 and Enies Lobby are two of One Piece‘s most exciting arcs, in no small part due to the surprise introduction of CP9. Luffy’s ultimate fight against Lucci is an iconic battle not only in One Piece but also in all anime and manga. Although their conflict at Enies Lobby is their most definitive battle, the two of them also clashed at Water 7, where Lucci ended up defeating him without much trouble.
Luffy attempted to attack Lucci with a kick, but the villain easily overpowered him with his Six Powers Technique and Cat-Cat Fruit: Model Leopard. On the way to Enies Lobby, however, Luffy developed Gear 2 and Gear 3 to keep up with CP9’s formidable power and rescue his shipmate Nico Robin from the Navy’s grasp. As always, Luffy learned quite a lot from his fight against Lucci, demonstrating as much when he defeats the villain.
5 Kuma And the Pacifistas Separated Luffy From His Crew On the Sabaody Archipelago
Episode 405: “Eliminated Friends – The Final Day of the Straw Hat Crew”
Character |
Age |
Devil Fruit |
Japanese VA |
English VA |
---|---|---|---|---|
Bartholomew Kuma |
47 |
Paw-Paw Fruit |
Hideyuki Hori |
Joel McDonald |
At Sabaody Archipelago, the entire Straw Hat crew was utterly defeated by a joint force of the Navy and one of the Warlords of the Sea, Bartholomew Kuma. Sentomaru and his squad of Pacifistas were also strong enough to completely overwhelm the crew, even if they had less diversity in their powers. Kizaru’s arrival made things exponentially difficult for Luffy and his crew, but it was Kuma who dealt the decisive blow.
To make things worse for Luffy, his entire crew was blown away by Kuma and the power of his Paw-Paw Fruit. Each of them was sent to a distant island, where they would spend the next two years training. To date, the battle against Kuma remains one of the biggest losses that the Straw Hat captain has ever suffered, although the former Warlord’s role in One Piece is beginning to change.
4 Magellan Poisoned Luffy In Impel Down
Episode 436: “The Showdown Has Come! Luffy’s Desperate Last Attack!”
Character |
Age |
Devil Fruit |
Japanese VA |
English VA |
---|---|---|---|---|
Magellan |
47 |
Venom-Venom Fruit |
Mitsuaki Hoshino |
Jeremy Inman |
In an attempt to rescue his foster brother Ace, Luffy broke into the greatest known prison in the world of One Piece, Impel Down. He reached that prison’s hellish fourth floor by the time Warden Magellan himself caught up to Luffy, and they fought a short but vicious battle there. Luffy had a few allies at the time, such as Buggy and Mr. 3, but they were in no position to support Luffy against the mighty warden.
Luffy stood little chance against Magellan’s Venom-Venom Fruit, which soon had him writhing in agony, dying from deadly toxins. Magellan showed a little mercy after he saw Luffy defeated, and sent Luffy to Level 5 rather than just kill him outright, giving Mr. 2 and Ivankov one last chance to save the Straw Hat hero’s life. Although it took a great deal of time and patience before Luffy would wake up again, he has since become even more immune to poisons than before.
3 Luffy Bit Off More Than He Could Chew At Marineford
Episode 466—Episode 489
Character |
Age |
Devil Fruit |
Japanese VA |
English VA |
---|---|---|---|---|
Monkey D. Luffy |
19 |
Human-Human Fruit, Model: Nika |
Mayumi Tanaka |
Colleen Clinkenbeard |
The Marineford Arc is arguably the most explosive storyline in One Piece. There are multiple simultaneous battles taking place all over the eponymous island, pitting the most dangerous pirates in the world against the strongest Marines. Luffy’s arrival will no doubt be remembered among the greatest anime scenes of all time — a young boy facing off against three Admirals armed with nothing more than a log.
He also properly used his Conqueror’s Haki for the first time at Marineford, knocking out hundreds of enemy combatants and earning the Admirals’ grudging admiration. That said, Luffy ultimately failed to achieve his goal. He couldn’t save Ace because his big brother was too busy saving him from Akainu’s fatal attack. Ace’s sacrifice left Luffy in a catatonic state, ending his role in the Summit War. Fans can’t wait to see Luffy take revenge against Akainu.
2 Luffy Fought Katakuri in the Tea House on Totto Land
Episode 833: “Returning the Sake Cup! The Manly Jinbe Pays His Debt!”
Character |
Age |
Devil Fruit |
Japanese VA |
English VA |
---|---|---|---|---|
Charlotte Katakuri |
48 |
Mochi-Mochi Fruit |
Tomokazu Sugita |
Jonah Scott |
Just like other major battles, Luffy fought the antivillainous pirate Charlotte Katakuri a couple of times before he actually managed to get on his level and defeat him in combat. The two clashed at the Tea Party first, where Luffy needed saving from Jinbe. Later, Luffy and Katakuri fought again in the Mirro-World created by Charlotte Brûlée.
The Sweet Commander proved his superiority over the Straw Hat captain yet another time, forcing him to abandon the fight until his Haki returned. In the final battle, however, Luffy triumphed with the superior use of Color of Observation Haki and a new technique called Snakeman, though it was still a close fight. That final fight was a battle of true equals, with Luffy and Katakuri both being melee fighters with Haki and stretchy Devil Fruit powers.
1 Luffy Miserably Loses His First Fight With Kaido In Wano
Episode 915: “Destructive! On Shot, One Kill – Thunder Bagua!”
Character |
Age |
Devil Fruit |
Japanese VA |
English VA |
---|---|---|---|---|
Kaido |
59 |
Fish-Fish Fruit, Model: Azure Dragon |
Tessho Genda |
David Sobolov |
Monkey D. Luffy went head-to-head against one of the Four Emperors of the Sea, Kaido, in the Wano Country arc of One Piece. Although the plan was to take Kaido down at Onigashima, Luffy first engaged the Emperor in Kuri, hitting him with everything that he had at once. Kaido took the fight lightly and was extremely intoxicated at the time, and it initially seemed that Luffy had the advantage.
However, Kaido took the full brunt of the attacks without suffering any real damage. He subsequently transformed back into his human appearance and decided to take Luffy seriously. With just one swing of his legendary Thunder Bagua, Kaido knocked Luffy out and defeated him with casual ease. This allowed Kaido to join the ranks of One Piece villains who beat Luffy before finally facing his own defeat later on.
Luffy Is Likely To Lose At Least A Couple More Battles Before Finding The One Piece
With the Final Saga in full swing, Luffy and his crew are consistently fighting their way through the Egghead Incident in the manga. The Straw Hat captain has already secured yet another win against Rob Lucci, although they both fought with Awakened Devil Fruits this time. However, things are heating up for the entire world, as quite a few individuals are interested in finding the One Piece. This includes powerhouses like Shanks, Blackbeard, and the Cross Guild, although Kaido and Big Mom also made the same plan before their disappearance/death.
Given how effortlessly Shanks eviscerated Eustass Kid and his entire ship, however, it seems that even a fully functioning Gear 5 won’t be enough for Luffy to defeat his idol. Furthermore, the Navy, Fleet Admiral Akainu, the Five Elders, and the mysterious Imu also have a stake in preventing the discovery of the One Piece. In order to avenge Ace, Luffy might have to battle Akainu and Blackbeard, both of whom are overwhelmingly powerful. In any case, it won’t be fun to see Luffy cheerfully win his way to Laugh Tale, so Oda probably has a few losses for him planned.