Ranking Every One Piece Pirate That Defeated Monkey D. Luffy

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This list contains spoilers for One Piece.

Monkey D. Luffy is easily one of the most powerful characters in the anime and manga series One Piece. He’s a pirate who has consistently grown stronger, and is now recognized as one of the Four Emperors. Despite his current incredible power, Luffy hasn’t always been victorious and has faced defeats in the past.

During his adventures as a pirate, Luffy has faced several powerful opponents who managed to defeat him in battle. While these pirates are uncommon and possess unique strengths, they’ve all left their mark on the Straw Hat crew.

Sir Crocodile

Crocodile stands out as one of the very first pirates to truly defeat Luffy. He was Luffy’s first real challenge in the Grand Line, and he proved to be a formidable opponent. Before facing Crocodile, Luffy had easily overcome all of his enemies. Crocodile changed that, defeating Luffy and leaving him near death not once, but twice. Their first battle in the desert clearly demonstrated the significant difference in their abilities.

Crocodile easily beat Luffy twice in a row, first within a set time limit, and then by draining all the moisture from his body. Luffy only survived those encounters by chance and eventually won their third fight. However, Crocodile was the clear victor in the first two rounds.

Bartholomew Kuma

I remember watching the Straw Hat Pirates get completely broken up in the Sabaody Archipelago. Bartholomew Kuma was the one who did most of the damage – he was unbelievably strong, easily taking on the entire crew. He used his Devil Fruit power, the Nikyu Nikyu no Mi, to scatter them all. It seemed like he was trying to help, but it was still a devastating defeat for the Straw Hats, and it clearly left a lasting impact on them. They were really shaken up for a long time after that.

Big Mom’s Enraged Army

During the Whole Cake Island story arc in One Piece, Luffy faced an overwhelming defeat. After Charlotte Cracker was beaten, Big Mom unleashed a massive army of powerful pirates, and they showed Luffy no quarter. It was a decidedly unfair fight, as Luffy was forced to battle 10,000 pirates single-handedly – each one a dangerous opponent with a substantial bounty.

Luffy was too tired to defeat his enemies by himself, but he fought bravely anyway. Ultimately, he was overwhelmed and imprisoned in the Book Prison by Mont d’Or.

Big Mom

During the Whole Cake Island arc of One Piece, Luffy and Big Mom never truly battled. Their encounter was more of a brief clash, which was enough to demonstrate Big Mom’s superior strength. Luffy tried to attack her directly, but she easily blocked his strikes and quickly overpowered him.

Luffy ran out of energy and needed Sanji to carry him. While not a complete defeat, it was definitely a low point for the Straw Hat captain – he was completely powerless. Sanji saved his life, and it’s a shame Luffy and Big Mom never had a full-on fight, as fans were really hoping to see that. Hopefully, if Big Mom survives, they’ll get a chance to battle properly in the future.

Kaido

Without a doubt, Kaido is the pirate who dealt Luffy his most crushing defeats in One Piece. Their first fight in Kuri was a clear victory for Kaido, with Luffy completely overwhelmed and defeated by a single blow. Even after Luffy gained significant strength, he lost to Kaido two more times on the rooftop of Onigashima, being knocked unconscious in both battles.

Man, seeing Luffy finally beat Kaido was incredible, but it wasn’t easy! Kaido handed Luffy more defeats than anyone else in the whole series, seriously. The first time, Kaido just blew him away with Raimei Hakke. Then, he knocked Luffy out cold with Raganaraku. After that, Luffy got sent flying off the roof of Onigashima and was luckily saved by the Heart Pirates. It got even worse though – Luffy lost again, and this time he actually died! But that’s when things really changed. Somehow, falling actually made him stronger, and he used that newfound power to take down the Yonko. What a fight!

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2025-11-16 05:34