Summary
Monkey D. Luffy is the protagonist of Eiichiro Oda’sOne Pieceseries. Intending to become the Pirate King, Luffy set out to sea in an era where pirates are on the rise. To attain this title, Luffy has had to become stronger with every obstacle that he’s faced.
Over the years, Monkey D. Luffy has gained several new powers as he crushed his enemies and right now, he’s one of the strongest people in the entireOne Pieceworld. His journey certainly hasn’t been easy, however, and he has struggled against quite a few opponents so far.
Updated on May 15, 2025, by Rei Penber:Luffy has come incredibly far over the years, thanks to the many battles that he has fought and won. Recently, after the events of Wano, he was made one of the Emperors of the Sea and that just goes to show the level that he is on right now. However, Luffy is still far from the finished product and, as a result, he is still engaging in many high-level battles. While this list already goes over the vast majority of thetoughest Luffy fights, there are others that have managed to push him to his limits, especially now in the final saga of the story. As a result, this list of thetoughest Luffy fightshas now been updated.
Note: This list doesn’t indicate the strength of his opponents, but rather the difficulty of the fights he fought.
22Kuro
Luffy’s fight against Kuro was quite a challenge for him, especially when it came to dealing with the incredible speed the latter possessed. While Luffy was successful in landing quite a few hits on him in their fight, once Kuro tapped into the power of the Nuki Ashi technique, it became difficult for him to overcome the obstacle.
After taking quite a few hits from him and getting used to his speed, Luffy was eventually able to predict his movement pattern and counter effectively. While Kuro might not be the hardest fight he’s fought, he’s certainly one who gave him a lot of trouble quite early into the series.
21Don Krieg
Don Krieg was the captain of the Krieg Pirates and commanded the Krieg Armada, the biggest known force from the East Blue. During the Baratie arc, Krieg fought against Luffy in an enthralling battle and fared quite well.
Although not the strongest, he possessed an arsenal of weapons that made him quite dangerous. Don Krieg had access to an overpowered battle spear that gave Luffy quite a tough time, along with the MH5 gas. Although Luffy won this fight, it required every bit of his energy to overcome Krieg.
20Gecko Moria
Gecko Moria was the main antagonist of the Thriller Bark arc and one with a bounty of 320 million berries which, at the time, surpassed even Luffy’s own. Moria was quite a troublesome opponent for Luffy to deal with. During their fight, he made clever use of techniques such as Brick Bat to keep Luffy engaged.
At his strongest, evenGear Second wasn’t enough to defeat himso Luffy had to combine Gear Second with Gear Third for the very first time. At the expense of his life force, Luffy was ultimately able to take Moria down but not before passing out from exhaustion himself.
19Enel
The God of Skypiea, Enel was the main antagonist ofOne Piece’sSkypiea arc. Withthe power of the Goro Goro no Mi, he was practically invincible against everyone there, except for Luffy, who could resist his lightning powers due to his Gomu Gomu no Mi powers.
Despite being at a clear disadvantage, Enel was able to defeat Luffy once. His mantra, along with his tactical prowess in battle made him quite a foe for anyone. In the end, Luffy had to seek help from all those around him to take Enel down.
18Luffy Vs. Usopp
Luffy fought against Usopp in the Water 7 arc when the idea of replacing Merry came up. The Merry was an incredibly wonderful ship that had journeyed with the Straw Hat Pirates all the way from the East Blue to the Grand Line. However, she was reaching the end of her days and Luffy realized that, even though he wanted his best to help her. Usopp, for many reasons, did not understand this as simply and decided to leave the crew. He challenged Luffy for possession of the Merry and eventually, the two fought.
Usopp Made Luffy’s fight against him quite difficult, however, Luffy ended up winning in the end. That said, this fight was probably hard for Luffy not only because Usopp posed a great challenge, but also because it was one of his best friends who he was fighting. The emotional weight that he had to carry made it one of the most difficult fights that Luffy has ever engaged inOne Piece.
17Luffy Vs S-Bear
In the Egghead Island arc, Luffy also fought against one of the Seraphims, S-Bear, who fans know to be the clone of Bartholomew Kuma. S-Bear is quite a powerful Seraphim with the power of the Nikyu Nikyu no Mi, and, at the same time, he has also been infused with the Lunarian Lineage Factor. On top of that, his body is that of an improved Pacifista, and all these combinations make him the pinnacle of science in theOne Pieceworld.
S-Bear is so strong that even Luffy couldn’t damage him with his attacks. Of course, this fight was an extended one where Luffy was getting tired after hitting him again and again and S-Bear simply absorbed all of them since the flames on his back were on all the time. Sadly, fans did not get to see how this fight concluded. All they know is that at the end of it, S-Bear was trapped inside a bubble somehow. Fans can assume that Luffy played a significant part in that and, thus, could have won this clash.
16Luffy Vs. Lucci (Rematch)
Luffy and Rob Lucci have quite a great rivalry with each other. Fans have enjoyed this rivalry since the days of the Water 7 arc and it has only grown more intense since.In the Final SagaOne Piece, Luffy and Lucci met once again. On Egghead, Luffy was sent to assassinate Vegapunk and Luffy landed there by sheer luck. The two immediately went on to fight again. Both Luffy and Lucci were desperate to fight against each other and they immediately took their new forms.
Luffy tapped into the power of Gear 5, while Lucci showed his Awakened state to the fans. While this fight wasn’t too hard for Luffy, Lucci certainly proved to be difficult. One of his greatest assets was his recovery rate, which saw him get up again and again even after being knocked down by the future Pirate King. At the end of the fight, Luffy was left looking like an old man due to the strain that Gear 5th puts on his body.
15Luffy Vs Don Chinjao
Luffy fought against Don Chinjao, a legendary pirate worth 542 million berries, during the Dressrosa arc of One Piece. In the Corrida Colosseum, where the hunt for the Mera Mera no Mi was going on, Luffy fought a significant battle against this legendary pirate. This fight was incredibly intense and forced Luffy to push himself to use both Gear Second, and Gear Third, and utilize his Haki to the very maximum.
In the end, Luffy was able to beat him by using a powerful technique that restored the drill on his head. Chinjao then ended up becoming a loyal follower of Luffy and, currently, he is a member of the Straw Hat Grand Fleet as well.
14Luffy Vs Kizaru
Luffy and Kizaru first met during the Sabaody Archipelago Arc, however, their proper fight only happened much later in the story, on Egghead. By this point, Luffy was already declared one of the Emperors of the Sea, and, as a result, for Kizaru, this battle was an uphill task. Even though Luffy wasn’t going all out and was already carrying several injuries before the fight even began, he was still in the driving seat.
Despite that, Luffy successfully completed his mission at the end of the fight, as he was easily able to knock him down permanently.He generated so much force that Kizaru couldn’t even sit up. While Luffy himself ended up burning all his stamina, his victory over Kizaru was absolutely resounding. Furthermore, it must also be noted that Luffy accomplished this without even pushing himself to his absolute maximum.
13Sentomaru
Sentomaru made hisOne Piecedebut during the Sabaody Archipelago where he fought Luffy and managed to cause him all sorts of trouble. With incredible defense and a Haki that was especially strong, Sentomaru was able to take the brunt of the force that Luffy threw his way and counter effectively.
With his Ryuo, he could damage Luffy quite severely and, for the first time, make him consider running away from a battle. Sentomaru might not have given fans the flashiest of battles but he certainly gave fans one that saw Luffy struggle quite a lot.
