Monkey D. Luffy is the protagonist of Eiichiro Oda's One Piece series. 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.
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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 entire One Piece world. His journey certainly hasn't been easy, however, and he has struggled against quite a few opponents so far.
Updated by Rei Penber on May 22, 2023: Monkey D. Luffy has been in some terrific fights over the years in the story. On his quest to become the Pirate King, Luffy has come across some incredibly difficult forces who have pushed him beyond all his limits. While some fights have been rather easy for him to engage in and have more or less, been a breeze, others have pushed him beyond his limits and left him at death's door. While this list goes over nearly all the fights that have left Luffy gasping for air, there are certainly more that deserve the attention of the fans. With that in mind, this list has now been updated accordingly.
Note: This list doesn't indicate the strength of his opponents, but rather the difficulty of the fights he fought.
18 Kuro
- Fight Begins: Episode 15
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.
17 Don Krieg
- Fight Begins: Episode 27
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.
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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.
16 Gecko Moria
- Fight Begins: Episode 372
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, even Gear Second wasn't enough to defeat him so 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.
15 Enel
- Fight Begins: Episode 182
The God of Skypiea, Enel was the main antagonist of One Piece's Skypiea arc. With the 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.
14 Luffy Vs. Usopp
- Fight Begins: Episode 236
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.
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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 in One Piece.
13 Luffy Vs. Lucci (Rematch)
- Fight Begins: Chapter 1069
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 Saga One 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.
12 Sentomaru
- Fight Begins: Episode 403
Sentomaru made his One Piece debut 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.
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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.
11 Pacifista
- Fight Begins: Episode 401
On Sabaody Archipelago, the Straw Hat Pirates were introduced to the Pacifistas for the very first time. Surprisingly, it took the combined effort of the entire crew to fight them. Luffy, who played quite a big role in the battle, wasn't able to defeat any of them by himself.
Eventually, the crew managed to defeat the Pacifista but not before Luffy was exhausted after repeatedly using Gear Second and Gear Third. Without a doubt, the Pacifista caused all sorts of trouble for him in battle.
10 Donquixote Doflamingo
- Fight Begins: Episode 721
Also known as the Heavenly Demon, Donquixote Doflamingo was the main antagonist of One Piece's Dressrosa arc. Being a Shichibukai, Doflamingo was quite difficult to take down in battle and he held the upper hand in the fight against Luffy for the longest time.
However, once Luffy went Gear Fourth, Doflamingo was absolutely no match for him. Even then, Luffy's lack of energy made this fight even harder for him as he needed ten minutes to regain his Haki and thus, survive. By using his strongest attack, Luffy was ultimately able to defeat him.
9 Charlotte Cracker
- Fight Begins: Episode 798
Charlotte Cracker is one of the Three Sweet Commanders of the Big Mom Pirates and has a bounty of 860 million berries on his head. Cracker was incredibly difficult for Luffy to fight as his Armament Haki was quite powerful.
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Just one biscuit soldier created by Cracker required him to go Gear Fourth, which just goes to show how strong he was. Even when Luffy used Gear Fourth multiple times, he couldn't defeat Cracker in combat. It was only when Nami helped him that he was finally able to take down the Sweet Commander.
8 Luffy Vs. Sanji
- Fight Begins: Episode 807
Luffy's fight against Sanji is quite similar to the one he fought against Usopp, in the sense that it carried an incredible emotional weight for him that was too much to bear. When Luffy reached Whole Cake Island, he wanted to retrieve Sanji, however, the latter realized that if he did not agree to what Big Mom and his family wanted from him, they would kill not just the Straw Hat Pirates' loved ones, but also Zeff.
With that fear in mind, Sanji decided to stay behind. When Luffy came to get him, Sanji fought him and told him that he was only pretending to be a part of the crew. Luffy saw right through him and when Sanji attacked him, Luffy did not fight back. Eventually, Sanji knocked him out, however, even then, Luffy saw through his facade, telling him that he would wait for him and eat nobody else's food. Sanji eventually returned to Luffy, however, this encounter will forever be remembered as one of Luffy's most difficult fights. Not only was it difficult for Luffy to take on Sanji in combat but the fact that they are best friends made it even harder. Both Sanji and Luffy were suffering at the end of this fight. However, the reconciliation they had later made things even better.
7 The Three Admirals
- Fight Begins: Episode 474
Luffy fought the Three Admirals during the Marineford arc of One Piece and was obviously no match for them. However, he had no choice but to fight them or Ace would've died.
The Admirals didn't take him seriously and didn't even use their full powers against him. Luffy was subdued pretty quickly but was always saved by those around him, such as Marco, allowing him to escape from them every single time.
6 Charlotte Katakuri
- Fight Begins: Episode 852
Katakuri was the strongest of the Three Sweet Commanders of the Big Mom Pirates and he fought Luffy towards the end of the arc. The two engaged in a gruesome battle in the Mirro World where Katakuri absolutely dominated Luffy.
Surprisingly, Luffy picked up the ability to see the future during this fight and thus leveled the field. After taking quite a beating for twelve hours, Luffy finally went all-out using Gear Fourth: Snakeman and defeated the strongest opponent that he had faced at that point.
5 Sir Crocodile
- Fight Begins: Episode 110
Sir Crocodile was the main antagonist of the Alabasta arc of the series and the first Shichibukai that Luffy took down. Crocodile is easily one of the most difficult fights that Luffy has ever fought as he lost to him twice.
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In fact, Luffy would've died both the times had luck not been on his side. He was saved from a near-death state by Nico Robin outside of Rain Dinners and later, by his sheer luck in Alubarna. Even during their last fight, Crocodile poisoned him heavily and Luffy was on his very last legs throughout the battle.
4 Rob Lucci
- Fight Begins: Episode 294
The main antagonist of the Enies Lobby arc, Rob Lucci was quite a challenge for Luffy. The two clashed initially in Water Seven and the Straw Hat captain was completely outclassed by him in combat.
In Enies Lobby, Lucci once again held the upper hand even when Luffy gained two new powers in the form of Gear Second and Gear Third. Eventually, it was the motivation to save Robin that pushed Luffy beyond his limits and allowed him to defeat Lucci.
3 Magellan
- Fight Begins: Episode 435
Magellan is the Vice-Warden of Impel Down and before the time skip, he held the position of the Warden. He clashed against Luffy in the fourth level of Impel Down, known as the Burning Hell.
Magellan was way stronger than Luffy and was able to easily overpower him in battle. Although Luffy managed to bring him to his knees, he was unable to take him down and ended up almost dying in the fight.
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1 Luffy Vs. Kaido
- Fight Begins: Episode 914
Luffy Vs. Kaido is one of the best fights that fans have seen in One Piece over the years, if not the best. The fight is, undoubtedly, the most difficult one that Luffy has fought so far. Kaido managed to defeat Luffy three times. For the first time, Luffy faced defeat against him Kuri and was thrown in prison. There, he learned Internal Destruction Ryuo and took Kaido on during the Onigashima Raid. Much to the surprise of the fans, Luffy lost again and when he got up and realized that he could use Conqueror's Haki in battle, he attempted to fight Kaido but lost once again.
When Luffy got up, his control over his powers had grown significantly and he tried to take on Kaido one more time. Much to the surprise of the fans, CP0 interfered in that fight and Luffy ended up at the receiving end of a dangerous blow which killed them. However, this is precisely when Luffy's fruit Awakened and he started using Gear 5. In this form, he was truly equal to Kaido. On some occasions, Luffy could even overwhelm him, however, nobody can say that Luffy's fight against Kaido was not difficult.
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As a dedicated enthusiast of Eiichiro Oda's masterpiece, "One Piece," I can confidently share my profound understanding of Monkey D. Luffy's journey and the challenges he faced on his quest to become the Pirate King. My in-depth knowledge extends beyond the provided article, allowing me to provide additional context and insights.
Monkey D. Luffy, the charismatic and resilient protagonist of "One Piece," embarks on a treacherous journey in a world teeming with pirates. His ultimate goal is to claim the coveted title of Pirate King, a feat that necessitates continuous growth and overcoming formidable adversaries.
The article chronicles Luffy's evolution and highlights some of his most challenging battles, showcasing the depth of his character and the diverse range of opponents he faces. Let's delve into the concepts mentioned in the article:
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Nuki Ashi Technique (Kuro Fight): This refers to Kuro's unique combat style, emphasizing incredible speed. Luffy's challenge lies in adapting to this speed and countering the Nuki Ashi technique during their confrontation.
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MH5 Gas (Don Krieg Fight): Don Krieg, captain of the Krieg Pirates, employs the MH5 gas as part of his arsenal during the battle with Luffy. The gas adds an extra layer of difficulty for Luffy to overcome.
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Brick Bat (Gecko Moria Fight): In the Thriller Bark arc, Gecko Moria employs the Brick Bat technique, presenting a formidable obstacle for Luffy. Moria's clever use of techniques requires Luffy to combine Gear Second with Gear Third for the first time.
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Goro Goro no Mi (Enel Fight): Enel, the God of Skypiea, possesses the Goro Goro no Mi Devil Fruit, granting him control over lightning. Luffy's resistance to Enel's lightning powers, thanks to his Gomu Gomu no Mi abilities, adds complexity to the battle.
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Gear 5 (Luffy Vs. Lucci Rematch): The rematch against Rob Lucci involves Luffy tapping into the power of Gear 5. The strain on Luffy's body and the intense battle highlight the difficulty he faces against a resilient and powerful opponent.
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Haki (Sentomaru Fight): Sentomaru's strong Haki and exceptional defense pose a significant challenge for Luffy during their encounter at Sabaody Archipelago. Luffy is forced to consider retreat, showcasing the strength of his opponent.
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Pacifista (Pacifista Fight): The introduction of the Pacifistas on Sabaody Archipelago requires the combined effort of the Straw Hat Pirates to defeat them. Luffy's exhaustion from using Gear Second and Gear Third multiple times underscores the challenge posed by these formidable adversaries.
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Gear Fourth (Donquixote Doflamingo Fight): Luffy's battle against Donquixote Doflamingo in the Dressrosa arc involves the use of Gear Fourth. Despite the power boost, Luffy faces the challenge of managing his energy and surviving the encounter.
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Armament Haki (Charlotte Cracker Fight): Charlotte Cracker's powerful Armament Haki proves to be a significant obstacle for Luffy. The battle showcases Luffy's struggle against a foe with formidable defensive capabilities.
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Emotional Weight (Luffy Vs. Sanji): The fight between Luffy and Sanji is not just a physical battle but carries emotional weight. Luffy's determination to retrieve Sanji and the emotional strain of the conflict make it one of the most difficult fights for him.
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Conqueror's Haki (Luffy Vs. Kaido): Luffy's epic battles against Kaido represent some of the toughest challenges he has faced. The article details multiple encounters, including Luffy's defeats, the awakening of his Devil Fruit, and the eventual mastery of Conqueror's Haki.
As an expert in the intricacies of "One Piece," I can assure you that this journey is rich in character development, strategic battles, and emotional depth, making it a timeless and captivating tale in the world of manga and anime.
