The sprawling story of One Piece is loaded with brutal and exciting fights, and for the sake of suspense and balance, Luffy and his Straw Hat allies usually win by the skin of their teeth. The Straw Hats were pushed to the brink against Gecko Moria and Oars' zombie, for example, and defeating Sir Crocodile took Luffy three different tries to accomplish.
The East Blue Saga's villains may seem like small fry compared to the four Emperors or the three main Admirals in hindsight, but at the time, they were pretty tough foes for the small Straw Hat crew to face. Luffy and his first four crewmates faced their first real challenges against these early foes, and they needed all their grit, strength, and ingenuity to win.
10 Luffy Vs. Captain Morgan Took Some Effort
Overall, Luffy's fight against the cruel Captain Axe-Hand Morgan wasn't that tough, but it was still more challenging than taking on ordinary Marine troops. Luffy arrived at Shells Town and met the captive swordsman Roronoa Zoro and swore to free him from Morgan's and Helmeppo's grasp.
Luffy didn't have his Gears or Haki in this fight, but he didn't need them. He simply used his rubbery offensive techniques and mobility to keep pace with the formidable Morgan, then claimed victory after some effort. He even knocked over Morgan's tax-funded statue to seal the deal.
9 Roronoa Zoro Vs. Cabaji Was A Bloody Circus Fight
In Orange Town, Luffy and Zoro confronted the Buggy Pirates, led by Buggy the Clown himself. Zoro fought a scarf-wearing Buggy pirate named Cabaji, who usually rode on a unicycle in battle. Cabaji fought dirty, using Zoro's wounds against him to get the edge.
Zoro had a tough time against Cabaji at first, and Cabaji could even use a flame-breath attack to make things worse. Eventually, though, Zoro knocked Cabaji off his unicycle with his oni giri attack to the chest, which settled the fight with a Zoro victory.
8 Luffy Vs. Buggy The Clown Was Tough, But Not Too Serious
Buggy the Clown wasn't terribly powerful in Orange Town, but he and his men did use tricks to even the odds against the powerful Luffy/Zoro duo. Buggy's Chop-Chip Fruit made him immune to Zoro's swords, and even Luffy's fists had a tough time hitting the split-up Buggy.
Luffy even got locked in a cage, and he nearly got shot with a cannon point-blank. Eventually, he got free, and he resumed this tricky battle against Buggy to decide Orange Town's fate. With a few low blows, such as kicking Buggy between the legs, Luffy scored a hard-won victory.
7 Roronoa Zoro Vs. Buchi & Sham Really Tested Zoro's Skills
When the tiny Straw Hat crew arrived at Syrup Village's island, they met the notorious liar Usopp, then helped Usopp defend the village from the dreaded Black Cat Pirates. This protracted battle included a 2-versus-1 fight where Zoro took on the Nyaban/Meowban brothers, Sham and Buchi.
Zoro did well, considering the odds, and he had little to fear from the brothers' cat claws and fists. The fight got much tougher, though, when Jango used his hypnosis to make Buchi and Sham much stronger. Zoro worked up a real sweat defeating them after that, but he pulled it off.
6 Luffy Vs. Captain Kuro Pitted Luffy's Rubber Against Ten Sword-Claws
Eventually, the battle for Syrup Village boiled down to each side's strongest fighter and leader, Luffy of the Straw Hats and Captain Kuro of the Black Cat Pirates. Captain Kuro was leaps and bounds faster and more skilled than any of his crew, and he had special gloves where each claw was a full-sized sword blade.
This was Luffy's toughest fight yet, though he evened the odds somewhat when he used a rock to break half of Kuro's claw blades. Kuro even unleashed his ultimate move, going into a deadly frenzy to slice up everyone around him, but Luffy fought back and prevailed against fearsome odds.
5 Sanji Vinsmoke Vs. Pearl Showcased Sanji's Skills In Mortal Combat
The Baratie story arc introduced the Baratie restaurant ship and its crew, including the tsundere chefs Sanji Vinsmoke and Chef Zeff. Then the tattered but huge Krieg Pirates crew arrived, and Krieg and his officers made harsh demands of the Baratie's staff.
Sanji dived into the fray, taking on Pearl, a Krieg pirate with tough armor and shields. Sanji did well with his kicking techniques, but Pearl gave as good as he got. Ultimately, it was Gin who settled the fight instead, defeating Pearl because he wanted to finish off Sanji himself.
4 Roronoa Zoro Vs. Hatchan Was A Clash Of Many Blades
In the Arlong Park story arc, Luffy's small crew hurried to Nami's home island so they could rescue Nami from Arlong's wrath. First, though, Luffy's crewmates Zoro and Usopp took on Arlong's top lieutenants, including Zoro's fierce sword battle with Hachtan.
Like Zoro, Hatchan was a swordsman who used far more than one weapon in battle. With his many arms, Hatchan had more blades than Zoro himself. That, combined with Hatchan's advanced skills and fish-man strength, made this a tough fight for Zoro to win, but Zoro managed it.
3 Usopp Vs. Chew Was Usopp's First Solo Victory
Usopp is a support fighter who usually backs up his fellow Straw Hats with his ranged techniques and tricks, such as exploding stars and even tabasco sauce shots. In Arlong Park, Usopp had to face Chew the fish-man all alone, and Chew brutally beat him.
Usopp refused to give in. He knew he was outmatched, but with Nami and the village at stake, he couldn't afford to lose. Usopp used all his wits to finally turn the tables on Chew and score his first solo victory, a painful but hard-won victory that Usopp reveled in.
2 Luffy Vs. Don Krieg Was A True Test Of Rubber Vs. Armor
Just like in Syrup Village, Luffy found himself fighting captain to captain to resolve an entire story arc's conflict. Captain Kuro was a formidable foe, but Don Krieg was on another level with his powerful body, suits of armor, fancy shields, and weapons of war.
Luffy struggled mightily against Don Krieg's impressive weapons and defenses, and for a time, it seemed hopeless. Then Luffy pulled off a miracle and punched his way through Don Krieg's spiked armor shell, taking down that warlord captain once and for all.
1 Luffy Vs. Arlong Was The East Blue Saga's Highlight
For the third and final time in the East Blue saga, Luffy resolved a story arc in mortal combat, captain vs. captain. Zoro and Usopp had done well against Arlong's officers, but only Luffy was in shape to finish the fight and take on the mighty Arlong directly.
Arlong was a vastly powerful opponent with enormous fish-man strength, including his ultra-strong jaws and his shark-like teeth. Luffy suffered many blows and nearly drowned at one point, but with sheer grit, he turned the tables. He defeated Arlong and symbolically destroyed Nami's cartography office at the same time, freeing Nami as Arlong's reluctant cartographer.