For the last two decades, One Piece has managed to remain a staple of shonen manga. Noted as the highest-selling manga of all time, Eiichiro Oda’s pirate adventure story has been consistently led by the beloved main character Monkey D. Luffy, Captain of the Straw Hat pirates. He and hundreds of other pirates have dedicated their lives to crossing the Grand Line into the New World to find the coveted treasure of Gol D. Roger, the One Piece.
Luffy is one of the most famous manga protagonists of all time, beloved by millions as his undying enthusiasm for the pirate life is tried and tested. Unfortunately, there are times when his decisions do not work out in his favor.
10 RIGHT: Skypiea Was Real
The Skypiea arc began with the Straw Hat Pirates following rumors of a floating island known as Skypiea. However, it seemed the majority of people believed it to only be a fairy tale and that pirates would lose their lives searching for it. Yet, Luffy continued to believe in its existence and went on not only to find Skypiea but also battle its monarch with a god complex. He proved its existence to others by launching the Straw Hat ship from its shores, soaring through the skies.
9 WRONG: He Thought He Could Save Ace
One of the major turning points in the overarching story of One Piece was the rescue of Portgaz D. Ace. After Ace was captured by the pirate Blackbeard and handed over to the Navy, Luffy set out on a quest to rescue him. He followed Ace to the World Government super-prison, Impel Down, and to Marineford, a giant floating naval base, where Ace was killed by Admiral Akainu in the Paramount War. Luffy’s failure to save his brother was a very sudden and unexpected twist for the series as it was the first time Luffy had failed in an arc.
8 RIGHT: He Saved Robin
Nico Robin was a woman hunted by the World Government because of what she knew. She lived on an island of archivists who were studying the Void Century, a 100-year period where history was blank. When the World Government learned of this, they bombed the island and killed off all the inhabitants. Robin was the only survivor. When she reappeared as part of Luffy’s crew, the Navy set out to execute her. However, Luffy fought tirelessly to save her, even going as far as declaring war on the entire World Government.
7 WRONG: He Couldn't Defeat Magellan In Impel Down
Magellan, the warden of Impel Down, was someone Luffy lost to and never fought again. On his quest to save his brother, Ace, Luffy broke into Impel Down to stage a prison break. This was where he encountered Magellan. Magellan ate the Doku Doku no Mi Devil Fruit, which granted him poison-based powers. Luffy had no means to counter this power and outright lost this fight. He was then captured and imprisoned in Impel Down.
6 RIGHT: He Always Knew That Sanji Was His Ally
During their encounter with the Big Mom Pirates, the Straw Hats were suddenly met with the exit of one of their oldest crew members. Sanji, the crew’s cook, quit the crew to return to his family, the Vinsmokes, to attend a wedding for his arranged marriage.
He declared himself an enemy of the Straw Hats and even battled Luffy in a one-sided conflict where Luffy refused to fight back. However, after breaking up the wedding and rescuing Sanji, it was revealed that he was always their ally.
5 WRONG: Crocodile Was The First Opponent Luffy Couldn't Beat
The Alabasta arc saw the Straw Hats fall right in the center of a civil war and a crisis in the desert kingdom of Alabasta. Crocodile, one of the seven Warlords of the sea, asserted himself as the monarch of the kingdom. In order to place the true royal family back on the throne, Luffy joined the resistance and battleed Crocodile head-on. However, in their first encounter, Crocodile’s sand abilities made him untouchable as Luffy’s aggressive punching strategy failed to work. It was the first time Luffy had to step away and strategize when encountering an opponent.
4 RIGHT: He Was Right To Fight Usopp
During the Water Seven arc, Luffy and Usopp’s arguments over the fate of the Sunny, their original ship, reached a boiling point when Luffy chose to abandon the ship. Usopp challenged Luffy to a duel to decide the fate of the Sunny. Luffy accepted this challenge and fought Usopp without holding back. This showed that Usopp could be on the same level as the three strongest members of the crew, Luffy, Sanji, and Zoro. Despite Usopp's reputation as a massive coward, Luffy respected Usopp and saw him as an equal.
3 WRONG: He Stormed The Most Secure Prison On His Own
At the end of the Sabaody arc, while on the cusp of entering the New World, the Straw Hats were attacked by the Navy’s new weapon, the Pacifistas, cybernetic replicas of Bartholomew Kuma. They used Kuma’s powers to teleport the crews across the open sea. After this, Luffy learned of his brother’s execution. With such a short time window, he jumped the gun and stormed Impel Down by himself. Not only was Luffy captured, but his brother Ace was transferred to Marineford for execution. In Luffy’s escape from the prison, he also released dozens of high-ranking criminals who would join Blackbeard’s crew.
2 RIGHT: He Escaped Impel Down
Luffy was the first person to ever organize a planned escape from Impel Down, the World Government’s most secure prison. After being captured in an attempt to free Ace, Luffy explored the various levels and factions within the prison, assembled a crew of veteran pirates to successfully break out of the prison.
He then sailed all the way to Marineford in time to halt his brother’s execution. This event launched Luffy’s status as a pirate and placed him firmly on the Navy’s radar.
1 WRONG: He Underestimated Kaido
Kaido was a villain who was built up for a while. With the introduction of the four Pirate Emperors, One Piece had a new ensemble of villains for Luffy to fight. Kaido was the first one Luffy had a rivalry with after the Zou arc. While known characters like Shanks and Blackbeard were revealed as Pirate Emperors, Kaido was the immediate threat Luffy had fixated on. The fight had been built up for a long time in the story, and when he first saw Kaido, Luffy jumped straight into battle. Kaido preceded to one-shot Luffy and imprison him in a labor camp. Luffy would then need to train in preparation for fighting Kaido again.