Monkey D. Luffy has had an exciting few years within the world of One Piece. As the leader of the Straw Hat Pirates and the aspiring Pirate King, Luffy’s adventures have taken him to a variety of interesting places. Just by looking at his bounty, anyone can tell that Luffy is a well-traveled individual with achievements galore and a good few stories to tell over some grog.
However, while Luffy may be pretty open about some of the most exciting elements of his journey, he may hold back more than a few details about some of his worst mistakes. This list will be going over some of the greatest things that the Straw Hat has done (and a few things that he’d rather have people forget).
10 Great: Punched A Celestial Dragon
In hindsight, this one may seem like a regrettable action given that it inadvertently led to the Straw Hats’ greatest defeat and their separation. But, if fans were to consider whether or not Luffy could go back in time and do things again, he’d most likely still punch Saint Charloss. To be even franker, he might even try and punch the guy even harder.
This scene is by far Luffy’s greatest defiance of the World Government and a strong declaration that the Celestial Dragons are no better than anyone else. Luffy was simply defending his friends here, and he could never be anything less than ecstatic about giving a helping hand…or fist.
9 Should Forget: Ate A Poisonous Fish
For people worried that Luffy‘s time in Impel Down had made him impervious to poison, here’s a scene to humble that fact. When Sanji was picked up by the Big Mom Pirates, the Straw Hats had to go on for a while without their beloved cook, leaving the cooking duties for the Sanji Rescue Squad to none other than Luffy himself.
While his first horrid dish could easily land on this list alone, Luffy made an even greater mistake by catching and eating an infamously poisonous fish. This wasn’t his proudest moment as an interim cook and proved that the crew really, really needs Sanji.
8 Great: Rang The Golden Bell
Ringing the Golden Bell isn’t the actual achievement but symbolic of the gesture as a whole. The Skypiea Arc was all about proving the impossible in the face of a hardened, disillusioned world. When Luffy rang the Golden Bell within the lost ruins of Shandora, he proved a couple of things.
Firstly, it symbolized that the Straw Hats did indeed make it to the Sky Islands. Secondly, it showed that the Sky Islands really do exist. Lastly, it also meant that the City of Gold really did exist. Having accomplished a seemingly impossible feat and finding a sight that few people had ever seen, ringing this bell must be a highlight within Luffy’s pirate career.
7 Should Forget: Got Stuck Between Some Buildings
When Nico Robin surrendered herself to CP9 during the Enies Lobby Arc, the Straw Hat Pirates panicked to get her back. They each got into action and rush to get to her side. Unfortunately, they weren’t able to keep her off the Sea Train.
Some also failed worse than others. In a dire moment for his crew, Luffy managed to slip, fall, and get stuck between two buildings in Water Seven. How this is possible is anyone’s guess, but this is a massive, slapstick quality fail in the face of one of the Straw Hats’ darkest moments. It certainly doesn’t look very good for the crew’s seemingly reliable captain.
6 Great: Challenged The World Government
Luffy more than made up for his prior faux pas with some of the most touching and grand gestures on Enies Lobby. One of the brightest things (in more ways than one) that he did was challenge the entire World Government to war by having Sniper King burn down their flag.
This not only proves Luffy’s fearlessness in the face of overwhelming odds but shows his conviction when trying to earn the respect and faith of his crew. If it takes this much just to see Robin back, he would gladly do it again.
5 Should Forget: Losing Shanks’ Arm
While Luffy wasn’t directly responsible for Shanks’ lost arm (it’s not like he personally bit it off), this is a moment that must still hang heavy on his conscience to this day. Luffy has always admired Shanks and is quick to both model the man’s look and philosophies. However, one thing that he struggled to replicate was Shanks’ humility, as he didn’t understand why Shanks would let some mountain bandits humiliate him.
This would lead to Luffy personally challenging them and inevitably getting kidnapped when the Red-Haired Pirates arrived. If Luffy was strong enough or, at least, didn’t put his nose where it didn’t belong, then Shanks wouldn’t have needed to save him and, thus, lose his arm. It was a learning moment for Luffy and a hospital visit for Shanks.
4 Great: Created Impel Down’s Greatest Prison Breaks
As a pirate, there’s not much that Luffy can do that can really shake up the pirate canon. He can certainly beat a lot of top guys and grab some treasure, but what’s really out there that can set him apart as an individual? In what is likely the most distinct and influential part of Luffy’s pirate resume to date, Luffy hosted the largest prison break in Impel Down’s history.
While simply looking to break out his brother, Portgas D. Ace, Luffy inadvertently let loose a variety of low brow criminals and historic villains to aid in his crusade. Breaking out one person is already newsworthy, but breaking out an entire army requires its own history book.
3 Should Forget: Bet His Crew
This is probably one of the most annoying parts in all of One Piece if not the crowning achievement of Luffy’s poor management skills. During the Long Ring Island Arc, Luffy was challenged by the Foxy Pirates to a Davy Back Fight, not fully understanding the context but willing to accept any challenge as it comes.
While he was able to beat the group with just the skin of his teeth the first time, the anime required some filler content and decided to make Luffy an even bigger idiot. He accepted even more challenges from Foxy the Silver Fox and began to continuously bet and lose members of his crew. If it wasn’t for the fact that the follow-up challenges were non-canon, the Straw Hats should’ve quit the crew right then and there.
2 Great: Formed The Straw Hat Pirates
In what is undoubtedly Luffy’s greatest achievement to date, he was able to start his own pirate crew and launch it to worldwide infamy. This is incredibly impressive considering his humble beginnings as just a guy getting lost on a rowboat.
Just getting each of his main crew members was a grand achievement for the lonely kid who always wanted a lot of friends. Seeing how he now leads an entire armada of pirate elites, any fan can’t help but have a tear in their eye.
1 Should Forget: Told Usopp To Leave
This is the harshest, most groan-inducing moment in the entirety of One Piece. The series doesn’t always touch on tension within the Straw Hats, but when it wants to, it keeps the rain pouring hard. After Usopp loses half of the crew’s Skypiea treasure and the rest of the crew find out that the Going Merry was irreparable, he and Luffy get into an argument about what to do next.
As captain, Luffy made the executive decision to get a new ship. Usopp, however, feeling inadequate after his earlier loss, feels that he may be next on the chopping block if Luffy is so ready to give up on the Merry. This leads to some heated words between the two, and Luffy infamously proclaims that Usopp should leave. Unfortunately, for that time, he did. Luffy doesn’t regret a lot of things, but he certainly regrets this.
One Piece's Luffy has accomplished some great things throughout the anime, but the Straw Hat captain has had his share of regrettable moments too.