Monkey D. Luffy is the captain of the Straw Hat Pirates and the protagonist of the One Piece series. As seen throughout One Piece Luffy isn't the smartest pirate in the story and he sometimes makes things worse. When the need arises, Luffy is extremely sharp, but his decision-making is questionable to say the least.
Luffy often invites trouble without thinking twice. On occasion, Luffy's made an already bad situation even worse for the Straw Hat Pirates – but that's life in One Piece.
10 Luffy Got Stuck In A Bird's Mouth On The Way To Orange Town
After joining up with Zoro on Shell's Town, the two had no crew and very little idea of what they wanted to do next. An already bad situation was made even worse when Luffy got carried away by a bird to Orange Town. There, Luffy met Nami and was tricked by her quite easily. All of his decisions in Orange Town created a lot of problems for Zoro and even Nami to an extent.
9 Luffy Fell Asleep Fighting Black Cats Pirates
The Black Cats Pirates were certainly not easy for Luffy to take and Django's trickery made it even harder for him to fight against them. After tearing out the hull of their ship to fight them, Luffy was put to sleep by Django quite easily and spent the majority of the fight asleep. In the meantime, Zoro, Nami, and Usopp faced a lot of trouble at the hands of the Nyaban brothers and Kuro himself.
8 Luffy Trapped Himself In The Fight Against Arlong
Luffy's fight against Arlong would've ended a lot earlier had Luffy not created problems for himself. To take down Moomoo, Luffy stuck his feet into the ground and swung the beast, only to later not be able to free himself. Arlong immediately threw him into the water and it took quite a lot of work to get out. Sanji had to survive Kuroobi's assault and then break stone underwater to free Luffy so he could finally fight.
7 Luffy Almost Got Executed In Loguetown
Luffy's time in Loguetown was certainly not pleasant as he was almost executed by Buggy and Alvida on the same spot as Gol D. Roger 24 years ago. Thankfully, Monkey D. Dragon was around and used his powers to save Luffy from imminent death.
Without Dragon, Luffy would've died before even reaching the Grand Line and put his entire crew in quite a lot of danger, with Marines such as Smoker surrounding the place already.
6 Luffy Walked Right Into Crocodile's Path In Rain Dinners
In the Alabasta arc, Luffy attempted to carve his way open to Crocodile when he reached Rain Dinners and instead found himself locked in a sea-prism stone cage. What's surprising is the fact that Luffy willingly walked into Crocodile's trap, as did the rest of his crew. Every single member who was trapped in the cage would've died had it not been for Sanji's clever plan to get them out. Once again, Luffy made the situation quite troublesome.
5 When He Let His Shadow Get Taken By Moria
Gecko Moria was the main antagonist of the Thriller Bark arc. As a Shichibukai, he proved to be quite a challenge for Luffy and his crew. When the crew set foot on Thriller Bark, they had little idea of where to go and what to do next. As expected, Luffy made the situation much worse by getting captured. Immediately afterward, Luffy's shadow was stripped off him by Moria and used to animate Oars, the legendary continent puller. Oars created all sorts of problems for the Straw Hat Pirates, all because Luffy was careless.
4 Luffy Toyed Around With Caesar Clown For Too Long
The Punk Hazard arc of One Piece saw Luffy go head-to-head against Caesar Clown. As seen throughout One Piece Luffy isn't the smartest pirate in the story and he sometimes makes things worse.
Luffy purposely let him put up a fight and when Caesar removed the oxygen from the air, Luffy ended up losing the fight and getting captured.
3 Luffy Entered The Corrida Colosseum To Win The Mera Mera No Mi
One Piece's Dressrosa arc saw Luffy fight in the Corrida Colosseum in order to win Ace's Mera Mera no Mi. Despite knowing it was a trap, Luffy had no choice but to fight there. Doflamingo had already predicted this and made it such that Luffy wouldn't escape in the first place. Thankfully, Luffy was helped by Bellamy, Bartolomeo, and most importantly, his brother Sabo. Without them, he would've been stuck there until he got turned into a toy.
2 Luffy Didn't Use Gear Fourth Against Doflamingo Right Away
Luffy's fight against Doflamingo was quite a difficult one, but only because he made it out to be. After already having wasted a lot of Haki , Luffy continued to use pointless attacks against Doflamingo and kept wasting his Haki and stamina. When Luffy got serious and used Gear Fourth, he was already too tired to finish Doflamingo off. Had Luffy used Gear Fourth straight away, Doflamingo would've been defeated easily and the Birdcage would've stopped a lot sooner.
1 Luffy Attacked Kaido In A Fit Of Rage In Wano Country
Luffy's first fight against Kaido came in Kuri when he witnessed the Yonko attack his crew. Not holding anything back, Luffy risked destroying the entire plan that the Akazaya worked hard towards by attacking Kaido. Even when he threw everything that he had at him, Luffy was unable to hurt Kaido, and eventually was defeated with a single swing of Kaido's kanabo coated in Conqueror's Haki. Luffy ended up in Udon Prison and made the alliance's plan a lot more difficult to pull off.