The Strawhats' journey has been an arduous one. They started from the very bottom and climbed stage after stage, but faced difficulties throughout each stage. They ventured all the way from East Blue to the samurai's country of Wano.

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The number of challenges they faced was numerous and the number of challengers, even more. When you are a pirate, and a rookie at that, you get picked on by just about anyone. At times, the Strawhats would come out triumphant from these ordeals. Other times, they were overpowered and suffered a bitter defeat. At rare times, when you thought they were winning, they unexpectedly lost instead. Let's countdown these rare occasions where we thought the Strawhats would win, but they didn’t.

10 Zoro Vs Enel

We were introduced to Enel, the god complex logia user, at Skypiea arc. The devil fruit he ate goes by Rumble-rumble fruit. The fruit is a logia type and it grants Enel the properties of electricity.

Being the main antagonist of the arc, Enel was destined to be taken down by Luffy. But when Zoro charged at Enel all of a sudden, some fans speculated otherwise. And these speculations were shot down pretty quickly because Zoro was unexpectedly One-Shotted.

9 Luffy vs Smoker

Smoker, a marine captain at that time, served as a major antagonist in the Logue Town arc. The arc featured a variety of antagonists, including Buggy and Alvida. But Smoker was undoubtedly the strongest of the antagonists available.

Instead of a badass, 3 episodes long boss fight between Luffy and Smoker, all we got was Luffy getting one-sidedly beaten down. And if it wasn't for Dragon's intervention, things would've turned even stickier for Luffy.

8 Sanji vs Judge

sanji vs judge

As we all know, Sanji had some serious family issues. A miserable childhood is not enough to describe what the cook went through as a youngster. All kinds of abuse, both verbal and physical. Sessions of bullying and torture from the so-called siblings. and even extreme punishments like imprisonment. Sanji obviously needed to vent. And who was a better outlet to vent at other than the main culprit, Vinsmoke Judge.

Every fan expected and hoped for Judge to get a good thrashing. But we were disappointed when Judge resorted to underhanded means and somehow counter defeated Sanji. A definite bummer.

7 Strawhats vs Aokiji

aokiji freezes robin in one piece

The Long Ring Long island arc was a fairly uneventful arc though being a prelude to one of the best sagas in one piece, the water 7 saga. At some point during the arc the strawhats randomly stumbled upon Aokiji. And to be fair, everyone expected him to be just another marine asking for a beating, but we were proven wrong rather quickly. It all ended in a flash. And if not for Aokiji's Mercy, the strawhats would've been wiped out.

6 Luffy vs Magellan

Magellan is definitely a big boss kind of character. He was the warden of the infamous Impel Down prison, but later got demoted for his blunders. But if one underestimated Magellan, then they are definitely up for a painful lesson.

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Luffy had a brief exchange with Magellan at some point during his rampage at Impel Down and was nearly killed in the process. Sometimes defeating the main antagonist of an arc is just not possible, and Luffy learned that the hard way.

5 Zoro and Luffy vs Fujitora

Luffy vs Fujitora

Issho, who goes by Fujitora, is a marine admiral who enrolled after the time skip. And like anyone who had the admiral rank, Fujitora is a force to reckon with.

Fujitora served as an antagonist in the Dressrosa arc. He had a brief exchange with both Luffy and Zoro, but it never went past being a skirmish. As much as fans hope for the Strawhats to defeat a Marine admiral, it’s not happening, at least not yet.

4 Strawhats vs Big Mom

Big Mom steals someone's soul in One Piece.

The whole cake island arc received various critiques. Some being positive while others negative. Regardless of how you think of it as an arc, everyone shared a mild disappointment. Though it was unrealistic for Luffy to defeat a Yonko this early on. The fans still had a tiny fantasy regarding the concept.

The strawhats might have lost a battle against Big Mom, but they at least won the war at Whole cake island.

3 Kuma vs Strawhats

Shichibukai Bartholomew Kuma only encountered the strawhats twice. And at these two meetings, he utterly overwhelmed them.

Some had the fair argument that if the strawhats weren't so spent from their bout against Moria and his minions, they might've stood a chance against Kuma. But that argument was proven invalid rather quickly when Kuma suddenly appeared at Sabaody Archipelago and took the strawhats down for the 2nd time.

2 Luffy vs Kaido

Luffy punches Kaido- Wano One Piece

The Wano arc made a buzz amongst the One piece communities like no before. Many speculate that the war at Wano is destined to make the Paramount war look like a friendly spar. Some fans even theorized that major players Like Golden Lion Shiki might be making an appearance later on at Wano.

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A brief confrontation between Kaido and Luffy occurred early on at Wano, and the results were shocking to say the least. It was beyond all fans’ expectations to see Luffy getting one-sidedly massacred by Kaido.

1 Marineford's Paramount war.

The Marineford arc is one of the best arcs in one piece, if not the best. The arc featured so many events that it could only be dubbed as iconic. The main drive behind the Paramount war was Portgas D. Ace. And If Ace was to somehow die, the entire war would be pointless. Or so everyone thought before getting hammered but the harsh reality.

Ace's death at the end of the arc wasn't only shocking to Luffy, it was shocking to the entire fanbase.

NEXT: One Piece: 10 Characters Who Are Pirate King Material