The Straw Hat Pirates are one of the most beloved units in all of Shonen anime. One would be hard-pressed to find a One Piece fan that doesn't spew the good word of "nakama" or share tales of the Straw Hats' adventures as if they were their own. Much more than a crew, the Straw Hats are a family comprised of misfits from around the world whose individual pain and experiences help make a unit stronger than anything else.
Over the past 20 years, they've done some incredible things, such as defeat terrifying foes and craft great miracles of the sea. However, while there's plenty of opportunities to cheer them on, the fans have countless times that they've cried for the Straw Hats' hardships. This list will be looking at both sides, times the Straw Hats both beat the odds as well as went bust.
10 Could: Beating The Arlong Pirates
The Straw Hats' battle on Cocoyashi Village was perhaps the beginning of their adventures as big-league pirates. While they'd fought plenty of infamous foes up until that point, Arlong was a pirate who had plenty of cred along the Grand Line.
Relatively speaking, he was the most wanted man in the entire East Blue, with natural abilities that far surpassed humanity's who was once a crew member of one of the Seven Warlords. When the Straw Hats first beat him and his band of monsters, they took one of their biggest steps to being over-the-top Shonen heroes.
9 Couldn't: Big Mom Pirates
When Luffy and about half of the Straw Hats first infiltrated Whole Cake Island, there was a lot of ambiguity in the air about whether or not they could actually beat Big Mom. Though they never intended to clash with the Emperor, fans knew that Luffy was just destined to meet her.
As the story would have it, he did and all of the ambiguity washed away: He couldn't beat her, and his crew just hoped to escape with their lives. There were plenty of big victories along the way; but if this arc proved anything, it's that the Straw Hats are going to have to step things up if they're gonna take on Kaido.
8 Could: Beating Baroque Works
While the Arlong Park Arc was the first major arc of the series, Alabasta is what many fans herald as the beginning of One Piece's true acclaim. It was a grand saga that not only pitted the Straw Hats against some of the sea's most treacherous bounty hunters but also an actual member of the Seven Warlords, Sir Crocodile.
They not only got to beat bounty hunters who've hunted down people with 50 million beli bounties and above but got to prove that they themselves were worthy of big-time bounties. While fans didn't know it at the time, beating Crocodile was the moment that Luffy became a Supernova.
7 Couldn't: Bartholomew Kuma On Thriller Bark
Though their time on Alabasta proved that the Straw Hats could take on the Warlords, they don't exactly have a clean record throughout the series. One of the biggest examples of this is their unfortunate encounters with Bartholomew Kuma.
Right after they narrowly beat the Thriller Bark Pirates, they were immediately attacked by Bartholomew Kuma, who didn't even break a sweat keeping the tired Straw Hats down. When everything seemed forgone, what really saved the Straw Hats was a grand gesture from their very own Pirate Hunter. Not all of Zoro's badass moments need to be victories.
6 Could: Reaching Skypeia
When the Straw Hats first started to look for Skypeia, everyone laughed at them. Skypeia was supposedly a fantasy island, and any association with it was merely chocked up to pure coincidence per the world's weird science. However, the Straw Hats persisted and found their own creative way to reach the islands in the sky.
They attached wings to the Going Merry and had it ride up a Knock Up Stream, a literal sea eruption that could destroy islands. Not only were the Straw Hats able to beat the scientific odds, but they did, in fact, find the fantasy world that few adventurers had ever seen.
5 Couldn't: Aokiji
While the Straw Hats' adventure to Skypeia truly took them to heaven, their ride down was a harsh fall to earth. One of their first confrontations after returning to the Blue Sea pitted them against one of the top-ranked Marines, Admiral Aokiji. It was a major opportunity for the Straw Hats to prove themselves against one of the top figures in the world.
What they proved, however, was that they were still guppies within a larger sea. Aokiji was able to single-handedly take on the Straw Hats' best attacks and barely had to move to do so. It was a great showing for what was to come in the One Piece story, and a great way to humble the Straw Hats after they just beat a god.
4 Could: Saving Nico Robin
The Straw Hats didn't have to wait too long before their next big confrontation with the Marines. When they arrived at Water Seven, Nico Robin was immediately identified by an undercover force already plotting to disrupt the island's daily life. In the Straw Hats' effort to protect Nico Robin from the World Government, they were poised against their elite spy force, Cipher Pol 9.
Doing so would require them beating literal superhuman spies whose physical strengths and skills immediately outclassed their own. Towards the end of the Enies Lobby Arc, they even had to outrun the dreaded Buster Call attack that once erased Robin's home of Ohara. This was the beginning of the Straw Hats directly challenging and beating the World Government as well as facilitating Nico Robin as a full member of the crew.
3 Couldn't: Going Merry
Even though the Straw Hats were able to save Nico Robin, the same can't be said for their beloved first ship, the Going Merry. The whole reason that they entered Water Seven was to get their precious ship repaired by some of the finest engineers and shipwrights around. However, they only learned that the Going Merry had sustained irreparable damage after the Straw Hats' cavalier adventures.
Since the sobering diagnosis, the fans were left wondering if the Straw Hats would truly abandon their wooden family member or if they would miraculously be able to save it. They couldn't. The result was one of the saddest scenes in One Piece history and the beginning of the Thousand Sunny era.
2 Could: Reaching The New World
While reaching Skypeia was an otherworldly achievement within its own right, the Straw Hats' biggest milestone to date is when they finally reached the New World. During the East Blue Arc, the Grand Line was teased as this insurmountable force within its own right that even some of the sea's most experienced adventurers couldn't overcome.
For a young and fresh crew who had only traveled the Grand Line for a total of six months, the Straw Hats were able to reach the halfway mark. It was the beginning of the Straw Hats being taken seriously as a truly big-time pirate crew. Though they had to wait until they could fully enter the New World, their eventual arrival got to symbolize genuine progress for them as individuals and as a unit.
1 Couldn't: Bartholmoew Kuma On Sabaody Archipelago
However, the entire reason that they had to wait in the first place was primarily because of a devastating defeat by one man in particular. Kuma wasn't quite down with the Straw Hats after Thriller Bark. After Luffy punched a Celestial Dragon, he incurred the full wrath of the World Government and immediately had a Marine Admiral and the government's new line of cyborgs stalk Sabaody Archipelago.
The Straw Hats struggled enough with taking on one Pacifista, but Kuma came in to take them down in one fell swoop. This is seen as the Straw Hats' greatest defeat yet and the major inspiration for their two-year training period.