The Worst Generation was a group of unrelated pirates who all arrived on Sabaody Archipelago at the same time. Although seemingly irrelevant at first, they later played massive roles in One Piece's New World saga.
Throughout Luffy's adventures, he has made friends and enemies with the Worst Generation's other captains. Their varying levels of intelligence have been both a boon and a detriment, with many forging temporary alliances of convenience.
10 Luffy Is Notorious For His Bad Decisions
Despite being the strongest member of the Worst Generation, Luffy's judgment leaves much to be desired. He will constantly leap into situations without understanding them and trust people who do not deserve his trust. In many cases, Luffy's actions have put his crew at direct risk.
For example, he attracted the marines to the Sabaody Archipelago by punching Charloss. Should Kuma not have been there to save them, Kizaru would have captured and likely executed the Straw Hats. Unfortunately, two years have done little to quell Luffy's spontaneous and impulsive nature.
9 Urouge Doesn't Have Much Of A Plan
"Mad Monk" Urouge was a giant man who wielded a large, pillar-like weapon. Out of the entire Worst Generation, he seems the least focused on a single goal. Instead, he wanders about encountering various threats and testing his mettle against them.
To Urouge's credit, he's at least competent enough to defeat Sweet General Cracker. However, his lack of a palpable objective means that the other captains are at a far greater advantage than he is. This will inevitably reflect in their bounties as they rise to prominence while he falls from it.
8 X Drake Was A Failure Of A Spy
X Drake masqueraded as a member of the Worst Generation so that he could keep an eye on them for the World Government. When ambushed by Kaido, he was conscripted into the Beast Pirates and joined willingly. For Drake, the only thing this changed was the nature of the information he'd be relaying.
Unfortunately, Drake was a relatively useless spy. He didn't relay particularly useful information that CP0 wouldn't have known otherwise and got exposed by Queen shortly into the Onigashima invasion. In the end, not even the Straw Hats fully trusted him due to his duplicitous nature.
7 Scratchman Apoo Is Fairly Shallow But Prudent
"Scratchman" Apoo was a musician in service of the Beast Pirates. Unlike Hawkins or Drake, he joined them willingly in hopes of becoming an influential member. However, Apoo drastically overestimated the benevolence of Kaido and his henchmen.
During the Onigashima invasion, he was completely unprepared for Queen's betrayal or the hordes of people who would pursue him for the ice oni antidote. Having betrayed the Worst Generation and been betrayed by the Beast Pirates, Apoo is now even more alone than X Drake. His lack of a crew certainly doesn't do him any favors.
6 Kid Was Smart But Impetuous
Like Luffy, Captain Kid was often too reckless for his own good. He drew unnecessary attention to himself constantly, whether attempting to show off against the marines at Sabaody or standing up to Kaido when no one else did.
However, Kid is significantly more cunning than what most give him credit for. He managed to escape Udon well before Luffy did and nearly killed Big Mom by himself by identifying Zeus' weakness. Cunning and underhanded, Kid will make a difficult opponent if he and the Straw Hats ever become enemies.
5 Hawkins Makes The Most Logical Choices He Can
Hawkins often takes the most prudent choice, such as attempting to flee Sabaody and aligning with Kaido when confronted by him. When combined with his fortune-based affinities, this suggests that he will survive longer than many other members of the Worst Generation.
However, Hawkins' urge to make safe decisions is at the expense of his ambitions. Therefore, even though he may be marginally smarter than other pirates, his reluctance to put his intellect to good use is a major credit against him.
4 Jewelry Bonney Knows How To Get Out Of Bad Situations
Despite being the unluckiest member of the Worst Generation, Jewelry Bonney knows how to get out of a pinch. She escaped Blackbeard, prevented Charloss from murdering Zoro, and even infiltrated the Reverie by posing as an old woman. This conveys her intelligence in an extremely favorable light even if she has not appeared as frequently as other Supernovas.
Recently, Bonney enlisted the aid of the Straw Hat Pirates on Egghead Island. Considering their track record of success, Bonney's choice of allies is sure to produce favorable results.
3 Trafalgar Law Is A Prudent Young Man With Great Judgment
Trafalgar Law's ability to keep a level head allows him to survive the direst of situations. Whether escaping at Sabaody or in Marineford, he uses his Devil Fruit to guarantee the safety of his crew in almost every situation.
Law also understands how to employ his abilities intelligently in a fight. For example, he swapped his own body with one of Doflamingo's henchmen in order to misdirect the warlord's attacks. Once Doflamingo was satisfied that Law had died, Law switched places again and helped Luffy launch a counterstrike.
2 Bege Was A Brilliant Cutthroat From The West Blue
"Big Gang" Bege embodies everything it means to be a pirate and gangster. In his youth, he quickly attained a reputation as a deadly criminal by betraying others and seizing their criminal empires. He proved equally treacherous during the Whole Cake Island arc when attempting to assassinate Big Mom alongside the Straw Hat Pirates.
Given the extensive research he conducted into the emperor's weakness, he came stunningly close to finishing her off in spite of his otherwise low offensive potential. Bege's duplicity was not completely selfish. He also wanted closure for his wife, who Big Mom unfairly made a target.
1 Blackbeard Has The Entire World Wrapped Around His Finger
Despite his crass and raucous demeanor, Blackbeard is surprisingly intelligent. So far, all of his goals have come to fruition without a hitch. He used Whitebeard to seize the Dark-Dark Fruit, captured Ace as a bargaining chip for the World Government, and then betrayed everyone in order to seize the Tremor-Tremor Fruit all while liberating a new crew of deadly inmates from Impel Down.
Blackbeard's sense of opportunism is why his comrades now have some of the most deadly Devil Fruits in history. He remains the single most diabolical emperor to currently plague the high seas.