Luffy had been told many times, emphatically and at length, that he was a dumbass. While it wasn't something he was proud of, it also wasn't something he was ashamed of. Being stupid just meant that you had to leave the thinking to your smarter friends.
And offloading his thinking to other people was something he was always glad to do. The time loop situation had forced him to do more thinking than he liked, but he still relied heavily on his friends to figure stuff out.
"So this situation with the Trump Pirates keeps happening, but El Drago isn't showing up anymore?" Nami summarized thoughtfully.
"Sounds like whatever is causing the time loops intends to back off after you completely master the challenge." Usopp pondered.
"Makes sense." Zoro grunted, and to him it did. Why keep repeating the same thing over and over if it wasn't challenging anymore?
"I want to know more about this sexy lady that future me wanted in the crew." Sanji contributed, puffing on his cigarette and acting cool. "What are her sizes?"
"About this." Luffy held a palm slightly above his own head.
"I meant her three sizes, her golden ratio." Sanji made an hourglass shape with his hands, his composure beginning to crack as his perverted nature began to take over.
"Why would she have three sizes?" Luffy asked, confused and a little annoyed. "And if you want to know about gold, then ask Nami."
"Yes, Sanji-kun, why don't you ask me about her golden ratio?" Nami smiled sweetly.
Like any man, Sanji felt the hand of death upon him at her tone. A sensible man would have backpedaled and made excuses.
Sanji was not a sensible man.
Making kissy faces at the navigator, he began to noodle about in delight. "Ohhhh, Nami-chwan! Are you jealous? Fear not, your gallant knight has enough love for all the beautiful ladies of the sea!"
"Oi, maybe you could bring this woman onto the crew for just one loop and pump her for information about the Trump Pirates?" Usopp suggested, staunchly ignoring the war crimes Nami was committing on Sanji in the background. He was especially ignoring Sanji's mixed cries of pain and pleasure.
"Just take her prisoner and interrogate her." Zoro said sharply. "We are not making nakama under false pretenses."
Luffy's distasteful expression cleared up at his first mate's words. Zoro understood. They'd never taken anyone prisoner before, but it was much better than offering Honey Queen a place in the crew just to use her. Usopp's idea about questioning her had merit otherwise.
"Does it have to be the liquid girl?" He asked, scratching his cheek. "We could take any of them…"
"NO!" Sanji screamed from the floor. "It definitely has to be the sexy lady! She sounds like the brains of the operation!"
"From the way Luffy described these Trump Pirates, you're probably right, but I can't help but think that it's not your main concern." Usopp deadpanned.
"Love Cook." Zoro scoffed.
XXXXX
Having already successfully done this song and dance before, the assault on Clockwork Island went like clockwork.
Puns! Quips! Jokes!
In any case, the Trump Pirates were thoroughly defeated. The only difference was that when Luffy chomped Honey Queen, they had a big jar ready. When the fluid woman forced her way out of his sinuses, it was right into captivity. So stuffed into a container much smaller than her human body, she wasn't able to transform back, and her Logia form allowed her no physical strength.
As the Straw Hats sailed away from Clockwork island, the interrogation began.
"Tell us all about the Trump Pirates." Luffy made an extremely vague demand.
"Why? You already killed them." Honey Queen sulked, no trace of her previous sensually teasing cadence in her voice. Granted, it was hard to be sexy when you were a mass of fluid stuffed into a jar.
"Because we'll kill you too if you don't." Zoro threatened mercilessly.
"Don't threaten a lady!" Sanji roared in outrage, trying to kick him.
"And what will happen to me if I do?" Honey Queen asked as the swordsman and chef devolved into one of their frequent fights. "Is your captain going to keep me as a bedwarmer? Or am I to be passed around as entertainment for your entire crew?"
"But I sleep in a hammock?" Luffy tilted his head in confusion.
"Oi, Luffy, that's not what she meant." Usopp tried to explain, supremely awkward thanks to the insinuation.
"Eh? What did she mean, then?"
And that was when Usopp realized that he had blundered.
"We'll just let you go." Nami took over, seeing that all the menfolk were going to be completely useless for one reason or another.
"Just like that?" Honey Queen was extremely skeptical.
"Just like that." Nami confirmed. "We don't really care about you, we just want to know about the Trump Pirates."
"But why?" Honey Queen pressed, confused. "The Trump Pirates are gone, thanks to you."
"I'm stuck in a time loop and I need to beat them faster." Luffy revealed.
"Why are you telling things to the prisoner, that's not how interrogations are supposed to work!" Usopp karate chopped him in the head.
"Is that right?" Honey Queen purred. While the statement sounded ridiculous, they really had no reason to lie to her and their captain didn't strike her as the cunning sort. Even if he was simply insane, it still meant that he and his crew believed it. "In that case, then no, I don't think I'll be telling you anything."
They might not be as close as the Straw Hats, but they had called themselves the Trump Siblings for a reason. If push really came to shove, they would have still turned on each other, but it hadn't and Honey Queen was spiteful enough to keep her mouth shut just to inconvenience them.
"Luffy…!" Nami growled, just glaring angrily for a few seconds. Then she slumped with a gusty sigh. "Ah, whatever. You're the one who's going to need to suffer another loop because you can't keep your mouth shut. Maybe it'll teach you something."
Of course, they still tried to incentivize Honey Queen to spill the beans, but the problem was that they really didn't have much to offer or threaten with. Even with no proof of the time loop, the blonde fluid woman still just kept on delaying until the timer ran out.
XXXXX
The next time around, Luffy was extra sulky, but they did capture Honey Queen again. This time, he just sat his special seat and stared out across the ocean as his crew did the interrogating. To be more precise, Nami and Zoro did the interrogating, playing the roles of bad cop and worse cop.
That got through to the fluid woman much better than the confused interaction of the first time and she revealed everything, seeing little point in keeping secrets since the Trump Pirates were already defeated.
The problem then was actually using the knowledge. To Nami, genius that she was, the information on fleet patrols was as simple as basic arithmetic. To Luffy, it was an incomprehensible eldritch tongue spoken by higher dimensional beings.
No matter how he tried to memorize it, the whole thing got jumbled in his head and turned useless.
And that wasn't even everything. They also extracted information on the traps, and perhaps most importantly, the operation of the elevator that would allow one to skip it all.
Needless to say, the Straw Hats ran afoul the Trump Pirates armada once again when they attempted to follow Luffy's directions. That incident necessitated a change of plans.
XXXXX
It took a frustrating few loops to figure out a proper plan to minimize the mount of time it took them to deal with the Trump Pirates. This plan also ran into some difficulties…
"THE NUMBERS ARE…?" Luffy exploded out of the barrel he had been riding in, quickly pummeling the three Alvida pirates unconscious.
"AAAAAAH!" Coby screamed in fear and fell on his ass.
"The numbers are…?" Luffy tried to remember the number for the mechanical security keypad on Clockwork island's elevator, but he had fallen asleep in the barrel. "CRAP! I FORGOT AGAIN!"
XXXXX
The next loop, Luffy stubbornly refused to fall asleep and spent the entire time repeating the numbers to himself.
"GIVE ME A PEN AND PAPER!" He roared as he exploded out of the barrel, knocking out the three Alvida pirates and grabbing Coby by the shoulders, screaming in his face.
"AAAAAH!" Coby panicked and passed out in fear.
By the time Luffy woke him up, the numbers had all gotten jumbled in his head again.
XXXXX
"Hey, do you know where I could get a pen and paper?" Luffy asked politely after he knocked out the three Alvida pirates.
"What?" Coby blinked in confusion, utterly baffled by the non-sequitor.
"Pen and paper." Luffy repeated, significantly less patiently.
Conditioned to obey at the first sign of anger, Coby snapped to attention immediately. "R-right! I think there should be some this way."
"Thank you."
A couple of weeks and several boringly well-worn adventures later, they crew was back at Clockwork Island, having once again used the services of Borodo and Akisu to evade the patrols.
"Alright, this is it." Nami said, peering at the keypad. It was some impressive-looking technology, as expected of Clockwork island.
She punched in the numbers written down on the piece of paper Luffy had handed her, pointedly ignoring how crumpled and sweat-stained it was, along with the barely legible writing.
Nothing happened.
They all looked at it for a second, then Nami woodenly turned her head to stare at the rubber man.
"Luffy, are you sure this is right?"
"I think so?" He replied uncertainly.
In truth, he'd gotten the numbers jumbled up again while repeating them to himself in the barrel, never even realizing it.
They tried waiting for one of the Trump Siblings to eventually use the elevator, but that just resulted in a chaotic mess of a battle.
XXXXX
This time, when Luffy awoke on his dinghy, the first thing he did was break off a piece of wood and use the sharp end to carve the numbers into his arm. He just couldn't trust his brain to keep them straight in his head!
That ended in another failure, as it turned out that Luffy had jumbled up the numbers before the loop even reset. He spent the remaining loop time writing the numbers into the sand of the beach with a piece of driftwood.
His original idea had been to keep carving it into his arm over and over again, but he had received a fist to the head and been informed of what a dumbass he was. There was no need to mutilate himself when writing into the sand would achieve the same thing.
XXXXX
When the door of the elevator gave off a pleasant ding and opened, Luffy fell to his knees in relief.
"YES!" He cried, glad that it was finally over. This whole time loop business had been infuriating in many ways, but to be defeated by a bunch of numbers was perhaps the worst so far.
"Get in here already!" Nami yanked him, greedy for the Diamond Clock.
As soon as he was inside, she pushed the button that would take them all the way up.
"Shitty rubber…!" Sanji ground his teeth and tried to squeeze himself towards the only female present. "I should be the one pressed up against Nami-swan!"
His maneuvering resulted in much grumbling in the tightly packed elevator. Then there was an ominous sound of groaning metal.
"Wait, what kind of carrying capacity does this thing have?" Usopp asked with a sense of dread.
It had occurred to him that the Trump Siblings only numbered five, and Bear King was far too large to fit into the elevator. There were currently seven of them squashed into it. The remaining four, although somewhat bulky in the case of Boo Jack and Skunk One, were not especially heavy.
The engineers of Clockwork Island, clever as they were, had not thought to include a weight sensor. They had, in fact, been hoping that Bear King would use the elevator and fall to his doom. No such luck, as the captain of the Trump Pirates barely ever left his castle since it was built.
The elevator's machinery gave out on the Straw Hats about halfway up to their destination, sending them falling to their doom. Not all of them were killed or seriously injured, but the loop was still a failure.
Even worse, Luffy had long since erased the combination from his mind, not caring to remember it after he'd written it down.
The Alvida of the next loop never learned why the skinny stretchy kid beat her and her crew so viciously.
XXXXX
Luffy's irritation was not improved when, on the way to the Baratie, Woonan and treasure island was mentioned.
"Why are you talking about him, we already did that stupid side adventure!" He whined.
"You mean we found Woonan's gold?!" Nami was instantly all over the implication.
"There is no gold anymore, he gave it all back." Luffy grumped.
"That idiot, how dare he give away my gold?!" She screeched.
When a familiar trio of thieves tried to rob them, they got pummeled quite severely. And when El Drago tried to practice his Devil Fruit near them, he got pummeled even worse. Thus was the side adventure averted before it could even get started.
XXXXX
After a couple loops more, the Straw Hats were finally back at the elevator with the correct combination.
This time, there would be no stupid deaths!
Luffy, Zoro, and Sanji were the only ones that went up, not wanting to risk overburdening the elevator.
The gentle rattle of metal announced their arrival at the top of Trump Castle.
To their surprise, there were only three of the Trump Siblings there. Unbeknownst to them, Borodo's evasive maneuvers and their lack of encounter with Honey Queen had allowed them to beat the patrolling armada to the island.
"Roronoa Zoro?!" Pin Joker exclaimed in shocked anger, staring at the green-haired swordsman.
"… Do I know you?" Zoro asked in confusion.
"How can you not remember?! You were the one who gave me this scar!" Pin Joker shouted, even more angry.
"I don't remember weaklings." Zoro dismissed him.
I'll make you remember!" Pin Joker roared, brandishing his sword. "Time for some 'back pay'."
"You mean payback?"
Being corrected didn't help his temper any, and he launched himself into a thrust with his rapier.
Everyone else ignored the two sword users as they started fighting.
"Who are you?!" Bear King demanded irritably.
"Monkey D. Luffy, future Pirate King. I'm here to kick your ass." Luffy told him blandly.
"Future Pirate King?!" Bear King and Skunk One guffawed derisively. "With the power of my King Cannon, I will be the Pirate King."
"You're not even a real pirate." The rubber man dismissed him.
That was about all it took to provoke Bear King into a fight.
A very one-sided fight, and not in the way he expected. Bear King's Stone Stone Fruit gave him more defensive power than just about anyone in the East Blue could deal with, but Luffy had faced off against vastly more dangerous opponents.
Sanji had it even easier. Luffy had already warned everyone about Skunk One's gas attacks, so the chef never even let him get a chance to use it. A quick rush and a kick to the face was all it took.
"Alright, let's go!" Luffy ordered once all three of the Trump Siblings were defeated. He was eager to get back on track and didn't want to lose any more time.
"But what about the sexy lady you mentioned?!" Sanji protested.
"Leave the rest to the Marines." Zoro grunted, disappointed by how weak Pin Joker had been. "This whole thing has been a disappointment."
Sanji agreed, but not for the same reasons. He had really wanted to see the sexy lady that took her clothes off a lot according to Luffy.
XXXXX
The Straw Hats had tried to rush their voyage as much as possible to make up for the time delay of the Clockwork Island detour.
Luffy waited anxiously on the figurehead of the Going Merry as they sailed down Reverse Mountain, hoping that they were not too late.
"Is that a mountain?" Usopp asked, squinting into the distance.
"LABOON!" Luffy cheered, not just because he was glad to see their whale friend again, but also because this meant that they were on time.
XXXXX
OMAKE – The Peanut Gallery
Commodore James Norrington intended to arrest all of these pirates, see them hanged, and then marry Elizabeth Swann.
"You are all under arrest." He declared once he had the crew of the Black Pearl, both past and present, cornered.
He did find it odd that they allowed themselves to be cornered so easily, but aside from being extra careful of any shenanigans from Jack Sparrow, was not going to look a gift horse in the mouth. That said pirate was just grinning at him, along with the rest of the crew, sent a shiver of worry up his spine.
Still, he had them surrounded, disarmed, and he was given to understand that they were no longer cursed to become unkillable abominations. It should be fine.
It was not fine.
"No." The skinny boy in the Straw Hat said blandly, picking his nose.
"And who are you?" The commodore demanded.
"Monkey D. Luffy, future Pirate King." The boy replied insolently.
"Then you are under arrest, in the name of King and Country." James insisted.
"You're too weak to arrest me."
Well, that kind of declaration go hardly be allowed to pass unchallenged.
"I think that the commodore may have made a slight… miscalculation." Murtogg, Royal Marine under the command of James Norrington, said painfully where he had fallen.
"That does appear to be the case." Mullroy, also a Royal Marine under the command of James Norrington, agreed just as painfully.
"Don't feel too bad about it, we all made that miscalculation." Pintel commiserated.
"Aye, got the tar beaten out of us by Captain Luffy we did." Ragetti nodded. "Good thing we was still immortal at the time."
"Where did you even find this man?" Murtogg asked.
"And what is he?" Mullroy added.
"Jack Sparrow and Will Turner over there say they found 'im in Tortuga, eating the place out of house and home." Pintel offered. "Can find all sorts in Tortuga."
"And 'e says that e's a rubber man."
There was a moment of silence between the four, punctuated only by the continued beating inflicted upon the Royal Navy.
"What the devil is rubber?!" Murtogg demanded.
"No idea. Somethin' stretchy, I reckon." Pintel shrugged.
"Captain said he ate a Devil Fruit that gave 'im 'is powers." Ragetti supplemented.
"The Devil grows fruit and you get powers for eating them?" Mullroy wondered. "What, do you have to go to Hell and break into the Devil's private orchard to steal them?"
"I asked that, too!" Ragetti was far too happy over the fact that someone else had the same question. "The Captain did say that 'e's been to Hell, but that there were no orchards there, only pirates, Marines, and crossdressers."
"Why would Marines get sent to Hell?!" Murtogg demanded. "We work hard to keep good folk safe from pirates."
"Maybe the standards for getting into Heaven are too high?" Ragetti shrugged. "I mean, if we're all going to Hell anyway, then we might as well do whatever we want, right?"
"He makes a fair point." Mullroy conceded. "If we're going to Hell whether we are Marines or pirates, then the pirates life does seem to have more perks."
"But what if we quit the Marines and don't become pirates?" Murtogg pondered. "Would we be spared from going to Hell? And speaking of, what does God have against crossdressers specifically?"
All four of them went silent as they pondered this mystery.
"I heard that the men in Rome wore dresses." Pintel offered. "Maybe 'e's still holding a grudge over them killing his son?"
"But didn't Jesus ask God to forgive them?" Ragetti asked. "That's what the priest used to say."
"That don't mean God actually did, ya idjit!" Pintel smacked him over the back of the head. "I knew your pa and 'e was a stubborn shite that never listened to anyone but 'imself. And didn't God drown the world once because it weren't to his liking?"
"You know, the man makes a fair point." Murtogg said with a thoughtful frown. "I know that if my son was killed by a bunch of men in dresses, I'd not be inclined to forgive them anything at all. Could it be that Christ was actually crucified by the Roman equivalent of pirates and Marines, wearing dresses?"
"You don't have a son, though." Mullroy pointed out.
"If I did have a son!" Murtogg snapped at him. "It's a hypothetical."
Nearby, Elizabeth Swann, as the most educated person present, could only despair at the increasingly more ludicrous theories the foursome of idiots was coming up with.