As it turns out, the twins ended up smuggling the…erm…smuggler back into the Room of Requirement at first light, so as to avoid the teachers and Umbridge. They left him there for days and days. Jack lost count, as for about half the time he was dead drunk, so he could hardly be called upon to remember how long he'd been there. He only knew two things: one, the rum was NOT gone, and two, the rum tasted very good. Beyond that, his brain felt too overworked to think about too much else.
Jack was in another one of his deep, drunken slumbers when the Weasley twins burst into the room, panting heavily and looking thoroughly excited.
"Jack, wake up! We have major mayhem to cause, and only a short time to cause it!" Fred snapped, looking around for some way to sober the pirate up. A jug of water just happened to be sitting next to Jack's hammock. The twins glanced at it, then at each other, and then nodded. George lifted the jug and dumped its contents over Jack's head. Icy water splashed over the pirate's face.
"Bloody hell! I'm up!" Jack sputtered as he spat out water and flayed around. He managed to flip himself out of the hammock, landing on the floor. Both twins took an apprehensive step back.
"Oh, aye, bloody brilliant idea, lads, waking a drunken pirate…" Jack coughed as he pulled himself to his feet and glared at them. Fred stared at him.
"Did you drink all that rum?" he asked. Captain Sparrow blinked and gave the ten empty bottles on the floor a curious look.
"Oh yeah…Must've. But I'm sober now, savvy?"
"Right…savvy…" George said slowly, "Well, c'mon, we've more mischief to manage before the day's out…"
When the twins said "major mayhem", Jack had not envisioned setting up a magical swamp in the east wing. Fred and George had a good chuckle when they saw the pirate's face.
"It's not that bad," insisted George.
"Yeah, we could have made it a twenty meter deep river," added Fred thoughtfully. They had no more time to talk, because just then the bell rang. It seemed students came pouring into the corridor by the hundreds. A lean, haughty looking boy with white blonde hair pushed his way through the crowd that had gathered around the swap.
"What's all this -," he snapped, but broke off when he saw the Weasley twins standing transfixed on the other side of the marsh. His pale face twisted into a sneer.
"The headmistress will want a word with you, blood traitors!" he jeered, sweeping off back up the hall.
"Damn," growled Fred as he started backing down the stairs.
"We weren't expecting him to show up right away…" mused George as he followed his brother down the steps. Jack glanced between them and the throng of students hovering by the bog. One of them suddenly tripped, crashed into another student, and toppled into the swamp. The boy he had bumped into slipped on the slimy substance that had splashed onto the stone floor and followed him into the muck. Jack chuckled nervously and ran after the twins.
"AHA! I've got you!" snarled a new voice from behind them. Filch had appeared at the base of the stairs, and Fred Weasley had backed into him. The caretaker grabbed the twin's arm in a death grip.
"HEADMISTRESS! I CAUGHT ONE!" he hollered over his shoulder. George and Jack froze. Fred struggled against Filch.
"Run!" he yelled at his horrified twin and the pirate. Neither moved.
"CHARGE!" whooped Jack randomly. He jumped the last three steps and collided with Filch, who was knocked over. Fred scrambled away from him as the janitor released his hold on the boy's arm.
"Thanks, now let's get the bloody hell away from here!"
"Right you are!"
"Aye!"
After being chased by Filch, Umbridge, and the Inquisitorial Squad, the Weasley twins and Jack wound up in the Entrance Hall. They were cornered. Students, teachers, ghosts, and very happy looking Inquisitorial Squad members surrounded them. Peeves the poltergeist, whom the twins had told Jack about, floated over the scene. Umbridge was at the head of the staircase and smiling broadly.
"So!" she said smugly, "So…you think it amusing to turn a school corridor into a swamp, do you?" Fred glared at her defiantly.
"Pretty amusing, yeah," he said boldly. Jack looked around, wondering how best to handle the situation and come out without injury. Filch joined Umbridge and muttered something the pirate didn't hear, but it couldn't have been good because Filch was grinning. Umbridge smirked at the three of them.
"You three," she said triumphantly, "are about to learn what happens to wrongdoers in my school." Fred continued to glare at her, but a soft smile appeared on his face.
"You know what? I don't think we are. George," he added, glancing at his brother, "I think we've outgrown full-time education." George nodded vehemently.
"Yeah I've been feeling that way myself," he agreed airily.
"Time to test our talents in the real world, d'you reckon," inquired Fred.
"Definitely." Jack suddenly realized what they meant.
"Oi -!"
"Accio Brooms!" A tumultuous racket filled the room as two brooms sped towards the twins – one was dragging a chain. They stopped in front of the twins.
"We won't be seeing you," Fred assured Umbridge as he mounted his broom. Jack tried to get a word in edgewise.
"Oi, lads -?"
"Yeah, don't bother to keep in touch," George put in as he climbed onto his own broomstick.
"Lads?"
"If anyone fancies buying a Portable swamp, as demonstrated above," said Fred loudly, ignoring Jack, "come to number ninety-three, Diagon Alley – Weasley's Wizard Wheezes, our new premises!"
"OI!"
"Special discounts to Hogwarts students who swear they're going to use our products to get rid of this old bat!" George ended, pointing to Umbridge.
"STOP THEM!" screamed the disgruntled headmistress in question. The twins kicked off from the ground and flew into the air. Fred paused and looked at the orange ghost floating on the other side of the hall.
"Give her hell from us, Peeves."
And the ghost in question took off his hat and saluted the twins as they sped out of the hall, applause and cheers following them into the sunset.
When the clapping had ceased, Umbridge rounded on Jack, who had been whooping and rooting for the twins.
"So you are the one who helped the Weasleys!" she snarled. Jack gave his nervous smile and started backing up.
"I was nothing more than an almost innocent bystander!" he assured the furious headmistress.
"SIEZE HIM!" Jack, in true pirate form, drew his sword…and bravely ran away up the stairs and towards the Vanishing Cabinet. The Inquisitorial Squad was hot on his heels, but skidded to a halt when he stepped into the open cabinet door.
"Good-bye, toadie!" he said with a grin to Umbridge, "This is the day you will always remember as the day you almost -." The door was blasted shut by a spell, and Jack found himself back in the fishy-smelling belly of the Kraken.
"Bugger."