Hello everyone! So, this is my first ever fanfiction on this site, though I've written a few things before, and I'm excited! This story was inspired by the recent release of the new sequel Tales of Monkey Island and the re-release of both Secret of Monkey Island and the upcoming LeChuck's Revenge.

This story was designed to basically explore just a snippet of Guybrush's past and hopefully answer some questions about how he became so... Guybrush-y. I suppose it's a bit predictable at times, and it's not really the best thing I've ever written, but I think it's a pretty good story nonetheless. Enoy!

Every time you read and don't review, LeChuck kills an innocent pirate. So please R&R for me!

Ruth turned her face upwards a little bit to better catch the light breeze that was gracing Pillage Island that afternoon. She was leaning against the railing of their island's only dock, enjoying the pleasant weather. She slowly pulled the gold locket she was wearing off and turned it over in her fingers.

"Hey mom?"

Ruth nearly jumped out of her skin at the casual greeting. "Huh? Don't sneak up on me like that, Myra!"

"Sorry. What's that you're looking at?" Myra gestured to the golden necklace sparkling in her mothers hands.

"This is a very special locket, sweetie. It's been passed down through several generations of women in our family. Someday, it'll be your locket, too."

"Woah." The teenage girl looked greedily at the beautiful treasure. "When do I get it?"

"When you're mature enough to take proper care of it." She answered with a smirk, shooting a sideways glance at her daughter.

"Well so-rry!" Myra retorted, throwing her arms up in defeat. "I didn't know I wasn't mature enou- yeek!" She was cut off mid-sentance by a rumbling crash that shattered the dock. The sand crumbled beneath their feet, and the railing cracked and splintered under their hands.

"Oh!" The older woman wailed as a particularly nasty lurch ripped the locket form her hands and plunged it into the icy deep water.


"Damn Guy, you're some kinda robot!" The jovial pre-teen laughed and flipped his wet, clumpy dark hair out of his eyes.

"How... *Gasp*... long?" An 11-year-old Guybrush Threepwood sputtered as he broke the surface of the water.

"I forgot to count. Really, really, inhumanely long?"

Guybrush sighed dramatically. "I'm trying to achieve something here, Skylar! How can I know if I made it five minutes if you can't keep count?"

"It was way longer than five minutes, man. How do you do that?"

"I dunno. I just can. You really think I beat five minutes?"

"I think you should go for ten!" Skylar said, his eyes suddenly wide. "Do you realize how useful that could be? To be able to stay underwater for ten minutes?"

"Yeah..." Guybrush's eyes widened to match his friends, and they sparkled with excitement.

"Guybrush!" A voice from further down the dock drifted over. "Hey, are you down here?"

"Whaddya want?" The young blonde shouted back, agitated at his sister's interruption.

Myra jogged over to him. "Just a warning: Stay away from mom. She's really steamed."

"What'd you do?" Skylar shot her a mock suspicious glance.

"Shut up." Then, to her younger brother: "She dopped some really old family heirloom into the water when the dock shook just now. Further down the beach, where the water's really deep. So, y'know, just leave her alone for a bit." She stalked off, leaving the boys alone again.

Even before Myra finished talking, Skylar was already putting two and two together in his head.

"Hey Guy, I have an idea," he stated as the pair watched the older girl walk down the shore. "Maybe you could go get that family thing, whatever it is."

Guybrush turned to him. "In the deep area? Are you nuts? It goes on forever. I don't even know if it has a bottom."

"Well, you're probably the only person on the island who could find out."

Guybrush, never one to think things through, changed his mind rather quickly. "Well, all right. It's worth a shot."

The two boys quickly discovered, however, that it was not going to be so easy. First, they had to find the exact spot Ruth had been standing when she dropped it. After some careful footprint studying, they believed they had it pinpointed. There were also other issues they hadn't counted on, like the strong currents. Any time Guybrush dove, he ended up going more sideways than down. He attempted to solve that by climbing down the rocky side of the shoreline, but that slowed him down so much that he didn't get much deeper than when he was being yanked out to sea.

Skyler was out of ideas, but Guybrush, who even at a young age had a knack for puzzle-solving, came up with one last plan.

"What if we found something really heavy, like a big rock or an old anchor, and I just grabbed onto that and let it carry me to the bottom. If it started to feel like I was going too far down, I could just let go and float back up. And that would get me down there really fast, so I could go further using less air, and it would be strong enough to resist the currents."

"Okay let's do it. I'll help you find something to sink with."

The two scoured the beach for awhile and eventually found an ancient, abandoned cannon that they managed to drag back to the edge of the shoreline.

"Okay, I'm gonna hold on tight to the cannon, then you push it into the water." Guybrush instructed.

"Okay. You ready?" Skyler asked, after his friend had wrapped his arms tightly around the nozzle and taken a few deep practice-breaths.

Guybrush nodded, looking suddenly nervous as the thought of a million things that could go wrong flooded his brain.

"I'll stand watch. If you don't come back up after five minutes, I'll go for help."

Guybrush smiled weakly. "Don't forget to count this time."

"No promises." And he gave the canon a mighty shove and sent it hurtling down towards the water.

The more time passed, the more nervous Skyler became. At two minutes, his heart started to beat faster. At three, he started to feel sick to his stomach. By four he was panicking, and paranoia was making him doubt himself. What if I was wrong before? What if it was less than five minutes? What if he's drowning already?

By the time it was four minutes and thirty seconds, Skylar was planning out how to tell Ruth he'd killed her son.

At four minutes and forty-five seconds, he realized he had to do something.

At four minutes and fifty seconds, he dove into the water.

The water was surprisingly clear, but even with full visibility Skyler couldn't see anything that even vaguely resembled an end to the bottom. It simply kept going until it vanished.

He began frantically swimming downwards, but since he didn't possess the freakish ability to hold his breath longer than anyone else, he soon had to turn back and surface for air. He swam to the edge and grabbed onto a rock, then proceeded to hyperventilate.

"Ohmygodohmygod what have I done?" Skylar panicked. Suddenly, he realized that he'd stopped counting. He forced himself to calm down. The last time he'd remembered clocking was five minutes. He knew he could hold his breath for about two minutes. So that makes it what... seven?

Seven minutes. No way.

The dark-haired boy glanced down at the water again, hopelessly. I should've known he'd be too determined to let go of that cannon if he needed to. Now he's probably dying down there somewhere.

Just as he was about to give up all hope, though, he saw a glimmer of white against the endless darkness of the deep ocean.

Guy's white shirt?

Skyler took another deep breath, which was exceptionally difficult since he'd started to cry, and dove down towards the glimmer.


Guybrush tightened his grip on the cannon as it sank lower and lower into the endless depth. In less than ten seconds he surpassed the deepest point he'd made in his previous attempts, and there was still no sign of the ocean ending anywhere. After thirty seconds of falling, he began to worry that he wouldn't make it, but his determination to succeed overpowered the fear, and he dutifully hung on as the plunge continued. After a few more seconds, the boy's head strted to ache and his ears felt like they were going to explode. He was pretty sure his eyes were watering, but it was hard to tell underwater. At one point he was almost positive he was upside-down for a few seconds.

How much further...? He wondered hopelessly.

On a whim, he looked down, and to his surprise, saw the ocean floor rapidly approaching.

I made it! He thought excitedly. For though he'd been determined to succeed, the fact that it suddenly seemed possible gave him a rush of adrenaline.

The cannon hit the floor in a swirling rush of sand and seaweed, and for several precious seconds, Guybrush had to remain still because he couldn't see. As the sand cleared, he began his search for the mysterious heirloom.

It was at that moment that he realized he didn't know what it was.

Well, he reasoned, I'll know it when I see it. Guybrush held on to pieces of rock and various seafloor plants to keep himself from floating back to the surface as he dug around.

After a few minutes of searching, the scrawny boy realized that he was running out of breath.

Damn! And I still have to get all the way back to the top!

He began to look more frantically, when a flash of gold caught his eye. He scooped up the object and examined it.

Some kind of locket. Is this it? He decided to hope that it was, and began to swim towards the surface as fast as he could. Luckily for Guybrush, humans float, so it was a quick trip. However, he was already lightheaded from the rapid pressure change, and running out of air only intensified his headache. Black spots began to dance in front of his vision, and soon he could barely focus on moving upwards.

I hope the current doesn't take me too far away... Was his last coherent thought before he drifted off.


When Guybrush awoke, he was on the beach, with three concerned-looking faces looming over him. One he recognized as Skylar, but the other two took him a longer time to register. They were both women, and both a little past middle-aged. After a few seconds, when his brain started working again, he remembered that they were Chloris and Elizabeth, two of his mom's friends, and also two of the island's resident nurses. After a few more seconds, he realized all three were talking at him. He was about to respond, when he suddenly remembered the most important thing: the locket. He began searching his pants and vest pockets.

"What's wrong dear?" Chloris was saying as she touched his arm gently.

"Locket! The locket." He mumbled. He leapt off the ground and began sifting through the sandy floor for it. "Did I drop it...?"

"Is this what you want?" Elizabeth asked, holding up a gold necklace.

"Yes! Yeah, that's it." Guybrush looked relieved.

"You were holding it when I dragged you up out of the water." Skyler told him. "Is that it?"

"I hope so." Guybrush said. "I found it at the bottom."

"the bottem of what?" Elizabeth inquired, raising an eyebrow.

"Uh... the ocean?"

"How'd you get to the bottom of the ocean?" Chloris cut in.

Guybrush and Skyler spent the next couple of minutes recapping their hairbrained scheme to the two women. The further they got into the story, the stupider it sounded to their own ears. By the end, they felt foolish for even attempting it in the first place. The nurses seemed to agree.

"Well," Guybrush offered in conclusion, "it worked, didn't it? I mean, I got the heirloom."

"That doesn't mean it was a good idea. You could have just as easily drowned. And I think you're more important to your poor mother than that necklace." Elizabeth explained wisely.

"Sorry Beth." Skyler and Guybrush apologized humbly.

"You're lucky to be alive." Chloris told him. She turned to Skyler. "How long was he down there before you fished him out?"

"Uh... eleven minutes? Ish?" Skyler offered.

"Uh-huh." They clearly didn't believe him.

"It's true!" Guybrush added eagerly. "I made it to almost ten minutes before I passed out! I was counting!"

Chloris and Beth glanced uncomfortably at each other.

"If you say so." Elizabeth finally conceded, halfheartedly.

"Guybrush! Guy, are you there? Is everything okay?" The frantic voice of Ruth cut through the lull in the conversation. She was practically sprinting down the beach to get to her son and the small congregation gathered around him.

"Hi mom! Yeah, yeah I'm fine."

"Oh, what a relief. I heard you'd nearly drowned yourself and i just about -"

"Look! Hey, look! I got it!"

"Huh?" Ruth snapped out of her rant for a moment. "Got what, dear?"

"Your locket. See?" Guybrush pushed the small gold necklace under his mothers nose.

Ruth clearly was at a loss for words. She stammered incoherently for a few seconds before finally just giving Guybrush a bone-crushing hug.

Before Skyler even had time to comment, however, a piercing cry from the town watchman echoed across the Pillage Island that made the whole group realize why the dock had shaken in the first place.


BWAHAHA! I leave you all with a cliffhanger. Well, not really, since I'm sure you can all guess what's coming. That's right, in the next chapter, I hope to delve into why Guybrush wanted so badly to be a pirate the day he washed up on the shores of Melee Island.