Leopold Doherty

'Cabin boy and clown. How could you NOT have fun with this job?!'

0 · 438 views · located in The Jewel of the Seven Skies

a character in “Sky Pirates: Band of Misfits”, as played by Army.of.One


"Yo ho ho, a pirate's life for me!"

Back to Basics


Leopold Jefferson Doherty

He prefers to go by Leo, however many ship members just seem to call him 'Boy'



May 20th

York, North Yorkshire, England

Role on Ship:
Cabin Boy

Role in Circus:

First Impressions


Five feet four inches

One hundred five pounds

Extremely thin with no muscle definition

Hair Color:

Eye Color:
Clear, light blue

Scars or Markings:
Leo may only be a young boy, but he does sport a few scars. He has a small pink scar on his right shoulder from his first day on the flying pirate ship. When it took off, he fell backwards and scraped himself on some machinery. He affectionately calls it his 'battle scar.' He also has an irregularly shaped birthmark on the underside of his right wrist.

Brief Written Description:
Leo is, quite simply put, an adorable boy. He has extremely bright blue eyes that are always full of excitement and earnest, while his pink lips are frequently pulled up into a smile. His long, dark locks are always unruly fro his activity, and he never takes the time to style it or make it look presentable. He stands at an average five feet four inches, and weighs a thin one hundred five pounds. He'd always been a skinny boy, but since becoming a member of Annie's ship, he's grown even more so from all the activity. His skin is quite pale, even though he gets an adequate amount of sun, and it never seems to want to tan. Leo tends to dress quite plainly, since most of the time he is working or exploring the ship. His clothes are most always covered in dirt and grime, considering his love of new places and watching the machinery work in the lower deck.

Digging A Little Deeper


Quirks and Faults
+ Short attention span || Leo travels around the ship all day, delivering messages, and if anything catches his eye along the way, or he finds someone he wishes to talk to, his work will be delayed .

+ Facial expressions || Leo is a very exuberant boy, and he can make the silliest expressions randomly. Not to mention that his face is almost always an open book, his face giving away his innermost thoughts and desires.

Calling himself a pirate || Laughter || Exploring || Flying || Amalia, the sailmaker || Annie, his aunt || Being in a circus || Making games out of work || Movies || Watching machinery work || Rain || Talking to people || Dogs || Candy || Running || Cake || Clouds || Stars || Making people happy

Being treated like a baby - when he doesn't want to be || Not feeling important || Being ignored || Seclusion || Loneliness || Sadness || Talking about how his father died || Vegetables || Snow || Reading || His aunt yelling at him || Rodents || Dressing up || Bullies || Being called 'boy' || Anyone using his full name || Sitting still for too long || Fish

+ To become a famous pirate || His aunt is one of the most famous pirates in the world, and he wants to follow in her footsteps. What cooler job is there than a pirate?! He would just get to have fun all day long.

+ Having Amalia love him || From first sight, he was smitten with the red-headed beauty. And time has only strengthened his so-called love for her. He spends nights lying awake, making plans for a way to win her heart.

+ Losing Annie || Having lost his father at such a young age, Leo is extremely frightened of losing the only family he has left. He doesn't want to be alone in the world.

+ Having to be a normal boy || Leo has had anything but a normal childhood. And he thoroughly enjoys the life he lives now. He finds his life fun, and thinks of himself as special. He wouldn't know how to function if he had to go to school or work every single day.

+ Optimism || Leo is generally a happy person, and tries to see the best in everyone he meets and gets to know. Not only that, but his personality is infectious. People tend to just feel good around him. And he has the ability to make everyone laugh.

+ Agility || Leo is small, and therefore very agile and quick. He spends a majority of his days running around the ship delivering errands, which has led him to have great endurance and speed. He can generally run away from anyone chasing him, which comes in handy when he's supposed to be getting in trouble.

+ Childish || Let's face it, Leo is still only thirteen. He still has the curiosities and downfalls of being a boy. He likes making mischief, breaking (or bending, as he calls it) the rules, and generally causing just a slight bit of havoc.

+ Fear || As much as Leo likes to pretend that he is big and strong, he is still just a boy. Sometimes, he becomes afraid for seemingly no reason. And sometimes, he just wants to be held, have fingers run through his hair, and be told that everything is going to be okay.

Under My Skin


|Exuberant, Curious, Mischievous, Infectious, Boyish|

Being the youngest person on the pirate ship, Leo has to create his own fun. And he does. He loves to explore every nook and cranny of the ship, crawling into the smallest holes to see where they lead... even if he is supposed to be running errands. Sometimes he can be found sitting in the bowels of the ship, watching the machinery at work. No one knows why, and he isn't even sure himself, but he is fascinated by the way it works. Because his job is rather important - keeping all members of the ship informed and on the same page - he can't skip out too often. So he likes to make games out of his errands. Making it to the location in a record amount of time, or being sure never to step on a crack between the boards the entire way throughout the ship.

Leo is full of life and has an infectious personality that very few can ignore. His bubbly laughter can be heard throughout the entire ship, and he always makes time to say hello to everyone he passes. He keeps up with everyone, asking how they are, of if they feel better than they did yesterday. He is a people person and generally cares about what they have to say. His favorite thing, however, is making others laugh. It gives him such a good feeling, and there is nothing like it in all the world. He is very expressive, and anyone can tell what his thinking or feeling by the expression on his face. It's impossible for him to hide his innermost thoughts.

He believes the pirate life was made for him, and enjoys every single day of it. His biggest dream and aspiration is to become a famous pirate just like his aunt, Annie. Not having to attend school every single day and being able to learn at his own pace is one of the things he loves most. If for some reason he had to return to a 'normal' life, he isn't sure he'd be able to. Annie is the most important person in his life, and the only family he has left. His biggest fear is somehow losing her, and then he'd be truly alone. Sometimes, when thoughts like that get into his head, he just wants to be treated like a kid. He'll go to Annie, wanting her to just tuck him in and read a bedtime story, running her hands through his hair like his father always did.

Diving Into The Past



Little Leopold Doherty was born on a chilly May morning to Edward Doherty III and Marie Doherty. Later on, he learned that he was born only one day after his aunt's own birthday. He doesn't remember much before he was two years old, so thankfully he doesn't recall the fighting. His parents split only days after his second birthday. His father never really explained what had happened, but his mom ended up giving Leo's father full custody, and he never saw her again. Of course, Leo didn't have too much to complain about. He was born into a family of great wealth that loved him and gave him pretty much anything he desired. He honestly never yearned for a mother, having his dad be so caring, and his grandparents always present.

This all caused him to be a very happy child, and at school he was very popular. Everyone wanted to be in his presence, and that only made him happier. Of course, the person that made him happiest was his father. They enjoyed working on projects around the house together, even when Leo was as small as six. This taught Leo the benefit of hard work, and that everything can't be handed to you in life, money or not. His favorite time was when he was tucked into bed, and his dad would tell him stories. They were always of a great pirate named Annie, who his dad told him was actually his aunt. Of course, Leo never truly believed what he was saying was true. How could his rich, posh family possibly have a pirate in the family? His father never wavered on the facts, however, and Leo just let it go on.

Leo's life was changed dramatically when he was eleven. His father was hit by a car and killed instantly on the scene. Leo was beyond devastated. The only person that truly seemed to understand him was gone. His grandparents took over taking care of him, but it just wasn't the same. He lost everything that identified him as Leo. Sadness enveloped him, and depression was common at only eleven. Bullies began to harass him at school, since he was no longer popular. He just felt stuck, and didn't know which way to turn.

That was until Annie walked into his life. She just appeared on the doorstep one afternoon, and she was just as his father had described. They'd never met, yet Leo wrapped his arms around her immediately. She had come to take him away, she explained. Of course, his grandparents would have none of it, and forbid that his life be ruined by his aunt. She ignored all of their protests anyway, whisking him away one evening. He didn't miss his old life at all, and that action was the only thing that could have snapped Leo out of his sadness. He began to become himself again, and even told Annie the adventures his father had told him every night, even though his aunt had experienced them first hand.

The best part came when he got to finally board a flying ship for the first time. It was like nothing he could have ever dreamed. And the feeling of being in the sky, wind blowing through his hair, free as a bird; that was the best feeling. His aunt had explained his role on the ship, to be a cabin boy. His main purpose was to follow Annie's directions. He didn't mind working so closely with his aunt. He also got to deliver messages from others to his Aunt, and this allowed him to really get to know the entire crew. They were all so fascinating, having such different and unique back stories.

The one person he was most pleased to meet was Amalia. He still remembers the first time he ever saw her. She walked onto the ship, red locks down and blowing in the breeze. Her cheeks were slightly rosy, and she just looked radiant. Leo almost became weak kneed at the sight of her. Everyone had gone forward to introduce themselves, and Leo could barely even manage a hello. He awkwardly shook her hand before fleeing, embarrassed at his display. Over time he became more comfortable with her, but his love only grew stronger. Sure, she was seven years older, but to him that didn't matter. All he wanted was her. And he would find a way.

How often do you get online?: Everyday
How often can we expect you to be able to post?: Every couple days
Password: Buried Treasure

So begins...

Leopold Doherty's Story

Characters Present

Character Portrait: Annie Doherty Character Portrait: Zizi Character Portrait: Amalia Winchester Character Portrait: Blayke Crandall Character Portrait: Leopold Doherty

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It was a rather cool morning for summer, yet still the wind felt good. It would most certainly warm up, the blistering heat hitting mid-day. And he would mostly be stuck in the bowels of the ship, where the heat seemed to hang in mid-air, almost suffocating. So Leo closed his eyes and let the wind blow through his hair, a small smile appearing on his face. This life was like nothing he could have ever imagined for himself. His heart began to beat faster just at the thought. Every kid dreamt of being a pirate, and yet he got to BE one. His home was a flying pirate ship, and he got to be a clown in a circus. He was living a childhood dream. Sure, he missed his dad. There wasn't a day that went by where his father wouldn't pop into his head at hearing a certain phrase or seeing something that triggered a memory. And yet, he could just imagine his father looking down, happy his son was living out his dreams. Even if he was a pirate that helped steal from the rich.

Of course, during all the heists, he had to stay on the ship with a babysitter. Leo huffed out a breath of frustration - knowing that his aunt was just trying to look out for him - but still, he wanted that adventure. Even if she would let him go just once. But, she always refused. And, being the 'good' little boy he was, he obliged. When he snapped out of his thoughts, the sun was higher in the sky than he expected. Panic began to overcome him. He was going to be late. And Annie hated it when he was late. Immediately he took off, running across the deck, his shoes clip-clopping against the hard wood. There weren't very many people up and about yet, but the few that were received a wave and smile from the young boy. He may be running behind, but he certainly wasn't going to be mean!

Suddenly, a crew member stepped out in his path, and the pair almost collided. Leo expertly slid his feet out in front of him, his bum sliding on the dewy deck of the ship, right between the legs of the man. The man gave out a yell as Leo stood up and kept running, but he looked back with the biggest grin on his face. Annie's cabin was towards the back of the ship, located on the highest level. Leo's room was right next door, though considerably smaller. Of course, she was the captain. She got the best spoils of the group. As he approached the door leading down below deck, he slowed his pace, but only slightly. He threw the door open, not bothering to close it behind him, and leaped down the staircase, landing at the bottom with cat-like grace. He took off at a sprint once more, dodging between crew members who had finally woken up and were reporting to their duties.

When he reached her door, he came to an abrupt halt, then opened it slowly, peeking his head inside. Annie was sitting at her desk, papers strewn out before her. She picked one up, then another, hand running through her hair. After a moment, Leo slid inside, closing the door softly behind him. "Auntie!" he exclaimed, holding his hands out in a big gesture.

Annie lifted her head, then swiveled her chair around to greet him. Her face gave away nothing. "You're late," she said simply.

"Yeah... he said, holding the syllable out for longer than he should. "But not too late!"

Annie couldn't hold a straight face any longer, and a smile appeared, turning her face set in stone to one as bright as a ray of sunshine. "You silly little boy," she said, standing up and approaching him, wrapping her arms around him lovingly. She gave him a good squeeze for a few seconds before releasing her hold on him. "I have a job for you already," she said, walking back over to the table to consult the pieces of paper once more. "I need you to go and fetch Zizi, please. And be polite. I just need to ask her one more time about this choice of location..." He noted a bit of worry creeping into her voice. Leo's aunt was always very honest about her plans and ideas. She didn't hide anything from him. After all, he was thirteen years old. He could handle anything she had to say.

"You got it!" His voice was exuberant and joyful, his teeth showing through his smile. He ran to the door, opened it, then turned back to face is aunt. "Captain!" he shouted, then gave her a goofy salute, before exiting her cabin. He took off at a run once more, only stopping at an intersection to wonder which way he should go. Where exactly would Zizi be this early in the morning? Guessing, he took a right turn, making his way to the inner part of the ship. And, coincidentally, the direction of Amalia's cabin. Perhaps he would conveniently run into her on his way...

Meanwhile, Annie was bent over her table, staring at the maps. Zizi had given her clear direction on their first target. A rather wealthy young gentleman in the field of politics, who wished to put the poor down even more. Moving them away from the inner city, pushing the slums farther from resources. She slammed a fist down on the table. Her only plan had been one of seduction. Distract him long enough to drain his wealth dry, and then take off back into the night. Yet, that plan didn't seem solid enough to her. Too much could go wrong. And this was their first operation as a team. If they failed, it wouldn't bode well with most of her crew, she had to guess. And so she had called on Zizi, who she hoped would have some insight into this whole predicament. Annie knew she worried too much, but this was her crews safety on the line, and failure couldn't be an option.

She considered calling on Blayke. She could certainly use him to destress. Yet, she figured he was busy, and it was early. Not to mention, if Leo was efficient, Zizi would be coming sooner rather than later. And if Blayke was present, that would be an awkward conversation to have.

Characters Present

Character Portrait: Lysander Islinger Character Portrait: Francis Savage Character Portrait: Emilia Knox Character Portrait: Katarina Zarubin Character Portrait: Amalia Winchester Character Portrait: Blayke Crandall Character Portrait: Leopold Doherty

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Curled up, much like a cat, in the hammock the small sail maker began to stir. No movement coming from her until her grey eyes began to flutter open, yet they closed as soon as they were open. Soon more movement accompanied, Amalia slowly uncurled herself from her human ball. She stretched, her muscles tensing as she gave a small satisfied sigh, finally opening her eyes all the way. She scanned her surroundings, feeling a bit lost at first, causing her to look very kid like. Once she got her bearings she sat up, swinging her legs over to where they hung off the hammock, no intent on touching the ground quiet yet.

Amalia had made it a habit of being one of the last to awake on the ship. She stretched once more, her feet reaching for the floor but not finding it. She glanced around, running a hand through her wild red hair. Hopping off her hammock as she went over to a pile of clothes, Amalia wasn't one to keep things organized. Throwing off her clothes she was in carelessly as she slid on a loose-fitting blue shirt, rolling up the sleeves and then shimmied into a pair of pants, which fit tightly, yet she rolled them up to mid-calf. Running a hand through her hair yet again, trying to decide if she should go with or without shoes.

Though she would regret her decision she made her way out of her cabin, silently and barefooted.

The sailmaker was going towards the large sail out on the deck, just for routine inspections. As she made her way towards the upper deck, she repeated a list of things she needed to do - out loud.

"Check the sails, try to make Lysander's hammock longer, fix a few of the circus flags, double check Kat and Blayke's silks, and fix that hole in your pants.." (The first was a given, the second was due to the height the man possessed, the third was due to the show they were putting on, fourth was for good measures, and last is a story Amalia would rather not revisit) She repeated that, over and over to herself quietly a good three times before she reached the top deck. Out of instincts she stopped, silently observing her surroundings. She recognized the pilot right off, Emilia, Amalia found the blonde a bit intimidating. The things she could do with knives was incredible, yet scary. Amalia was just glad they were on the same side, plus she found it amusing that their names were similar. Then her eyes were on Francis, recognizing the hang over immediately, she gave a small grin. "Been there, done that." She mused, quietly to herself, with a small giggle.

Then she heard the familiar clip-clopping of shoes on the deck, "Good morning, Leo!" She called, with a small wave and a large grin. She then headed towards the sails so to began marking things off her to-do list. "You better do what you're told first..don't want you gettin' in trouble." Amalia's voice was soaked in her southern accent as she gave a sly grin towards the boy. "I'll be right here when you get back." She promised before he could object.

With her attention now on the sails, Amalia smiled into the warm sunlight. She kept her mind on anything but the heist that would be occurring that night. She had no desire to be worried.

Characters Present

Character Portrait: Annie Doherty Character Portrait: Lysander Islinger Character Portrait: Leopold Doherty Character Portrait: Oluchi Yeboah

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    She dreamed of days where she worried more, and fussed over the small things that didn't concern life and death. Horizontal though she was, pelts brushing her cheek, it seemed she could not have more of a care in the world. She was not dressed, not made up, and feeling altogether contentedly reluctant. Selima had no plans of getting out of her bedclothes for a while, however long she'd been awake. Someone was coming to fetch her, after all, and it would be best if she stayed still.

    "Mm..." she arched her neck, cracking a chain or two along her spinal cord as her eyes fluttered shut. Only blackness and the after image of the window's light greeted her. Groaning, Zizi rolled upright. Annie would be disappointed that she didn't have more specific news--specific, specific, the girl always wanted it specific and Zizi couldn't blame her--but the lack of ill will shall have to do. The politician was careless, she knew that much; one would have to be to decide to swindle money from the less well-to-do populace. What danger there would be would come from what lies around him. Her chin perked upwards, and she traded stares with the broken clock on the wall before her. Jutting from the ajar little door, the little bird on it's plank had its beak mostly shut. The minute hand below twitched from time to time. Perhaps... her Boatswain would be willing to give it a fine tuning.

    Unfurling, her feet came flat against the floor, and her toes wriggled as the cold crawled up her legs. Slippers, slippers. She found them under her vanity, adjusted her tri-fold mirror, and got to work adding some color to her cheeks. "Yes, you're already beautiful," she told her reflection, "but we need to hide some discerning details." Or enhance them. Depending on the day and the crowd, Selima was better off looking older and haggard. It would not be today; richer audiences expected their fortunes to be clean and not laden with cobwebs and the juices of a boiling cauldron.

    Still in naught but a linen dress and cozy footwear, she dragged a shawl about her shoulders and stepped out of her room. Leopold was late, and she was steadily growing hungry. A drift down a hallway and half a flight of stairs later, she had pancakes set before her. Pancakes. With chocolate in them and a merciful coating of jam--"Mercy me, Oluchi. Oluchi, darling. Pulling out all the stops today, are we?" Crewmembers behind her were chowing down, and pretty happy about it from what she could hear. Oh, she knew adopting this one into the crew would be the best thing that would happen to them, she knew from the start. "Oluchi," she called again, balancing a plate of food and utensils on her hip by the time she found him. She leaned forward conspiratorially and spoke in a giddy hush. "I've a plot, you see. There is a bloodhound puppy sniffing out my trail; what say you come with me when he finds me, bring an entire stack these scrumptious things, and make sure madame captain actually feeds herself this fine morning? It will be so horribly unprofessional, I could die."

    She squawked out a curt laugh. Then her trouble-making grin seeped back, fading into a more demure smile with wide-eyed blinking. "And I'll give you my love if you've tea to spare."