Tales from Manehattan Port: A Tugs and MLP:FiM Crossover

by SonicFan117DASH

Rating: teen
Tags: Cheerilee, Violence, Diamond Tiara, Slice of Life, Crossover, Alternate Universe, Thriller, Original Character, My Little Pony: Friendship is Magic, Cutie Mark Crusaders, Other, Adventure
Length: 4824

A simple crossover between MLP:FiM and a famous yet short-lived TV show from 1989.

What do you get when you get when you combine Lauren Faust’s MLP:FiM and David Mitton’s TUGS? I’m about to answer that.

Bear in mind this is my first story to post on this site, or on the Internet in general. What’s more, I dare say this is the first story on this site that will feature TUGS. That being said, if anyone spots any grammar errors of any kind, feedback will be greatly appreciated.

Published 2018-12-01 03:40:02 UTC
Last updated 2018-12-09 07:30:04 UTC

Prologue: Captain Starr

Thirty years. That’s how long it’s been. Although it still feels like only yesterday when the most memorable years in his life took hold. Time certainly flies when you’re in your prime and it goes without saying that the end approaches too quickly. Despite the past being in the past recounting it to himself has become the number one hobby to former captain, Skipper Starr.

Mr. Starr was a Pegasus Pony with navy blue fur, a pale red mane, and a simple yet shining star in the middle of a lovely oceanic sunset for a cutie mark. The old stallion was currently sitting in his living room, in front of a crackling fire burning in the fireplace, a cup of tea in his hooves, and his favorite old-fashioned jazz music softly emitting from his record player. The musical number playing at the moment featured a beautifully done saxophone solo, making Mr. Starr almost shed a tear in nostalgia. This particular number had been the one that was played at the party celebrating his promotion to the rank of “Captain.”

Starr chuckled to himself as he remembered the outcome of that party.

“My father never let me hear the end of it,” he chuckled.

However, living alone with nothing but his memories didn’t feel fulfilling enough for the old captain. The many different events and adventures he partook in his life were memorable, sure, but only for himself right now. In short, Mr. Starr felt that his memories should be shared in some way, like storytelling. That begs the question: how? Surely the ponies of Equestria these days had better things to do than listen to the old sea tales of a grounded old boat.

Mr. Starr shook his head furiously at that thought. What was he thinking?! He may be old but he was in no way worn out. His “old sea tales” were ones to remember and if the ponies of Equestria didn’t find his stories interesting then that was their problem! Still, it would be nice to recite his memories to an intrigued audience.

That’s not to say he didn’t go through them alone; far from it.

At that thought Mr. Starr looked up. Just above his fireplace was a large portrait depicting himself along with eight other ponies. He stood in the middle with four ponies either side of him. He looked a lot younger in the portrait; with the lack of a graying mane and glasses he had today, and the addition of a bright sky blue captain’s cap with a white feather. To his right was a pudgy Earth Pony with a blue cap, a more muscular Earth Pony with a navy blue cap, a well-dressed Unicorn wearing a black top hat and a monocle, and an elderly yet still athletic Earth Pony with an orange boater hat and glasses. To his left was a tall Pegasus pony with a sailor’s cap and sunglasses, a shorter, younger Earth Pony with a sky blue cap, an even younger Earth Pony with a red cap and some missing teeth, and finally a slim, crouching Pegasus wearing a pair of large goggles.

Mr. Starr gave a sad sigh. “What I wouldn’t give to see them again,” he thought. “Or, at the very least, relive them by sharing their adventures with any pony willing to listen.”

It was at that moment he heard a faint *thump* at his front door.

“Mail’s here,” he said aloud.

Mr. Starr had only resided in Ponyville for a month during his retirement and had gotten used to Miss Ditzy Doo’s antics by this point. With a grunt, he hoisted himself up and slowly walked to his front door. After opening his door, he was greeted to the sight of two cutie marks consisting of groups of bubbles.

“Good morning, Captain Starr!”

Mr. Starr glanced down and saw Ditzy’s walleyed face smiling broadly up at him. He did his best not to laugh at her choice of title, even more so at reminding her that he was retired.

“Good morning, Miss Doo. What’ve you got for me today?”

“Just the usual bills and such,” Ditzy replied as she got up and dusted herself off. “Plus a special letter.”

Mr. Starr may be retired but he still had a bit of strength left in his old bones. Aside from occasional odd jobs he payed bills for the house he lived in, as opposed to living in a retirement home. Ditzy Doo’s last statement caught Mr. Starr’s attention. “A special letter?”

“Yep.” Ditzy then reached her muzzle into her mailbag, pulled out a few envelopes then dropped them into Mr. Starr’s awaiting hoof. One of them was colored a bright pink and wrapped with a magenta ribbon. “Came in shortly before I began my run. I was told to bring it to you as quickly as I could.”

Mr. Starr paused for a moment. “If I may, who did it come from,” he asked?

“It came from Ponyville’s school teacher, Miss Cheerilee,” Ditzy Doo replied.

Mr. Starr had to do a double take on what the mailmare just told him. He had met the kind-hearted Cheerilee only once at the “Welcome To Ponyville!” party that that pink pony, Pinkie Pie if he remembered correctly, had thrown for him when he first arrived in town. He was still recovering from his near-heart attack, resulting from Pinkie’s hyperactive behavior and reality-bending traits, that he hardly interacted with the other locals. Mr. Starr made a mental note to watch his back in the future in case that pink party animal decided to pull a fast one on him again.

Back on the subject of Cheerilee, Mr. Starr was left wondering on what the cerise colored mare could want from him. After thanking Ditzy, entering his office room, and sorting through his other mail, Mr. Starr turned his attention to the colorful envelope that looked more like a party invitation. He carefully untied the ribbon and used his letter opener to cut open the envelope itself. Mr. Starr slid the folded paper out, unfolded it, and began to read the letter proper.

When he read the whole letter, Mr. Starr read it again to make sure his eyes weren’t playing tricks on him. After reading it a third time for good measure, Mr. Starr felt himself begging to smile. His smile kept growing until he was practically grinning from ear to ear.

Mr. Starr allowed himself to laugh wholeheartedly for five full minutes before calming down.

He made his way back to his living room. He made note the fire had burned itself out, but he’ll clean the ashes later. For now, Mr. Starr had a job to do. He then gazed up at the portrait again and said, “This, is where your story makes itself known to the world!”

Chapter 1: Arrangements

In a single-story house near Ponyville’s town hall, Cheerilee, teacher at Ponyville Schoolhouse, was having some serious inner turmoil.

The superintendent of Ponyville’s school district had asked her to arrange a special assignment for her students. However, this was not any “ordinary” special assignment. This assignment was to have Cheerilee’s students partake in intensive study into an historically significant subject of her choice, and then they were to write a report on how the subject made it’s mark in history and how it still influences the present day. Cheerilee’s superiors also stated it would be an absolute bonus if she were to acquire the assistance and class presentation of a pony with extensive experience and knowledge of the chosen subject.

The main issue plaguing Cheerilee was that she didn’t know what subject to chose!

Cheerilee wasn’t given a list of options or offered any suggestions as to what kind of subject her students would be interested in. If there was one thing Cheerilee specializes in, aside from teaching, it is being resourceful. 99% of every marking period in her teaching career was successful due to her finding any outside material at her disposal to provide prime examples of any current study.

Unfortunately, this time would become that last 1%, for she was lacking any outside resources, let alone a solid plan.

The last three years proved to be somewhat underwhelming for Cheerilee. Ever since Twilight Sparkle arrived she has inadvertently become somewhat of a second teacher to any pony she met. To put it bluntly, after the many adventures and world-saving escapades she and her five friends partook in, the many lessons they learn as a result of their experiences rub off on every pony, involved or not.

While this meant Ponyville as a whole, not just the foals, learned a new valuable lesson after another, this left Cheerilee in an awkward position. She was a teacher, yet she felt she wasn’t the one who was teaching, given a situation in or out of her control. That’s not to say she was jealous, Heavens no! She was rather proud that education in Ponyville got higher every other day.

Long story short, Cheerilee had run out of new things to teach for the year.

Her superiors weren’t making it easy on Cheerilee, and the lack of outside help was making it worse. She brainstormed deeply for any type of subject that could catch her student’s attention, anything to please them and the school board. Unfortunately, no matter how much she thought she always came up short. Any subject she could think of was either already covered, or reserved for the next school period.

Poor Cheerilee slumped down into her recliner with a loud sigh of frustration. She couldn’t remember the last time she became so stressed. The irony of it all was she is a professional school teacher, always prepared for the school year, yet she was literally out of ideas.

It was almost too much for Cheerilee. She almost started to cry. Her fruitless efforts were tugging at her mind like a rope painfully yanking on her tail.

Tugging…

The only few ideas of potential study subjects were all related to the city of Manehattan. Particularly Manehattan’s massive harbors, ports, and waterways.

Tugging..

The amount of work done there would take ten times the number of ponies in Ponyville to accomplish. But that’s where she always hit a mental roadblock. Her students already knew of the hustle and bustle of the big city.

Tugging.

However, if there was one example of hardworking harbor life she remembered ,it was the small but powerful vessels that make up the power behind the industries of Manehattan Port.

“Tugging,” Cheerilee murmured to herself.

The sturdy, reliable, versatile crafts that are the-

“TUGBOATS!!!”

Cheerilee had done it, she found the study subject she needed! Oh, why didn’t she think of this before? Doesn’t matter now; she had work to do. Only eight weeks of the school year was left. So much to do, so little time!

(Two hours later…)

After consulting with her superiors at the Ponyville School District building, Cheerilee was given approval to carry on with her class study of the tugboat. Cheerilee then retreated back to her house to write down notes on how to organize her study session.

She couldn’t believe she didn’t think about this earlier. The tugboat was perhaps one of the most historically significant vehicles in the history of big city ports and harbors around the world! They may be small but the tugboat was designed to push and pull large ships or river barges much, much bigger than them. Their simplicity has made them easy to maintain and mass produced to support contractors and businesses that use the waterways all across Equestria.

“Well,” Cheerilee thought, “that settles it. I finally have my most needed subject to educate my little ponies. I can visit the castle library for research, organize a few hoof-written assignments, and a final quiz.”

Then Cheerilee paused her writing for a moment. There was something she was still missing.

“A class presentation of a pony with extensive experience on tugboats,” Cheerilee reminded herself. “Where in Equestria can I find a pony with such knowledge?” She knew she couldn’t ask one tugboat pilot to come all the way from Manehattan on short notice. They were always too busy with ever-increasing harbor work to be away for long periods of time.

“Perhaps,” Cheerilee thought, “I could ask one who is retired?” Old ponies from Ponyville’s Retirement Home have helped her teach in the past. However, of all the times she visited the retirement home she couldn’t recall meeting, or hearing of, any pony there who once worked in the maritime business. This got Cheerilee worried.

Before Cheerilee went into another state of near-panic, she suddenly remembered some pony from a month ago who perfectly matched what she needed.

It was another one of Pinkie Pie’s welcome parties for a new resident to Ponyville. Cheerilee couldn’t remember his full name, but she knew his last name was “Starr.” At first glance, he seemed to have recently entered retirement and had come to Ponyville to live it out. Instead of moving into the Ponyville Retirement Home, as one might have thought he would, he purchased a small but roomy single-story house close by Ponyville’s windmill.

Anyway, Cheerilee tried to introduce herself to Mr. Starr, but the poor old stallion was still recovering from his shock from meeting Pinkie Pie. Cheerilee honestly couldn’t blame Mr. Starr for that; Pinkie Pie and her behavior can make any pony’s head spin. All she could get from Mr. Starr was he used to work in Manehattan Port thirty years ago. Judging from the old captain’s cap he was wearing, Cheerilee theorized he used to be a captain of some sort. The party was short-lived before Mr. Starr excused himself from Sugar Cube Corner to retreat to his new home.

At that thought, Cheerilee set aside her notes and brought out a new sheet of paper. She dipped her quill in the inkwell and began to write.

Dear Mr. Starr,

My name is Cheerilee. I am the Ponyville Schoolhouses’ teacher and am in need of your assistance. You see, I have need of a pony who has profound knowledge on a certain subject I’m planning for my students. The subject just so happens to be tugboats. Given their historical significance and vast versatility it seems to be an ideal lesson to close this school year. An additional pony presentation would be greatly appreciated. I don’t wish to sound desperate but you are the only pony I can think of who can help me in this manner on such short notice. To be perfectly honest, I’m not even sure if you could provide any information on tugboats. I assumed you would since you were wearing a captain’s cap when we met. Like I said, I am rather desperate and any pony with experience in the maritime business is better than nothing. If you agree to present yourself, just make your way to the schoolhouse this Sunday morning and we can work out the details. I realize this is sudden and you don’t have to do this, but your efforts will be handsomely rewarded.

Sincerely, Cheerilee.

Once Cheerilee finished writing the letter, she put the quill away and folded the paper. She then put the folded letter into an empty pink envelope and wrapped it up in a bright magenta ribbon to make it presentable.

Cheerilee then wasted no time and made her way to Ponyville’s post office.

Chapter 2: Class is in Session

As he trotted happily to Ponyville Schoolhouse Mr. Starr couldn’t help grinning. This was an opportunity he couldn’t ignore. His chance to relive his glory days by storytelling them to a listening audience has come!

In addition, he could also pass down some maritime pointers to Miss Cheerilee’s students should one of them decide to pursue a life on the sea. Back in the old days, it was somewhat traditional to introduce your offspring to the maritime life to see if they wanted to follow in your hoof steps. Sadly, Mr. Starr never had any foals in his life, but that’s a story for another time.

Mr. Starr finally reached Ponyville Schoolhouse and knocked on the door. Almost immediately the door swung open to the sight of Cheerilee with a relieved smile on her muzzle.

“Oh thank you for coming, Mr. Starr. You’re arrival means so much to me right now.”

Mr. Starr couldn’t help but chuckle. “Of course, Miss Cheerilee. I wouldn’t dare miss this opportunity to educate youngsters of an age long past.”

The two ponies walked into the schoolhouse and Cheerilee offered Mr. Starr a chair right beside her desk, which he greatly accepted.

“So,” Cheerilee began, “First and foremost, thank you again for coming. Secondly, I have asked for your help regarding the last few weeks of this school year.” Miss Cheerilee went on and explained the whole ordeal to Mr. Starr: the assignment, the study, the presentation, etc. By the time Cheerilee finished, Mr. Starr was very surprised.

“Well, Miss Cheerilee,” the old stallion said with a smile, “You have come to the right stallion. I’m happy to say I have at least two decades of experience in the maritime business, and a more than extensive knowledge of tugboats. For I have once captained a small fleet of them for more than 15 years.”

Cheerilee was ecstatic. “That’s amazing! More than I expected but very impressive.”

Before Cheerilee could say more Mr. Starr interjected, “Is this lesson on the subject of tugboats alone? Or does the assignment revolve around their significance in the economy and influence on the public’s imagination?”

Cheerilee pondered on the question for a moment. She then responded, “I think a little bit of both.”

Mr. Starr grinned at that. “In that case, I happen to have an idea.”

“Do tell,” Cheerilee replied.

“I have a few stories worth sharing that heavily involves the tugboat fleet I mentioned earlier. While you handle the lessons and lectures and such, I shall share a tale or two of my younger days in Manehattan. They will act as a means of proving to your students the lesson you just lectured about to be effective towards the ponies of the past.”

Silence fell as Cheerilee considered Mr. Starr’s proposal. The more she thought about it the more she loved it. Not only would the stories be useful to specify certain lessons, but they would also double as an old-fashioned story time.

“I love it! The foals would never refuse a good story about Equestria’s past. Mr. Starr you are an absolute genius!”

Mr. Starr nearly blushed at that last comment. He was about to reply when he noticed Cheerilee’s face suddenly took on a slight frown. She looked back to Mr. Starr with a serious look in her eyes that made him think, “She’s about to say something that I can’t ignore.”

“Actually,” Cheerilee started with a tired look, “There are two students in my class that I should probably warn you about. They’re known to be cruel and cold to the other students, especially the ones who haven’t earned their cutie marks yet.”

Mr. Starr took Cheerilee’s words into great consideration. It was an unfortunate fact that countless colts and fillies across Equestria have fallen victim to bullies and harassers due to the lack of a mark resembling their life talents on their hindquarters. He himself was not an exception. He hated how some sweet young foals could turn into heartless attackers who preyed upon the mark-less.

Mr. Starr shook his head to avoid unwanted memories and continued listening to Cheerilee.

“Diamond Tiara has a record of being incredibly rude and disrespectful. She and her only friend, Silver Spoon, have had more reports of bullying and verbal cruelty than I wish to count. There are also times when Diamond can forget her manners and even lash out at ponies of other age groups.” Mr. Starr narrowed his eyes at that. “And worst of all, she is never shy of speaking her dislike of any subject I give to the class. On the very few occasions Diamond has minded her manners to a degree, but lately she has gotten worse. I feel the need to tell you-“

“If she gives me any lip,” Mr. Starr interrupted, “Or if she doesn’t care about me or my stories then that is her problem. One student’s cooperation isn’t worth that of the entire class.”

Cheerilee had to agree. All the same she reminded Mr. Starr to be careful.

The Next Day

The morning school bell rang to signify the star of a new school day. Monday wasn’t a favorite to the foals of Ponyville so most of them were still half asleep. Regardless, they made their way to their designated desks and waited patiently.

Cheerilee got down from her stool that helped her reach the bell’s rope and greeted her class. “Good morning, my little ponies.”

“Good morning, Miss Cheerilee,” the foals greeted back!

Cheerilee giggled behind her hoof. She loved hearing her students say that. “Right. Well, I hope you all had a good weekend. As we all know, there are eight weeks of school left before Summer Vacation-“ Cheerilee didn’t get to finish that sentence for the majority of the students cheered at that tidbit of information. Amongst the cheering was a barely audible “Like, about time!” from a certain pink filly wearing her signature headwear.

“Settle down. Settle down now,” Cheerilee called over the noise. After her students calmed down Cheerilee made her way to the chalkboard. “For the remainder of the school year I have decided to give all of you a special assignment that I’m sure you will enjoy.”

The little colts and fillies gazed at their teacher in wonder. A special assignment? An enjoyable one at that? Wonder what it could be? Cheerilee got to the chalkboard and turned around to address the class.

“Now, this assignment will have you doing something a little different. This final lesson will be covering a variety of attributes that we may have already gone over, or have yet to cover. These attributes will be coming from an unusual yet fitting topic, one which had a fascinating effect on Equestria’s history as of three decades ago.”

The class was amazed.

“As I already said, we might be revisiting some topics I have already taught while covering new ones at the same time. The assignment will be teaching the values of friendship, working together, the importance of trust and honesty, and most importantly, versatility.”

Dinky Doo raised her hoof. “What does… vers-til-aty… mean?”

It took a good amount of willpower for Cheerilee not to laugh at Dinky’s mispronouncing of the word. “Versatility, Dinky, is the ability to adapt or be adapted to many different functions or activities.”

A brown colt wearing a propeller beanie put his hoof up. “So, it’s another word for multitasking?”

“Not exactly, Button Mash,” replied Cheerilee. “It means that something designed for a specific task can be used for some different yet similar tasks at the same rate as its’ original usage.”

By this point Diamond Tiara was growing impatient. “So, like, what subject is it that we have to study?! Let’s get it over with and get done faster so we can, like, go home!”

Cheerilee kept her composure and took a deep breath before speaking again. “Diamond Tiara, need I remind you to be patient? I understand you all would like for summer to arrive but it doesn’t hurt to enjoy the remaining school year while it lasts.”

Diamond Tiara just rolled her eyes and muttered to herself, “Whatever” when she thought no pony could hear her. Cheerilee did, but chose to let it go this once.

“For this assignment the study topic shall be, the tugboat,” Cheerilee announced with glee!

An uncomfortable silence fell upon the entire room. Cheerilee saw some of her students look back at her with confusion, others with curiosity, while the rest looked just disappointed. Luckily, she was quick to speak up again before they began complaining.

“I know it might sound boring, but rest assured, there is a lot more to the tugboat than meets the eye. For example, tugboats are no ordinary workboat; they were designed to push and pull many times their own weight, were made to last, and surprisingly have left behind quite the effect on the imagination of ponies in the maritime business.”

For the next few hours Cheerilee went over the basic principles and protocols the tugboat follows, their origins, evolution throughput history and the like. All the while, her class were taking in the lecture in varying ways. A few were genuinely interested with this new subject, others just went along with it and took notes to show they were listening, while the rest barely listened without a care.

Eventually, it was time for lunch and recess. Cheerilee let her students outside and returned to her desk. She sat down and gone over her paperwork to pass the time. Cheerilee was so focused into her work she nearly jumped out of her skin when the door came open. She turned to the door quickly and saw it was none other than her special guest.

“Mr. Starr,” Cheerilee said, startled! “You frightened me.”

“Apologies, Miss Cheerilee. I got here right when you asked me; before 12:30.”

Cheerilee turned towards the clock and saw it was 12:25p.m. “Well then, it would seem that you have.”

“Your students all gave me surprised looks when I approached the building. I don’t think they recognize me yet.”

“Oh, don’t worry about it. I have had ponies come to my class to help with study sessions before. This is your first time here and I forgot to mention you were coming, so it’s understandable they were confused when you came. Go ahead and make yourself comfortable and I shall call the foals back in.”

Mr. Starr did just that and sat down in a spare chair while Cheerilee went to ring the bell.

Once all the foals were back inside and returned to their seats Cheerilee walked in front of her desk. “Welcome back, my little ponies. I’m sure you have seen a new arrival come in. I must apologize; I have forgotten to mention we have a guest speaker pony who has great knowledge and experience about our current study subject. So put on a happy face for Mr. Skipper Starr!”

The foals, except Diamond Tiara, politely applauded for Mr. Starr as he stood up and bowed his head slightly.

“Thank you for having me here,” Mr. Starr said to the class. “I hope to make good acquaintances with you. If any of you have questions don’t hesitate to ask.”

Applebloom raised her hoof and said, “Are ya’ll gonna teach us more about them tugboats?”

Mr. Starr chuckled slightly at the yellow filly’s accent. “Why yes, yes I am. In fact I plan to do more than just “teach” you about tugboats; that’s Miss Cheerilee’s job. I’ll save you my life story. Let’s just say I have at least twenty years of hooves-on experience with tugboats.”

Scootaloo raised her hoof next. “No offense, Mr. Starr, sir, but what more can you tell us about the tugboats? Cheerilee already went over their functions before lunch. Surely there can’t be more to know about.”

Mr. Starr only shook his head at the filly’s ignorance. “No offense taken, little lady. I can personally guarantee you that there is much, much more to the tugboat than what you already know.”

“Like what,” asked Sweetie Bell?

“How about you blank flanks shut up so he can, like, tell us,” Diamond Tiara burst out rudely!

Cheerilee was about to scold the spoiled pink filly but Mr. Starr beat her to the punch. “I understand you are excited, young filly…” Diamond Tiara looked dumbfounded by that comment. “…but I must ask that you not be so rude to your fellow classmates.”

The three fillies, who initially had scowls on their faces from Diamond Tiara’s rudeness, gave Mr. Starr grateful grins at stupefying the bully.

“As I was saying, I have a long history with tugboats and other maritime elements. I would like to share them with you.” The majority of the fillies and colts grew excited at the idea of a good story and leaned in with anticipation.

“Now, I know some of you might be thinking that tugboats only worked in harbors helping bigger ships and liners in and out of the busy port. Well let me tell you that is a large part of their duties, but they are also one the most versatile vessels ever built.

“You see, the tugboat, for its size, is the most powerful craft afloat. And my former fleet of tugs, the Star Fliers, were the power behind the docks and waterways that made up the Manehattan Port.

“This… is Tugs!”